查看“︁N,N'-二环己基碳二亚胺”︁的源代码

{{DISPLAYTITLE:''N'',''N'''-二環己基碳二亞胺}}
{{Chembox
|   Name = 二環己基碳二亞胺
|   ImageFile = DCC Structure.png
<!-- | ImageSize = 150px -->
|   ImageName = 二環己基碳二亞胺
|   ImageFile1 = DCC-3D-balls.png
<!-- | ImageSize1 = 150px  -->
|  ImageFile2 = Dicyclohexylcarbodiimide.png
|   IUPACName = N,N'-dicyclohexylcarbodiimide
|   OtherNames = ''N'',''N'''-二環己基碳二亞胺<br />碳二亞胺、DCC
|Section1={{Chembox Identifiers
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 53090
| SMILES = N(=C=N\C1CCCCC1)\C2CCCCC2
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 10408
| PubChem = 10868
| InChI = 1/C13H22N2/c1-3-7-12(8-4-1)14-11-15-13-9-5-2-6-10-13/h12-13H,1-10H2
| InChIKey = QOSSAOTZNIDXMA-UHFFFAOYAO
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 162598
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = QOSSAOTZNIDXMA-UHFFFAOYSA-N
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C13H22N2/c1-3-7-12(8-4-1)14-11-15-13-9-5-2-6-10-13/h12-13H,1-10H2
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 538-75-0
| RTECS = FF2160000
  }}
|Section2 = {{Chembox Properties
|   Formula = C<sub>13</sub>H<sub>22</sub>N<sub>2</sub>
|   MolarMass = 206.33 
|   Appearance = 白色晶体粉末
|   Density = 1.325 g/cm<sup>3</sup> (固)
|   Solubility = 不可溶
|   MeltingPt = 34&nbsp;°C (307 K)
|   BoilingPt = 122&nbsp;°C (395 K)
  }}
| Section7 = {{Chembox Hazards
|   ExternalMSDS =
|   NFPA-H = 3
|   NFPA-F = 1
|   NFPA-R =
|   FlashPt = 113&nbsp;°C
|   RPhrases = {{R22}}, {{R24}}, {{R41}}, {{R43}}
|   SPhrases = {{S24}}, {{S26}}, {{S37/39}}, {{S45}}
  }}
| Section8 = {{Chembox Related
|   Function = 
|   OtherFunctn = 
  }}
}}

'''''N'',''N'''-二環己基碳二亞胺'''（簡稱為'''DCC'''）是一個常用的脫水劑，化學式為C<sub>13</sub>H<sub>22</sub>N<sub>2</sub>，在[[多肽合成]]時尤其重要。

== 性质 ==
白色有气味的晶体，熔点很低，可溶于[[二氯甲烷]]、[[四氢呋喃]]、[[乙腈]]和[[二甲基甲酰胺]]，但不溶于水。

分子中的C-N=C=N-C一部分不是平面结构，为正交排列，类似于[[丙二烯]]。它有以下[[共振式]]： 
:<math>\rm \ RN\!=\!C\!=\!NR \leftrightarrow RN^+\! \equiv \!C\!-\!N^-R \leftrightarrow RN^-\!-\!C \! \equiv \!N^+R</math>

== 合成 ==
DCC的制取方法有：

1、[[环己胺]]和环己基[[异腈]]在[[乙酸钯]]、[[碘]]和氧气作用下，[[偶联]]生成DCC，<ref>{{Cite journal |last=Pri-Bar |first=Ilan |last2=Schwartz |first2=Jeffrey |title=N,N-Dialkylcarbodiimide synthesis bypalladium-catalysed coupling of amines with isonitriles |url=https://pubs.rsc.org/en/content/articlelanding/1997/cc/a606012i |journal=Chemical Communications |language=en |date=1997-01-01 |issue=4 |page=347 |doi=10.1039/A606012I |issn=1364-548X |access-date=2025-02-01 |archive-date=2024-06-15 |archive-url=https://web.archive.org/web/20240615042736/https://pubs.rsc.org/en/content/articlelanding/1997/cc/a606012i |dead-url=no }}</ref>产率可达67%：
: <math>\rm \ C_6H_{11}NC + C_6H_{11}NH_2 + O_2 \rightarrow (C_6H_{11}N)_2C + H_2O</math>

2、两分子环己基[[异氰酸酯]]在OP(MeNCH<sub>2</sub>CH<sub>2</sub>)<sub>3</sub>N催化下缩合生成DCC，产率92%：<ref name="tang">{{Cite journal |last=Tang |first=Jiansheng |last2=Mohan |first2=Thyagarajan |last3=Verkade |first3=John G. |title=Selective and Efficient Syntheses of Perhydro-1,3,5-triazine-2,4,6-triones and Carbodiimides from Isocyanates Using ZP(MeNCH2CH2)3N Catalysts |url=https://pubs.acs.org/doi/abs/10.1021/jo00096a041 |journal=The Journal of Organic Chemistry |date=1994-08-01 |volume=59 |issue=17 |page=4931-4938 |doi=10.1021/jo00096a041 |issn=0022-3263 |access-date=2025-02-01 |archive-date=2023-04-09 |archive-url=https://web.archive.org/web/20230409143247/https://pubs.acs.org/doi/abs/10.1021/jo00096a041 |dead-url=no }}</ref>

[[File:DCC synthesis from cyclohexyl isocyanate.svg|center|600px]]

3、两分子环己胺与[[二硫化碳]]缩合生成二环己基[[硫脲]]，再用[[氧化汞]]处理得到DCC：

[[File:DCC synthesis from cyclohexylamine.svg|center|650px]]

4、[[二环己基脲]]与芳基[[磺酰氯]]、[[碳酸钾]]和氯化苄基三乙基铵（[[相转移催化剂]]）反应生成DCC：<ref>{{Cite journal |last=Jászay |first=Zsuzsa M. |last2=Petneházy |first2=Imre |last3=Töke |first3=László |last4=Szajáni |first4=Béla |title=Preparation of Carbodiimides Using Phase-Transfer Catalysis |url=https://www.thieme-connect.de/products/ejournals/abstract/10.1055/s-1987-27992 |journal=Synthesis |language=en |date=1987 |volume=1987 |issue=05 |page=520-523 |doi=10.1055/s-1987-27992 |issn=0039-7881 |access-date=2025-02-01 |archive-date=2024-06-10 |archive-url=https://web.archive.org/web/20240610053732/https://www.thieme-connect.de/products/ejournals/abstract/10.1055/s-1987-27992 |dead-url=no }}</ref>

[[File:DCC synthesis.svg|750px|center|均相催化]]

== 反应 ==
二环己基碳二亚胺作失水剂，可用于[[酰胺]]、[[腈]]和[[酮]]的合成，自身转化为同样不溶于水的[[二环己基脲]]（DCU）。它也可使二级[[醇]]发生[[构型翻转]]。

[[Pfitzner-Moffatt氧化反应|Moffatt氧化]]：DCC和[[二甲基亚砜]]（DMSO）的混合溶液是[[Pfitzner-Moffatt氧化反应]]的氧化剂，可以将[[醇]]氧化为[[醛]]/[[酮]]。反应控制在醛一步，不生成羧酸。

[[File:DCC-DMSO oxidation of ethanol.svg|480px|center]]


[[失水]]：DCC使[[醇]]失水，经由''O''-酰基硫脲中间体，生成[[烯烃]]。<math>\rm \ RCHOHCH_2R' + (C_6H_{11}N)_2C \rightarrow RCH\!=\!CHR' +(C_6H_{11}NH)_2CO</math>

[[构型翻转]]：二级醇与DCC和[[甲醛]]混合得到甲酸酯类，再用[[甲醇钠]]之类的碱处理，发生[[皂化反应]]，得到发生构型翻转的醇。

[[酯化]]：DCC和催化量的[[4-二甲氨基吡啶]]（DMAP）作用下，醇（包括一些三级醇）可与羧酸发生[[酯化反应]]。<ref>{{OrgSynth |  title = Esterification of Carboxylic Acids with Dicyclohexylcarbodiimide/4-Dimethylaminopyridine: Tert-Butyl Ethyl Fumarate | author = B. Neises, W. Steiglich | collvol = 7 | collvolpages = 93 | year = 1990 | prep = cv7p0093}}</ref>

== 多肽合成 ==
使用失水剂DCC是除活化[[羧基]]外，另一个比较重要的[[多肽合成|接肽]]的方法。首先用[[苄氧羰基]]、[[叔丁氧羰基]]等[[保护基]]保护[[氨基]]，用[[酯]]类保护[[羧基]]，并将侧链保护起来。然后让反应物与DCC作用，两个底物缩合成目标多肽，DCC转化为二环己基脲。最后用[[钯碳|Pd-C]]催化[[氢化]]除去保护基，就得到游离的二肽。

== 参见 ==
* [[碳二亚胺]]：[[N,N'-二异丙基碳二亚胺]]、[[1-(3-二甲氨基丙基)-3-乙基碳二亚胺]]

== 参考资料 ==
{{reflist}}

== 外部链接 ==
* [http://chemistry2.csudh.edu/rpendarvis/AmAcSeqSyn.html 多肽的测序和合成]{{Wayback|url=http://chemistry2.csudh.edu/rpendarvis/AmAcSeqSyn.html |date=20050313052228 }}{{en icon}}

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[[Category:脱水剂]]
[[Category:肽偶联试剂]]
[[Category:碳二亚胺]]
[[Category:生物化学]]
[[Category:生物化学方法]]
[[Category:生物化学试剂]]
[[Category:环己基化合物]]
[[Category:过敏学]]