查看“︁1,3-丙二硫醇”︁的源代码

{{chembox|Verifiedfields=changed|Watchedfields=changed|verifiedrevid=477205579|Name=1,3-丙二硫醇|ImageFile=1,3-Propandithiol Structural Formula V1.svg|ImageSize=200px|ImageName=1,3-Propanedithiol|ImageFile1=1,3-Propanedithiol-3D-balls.png|ImageAlt1=1,3-Propanedithiol molecule|PIN=Propane-1,3-dithiol|OtherNames=1,3-二巯基丙烷|Section1={{Chembox Identifiers
| SMILES = SCCCS
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 44864
| ChemSpiderID = 13848090
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 1235209
| PubChem = 8013
| EC_number = 203-706-9
| UNNumber = 3336
| UNII = R4LUJ82U52
| InChI = 1/C3H8S2/c4-2-1-3-5/h4-5H,1-3H2
| InChIKey = ZJLMKPKYJBQJNH-UHFFFAOYAS
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C3H8S2/c4-2-1-3-5/h4-5H,1-3H2
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = ZJLMKPKYJBQJNH-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 109-80-8
| RTECS = TZ2585500
  }}|Section2={{Chembox Properties
| C=3 | H=8 | S=2
| Appearance = 無色液體
| Density = 1.078 g/cm<sup>3</sup>
| Solubility =微溶
| Solvent = solvents
| SolubleOther = 有機溶劑
| MeltingPtC = -79
| BoilingPtC = 169
| pKb =
| RefractIndex = 1.539
  }}|Section3={{Chembox Structure
| Dipole = 0 [[Debye|D]]
  }}|Section7={{Chembox Hazards
| MainHazards = stench
| FlashPtC = 138
| GHSPictograms = {{GHS07}}
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|302|315|319|335}}
| PPhrases = {{P-phrases|261|264|270|271|280|301+312|302+352|304+340|305+351+338|312|321|330|332+313|337+313|362|403+233|405|501}}
  }}|Section8=|OtherCompounds=[[乙二硫醇]]}}
'''1,3-丙二硫醇'''，又名'''1,3-二巰基丙烷'''，化學式<chem>C3H8S2</chem>，是一種[[有机化合物|有機化合物]]，[[硫醇]]的一種。常溫下是無色的液體<ref>{{Cite web |date=2022-01-11 |title=1,3-丙二硫醇 |url=https://www.chemsrc.com/cas/109-80-8_333505.html |website=化源網 |access-date=2022-08-24|quote=透明, 液体}}</ref>，有一種令人不愉快的氣味。微溶於水。<ref>{{Cite web |title=1,3-丙二硫醇 |url=https://www.chembk.com/cn/chem/1,3-%E4%B8%99%E4%BA%8C%E7%A1%AB%E9%86%87 |website=化工百科 |language=中文 |access-date=2022-08-24 |archive-date=2017-10-07 |archive-url=https://web.archive.org/web/20171007091742/http://www.chembk.com/cn/chem/1,3-%E4%B8%99%E4%BA%8C%E7%A1%AB%E9%86%87 |dead-url=no }}</ref>於[[有机合成|有機合成]]中是有用的試劑，可以保護[[醛]]和[[酮]]。

== 反應 ==

=== 有機反應 ===
1,3-丙二硫醇可以與[[醛]]、[[酮]]反應，可逆地生成[[1,3-二噻烷]]，因此它可以保護醛酮。<ref>{{cite encyclopedia|author1=Conrow, R. E.|author2=Le Huérou, Y.|title=1,3-Propanedithiol|encyclopedia=Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette)|year=2004|publisher=J. Wiley & Sons, New York|doi=10.1002/047084289X|hdl=10261/236866|hdl-access=free}}</ref>上[[保护基|保護基]]時，醛酮在[[酸]][[催化剂|催化劑]]（如[[三氟化硼]]）存在下與1,3-丙二硫醇作用即可，通常使用[[酸碱电子理论|路易斯酸]]而不是[[酸碱质子理论|質子酸]]。<ref>{{Cite book|title=Organic Chemistry|year=2012|url=https://archive.org/details/organicchemistry0000clay|last=Clayden|isbn=978-0-19-927029-3|pages=[https://archive.org/details/organicchemistry0000clay/page/662 662]|first=Jonathan|last2=Greeves|first2=Nick|last3=Warren|first3=Stuart|chapter=Chapter 27}}</ref>去除保護基時，除了可以用[[二價汞離子]]，也可以在[[碱|鹼]]性條件下使用[[碘]]將保護基脫除。<ref>{{Cite book|title=基礎有機化學|last=邢|first=其毅|year=2017|isbn=978-7-301-27943-4|location=北京|pages=1176|language=中文|chapter=第26章}}</ref>如果使用[[雷尼镍|雷尼鎳]]，則會[[氧化还原反应|還原]]成[[亞甲基]]。<ref name="March">Smith, M. B.; March, J. ''March's Advanced Organic Chemistry'' 5th ed., Wiley, New York, 2001, pp. 556.</ref>

1,3-丙二硫醇能夠參與[[科里－泽巴赫反应|科里－澤巴赫反應]]，將醛轉換成酮。首先醛與1,3-丙二硫醇反應生成1,3-二噻烷。由於硫可以穩定負離子，1,3-二噻烷擁有一定的酸性。之後它與[[正丁基锂|正丁基鋰]]作用，產生一個親核的碳，再與[[亲电体|親電試劑]]（如[[卤代烷烃|鹵代烷]]、[[环氧化合物|環氧化合物]]<ref>{{cite journal |last1=Williams |first1=David R. |last2=Sit |first2=Sing Yuen |date=1 May 1984 |title=Total synthesis of (+)-phyllanthocin |url= |journal=Journal of the American Chemical Society |volume=106 |issue=10 |pages=2949–2954 |doi=10.1021/ja00322a035 |access-date=}}</ref><ref>{{cite journal |last1=Smith |first1=Amos B. |last2=Xian |first2=Ming |date=11 January 2006 |title=Anion Relay Chemistry: An Effective Tactic for Diversity Oriented Synthesis |url= |journal=Journal of the American Chemical Society |volume=128 |issue=1 |pages=66–67 |doi=10.1021/ja057059w |pmid=16390124 |access-date=}}</ref>、酮、[[酰卤|酰鹵]]等）反應生成2-烷基-1,3-二噻烷。<ref name="Corey Seebach 1975">{{cite journal |last1=Seebach |first1=Dieter |author-link1=Dieter Seebach |last2=Corey |first2=Elias James |author-link2=Elias James Corey |date=1 January 1975 |title=Generation and synthetic applications of 2-lithio-1,3-dithianes |url= |journal=The Journal of Organic Chemistry |volume=40 |issue=2 |pages=231–237 |doi=10.1021/jo00890a018 |access-date=}}</ref>此物可透過[[氧化汞]]等試劑水解，得到酮。
[[File:Dithiane_chemistry.png|center|500x500px|二噻烷]]
這反應體現出[[极性转换|極性轉換]]。


=== 無機反應 ===
1,3-丙二硫醇可以跟金屬離子反應，產生[[螯合物|螯合環]]。例如，它可跟[[十二羰基三铁|十二羰基三鐵]]反應生成[[六羰基丙二硫醇二铁|六羰基丙二硫醇二鐵]]，反應式如下：<ref>{{cite journal |author1=Winter, A. |author2=Zsolnai, L. |author3=Huttner, G. |year=1982 |title=Zweikernige und dreikernige Carbonyleisenkomplexe mit 1,2- und 1,3-Dithiolatobrückenliganden |journal=Zeitschrift für Naturforschung |volume=37b |pages=1430–1436 |doi=}}</ref>

<chem>Fe3(CO)12 +  C3H6(SH)2 -> Fe2(S2C3H6)(CO)6 +  H2  +  Fe(CO)5 +  CO</chem>

== 參見 ==

* [[硫醇]]
* [[1,2-乙二硫醇]]

== 參考資料 ==
{{reflist}}


{{醇类似物}}
[[Category:硫醇]]
[[Category:有机化学试剂]]
[[Category:螯合配体]]