S-phenyl 2-iodo(thiopropanoate) | 120346-76-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯硫酚酯
• 英文名称: S-phenyl 2-iodo(thiopropanoate)
• 英文别名: S-phenyl 2-iodopropanethioate；S-phenyl α-iodothiopropionate
• CAS: 120346-76-1
• 化学式: C₉H₉IOS
• 分子量: 292.14
• InChiKey: NKMKXKKULZUEIK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  S-phenyl 2-iodo(thiopropanoate) 在 magnesium iodide 作用下， 以 乙醚 为溶剂， 反应 288.0h， 以67%的产率得到硫基丙酸苯酯
  参考文献：
  名称：

  由2-苯基磺酸-2-苯基硫代肟酸酯制备2-卤代S-苯基硫代酯。2-苯基磺酰基氧杂环丁烷的晶体结构

  摘要：

  1-苯磺酰基-1- phenylthioalkenes 8与高立体选择性为（制备ê在一个单釜法）异构体通过的反应苯基苯硫基甲基砜9与醛，随后消除。用叔丁基氢过氧化物锂对这些烯烃进行亲核环氧化，得到2-苯基磺酰基-2-苯基硫代肟酸酯4，为单一的非对映异构体，而未检测到苯硫基官能团的氧化。还可以通过用丁基锂处理苯磺酰基氧肟酮13，然后再用二苯基二硫化物来制备环氧乙烷，这使得可以制备3,3-二烷基2-苯基磺酰基-2-苯基硫代环氧乙烷。oxiranes 4与锂或卤化镁反应得到的2-卤代良好的收率小号-苯基硫酯5，6和7。通过用碘化镁进一步处理使2-卤代S-苯基硫代酯7脱碘。以类似的方式，也从相应的肟酸酯制备2-溴S甲基硫代酯15和2-溴Se-苯基硒酸酯17b。2-苯基磺酰氧杂环戊烷4b，13e和14b的X射线晶体结构，表明远离磺酰基的C-O键的一致延长，以及与磺酰基相邻的C-O键的显着缩短。

  DOI：

  10.1039/p19910003091
• 作为产物：
  描述：

  S-phenyl 2-bromopropanethioate 在 sodium iodide 作用下， 以 丙酮 为溶剂， 以63%的产率得到S-phenyl 2-iodo(thiopropanoate)
  参考文献：
  名称：

  Direct Carbon−Carbon Bond Formation via Reductive Soft Enolization: A Kinetically Controlled syn-Aldol Addition of α-Halo Thioesters and Enolizable Aldehydes

  摘要：

  The direct addition of enolizable aldehydes and alpha-halo thioesters to produce beta-hydroxy thioesters enabled by reductive soft enolization is reported. The transformation is operationally simple and efficient and has the unusual feature of giving high syn-selectivity, which is the opposite of that produced for (thio)esters under conventional conditions. Moreover, excellent diastereoselectivity results when a chiral nonracemic alpha-hydroxy aldehyde derivative is used.

  DOI：

  10.1021/ja1057407

文献信息

• Preparation of 1-phenylsulphonyl-1-phenylthio epoxide: Convenientprecursors to α-halo S-phenyl thio esters
  作者：Cheryl T. Hewkin、Richard F.W. Jackson、William Clegg

  DOI：10.1016/s0040-4039(00)80635-8

  日期：1988.1

  1-Phenylsulphonyl-1-phenylthio epoxides (3), readily prepared from aldehydes, react with lithium or magnesium halides to give high yields of the corresponding α-halo S-phenyl thio esters.

  由醛容易制备的1-苯基磺酰基-1-苯基硫代环氧化物（3）与卤化锂或卤化镁反应，得到高产率的相应的α-卤代S-苯基硫代酯。
• Efficient Radical Oxygenation of α-Iodocarboxylic Acid Derivatives
  作者：Nobuhiro Kihara、Cyril Ollivier、Philippe Renaud

  DOI：10.1021/ol990971n

  日期：1999.11.1

  [GRAPHICS]Treatment of alpha-iodocarboxylic acid derivatives with 2 equiv of triethylborane under oxygen atmosphere gives the corresponding a-hydroxy acid derivatives. This method is based on an iodine atom transfer from the ethyl radical, generated by the reaction of triethylborane and oxygen, with the alpha-iodocarbonyl compound. It offers several advantages over classical ionic substitution reactions: no elimination product is observed, tertiary iodides are efficiently converted to alcohols, and finally, this one-step procedure is working with substrates sensitive to nucleophiles.
• HEWKIN, CHERYL T.;JACKSON, RICHARD F. W.;CLEGG, WILLIAM, TETRAHEDRON LETT., 29,(1988) N 38, C. 4889-4892
  作者：HEWKIN, CHERYL T.、JACKSON, RICHARD F. W.、CLEGG, WILLIAM

  DOI：——

  日期：——
• POLYVALENT CHIMERIC OSPC VACCINOGEN AND DIAGNOSTIC ANTIGEN
  申请人：Virginia Commonwealth University

  公开号：US20160097768A1

  公开（公告）日：2016-04-07

  Chimeric polyvalent recombinant proteins for use as vaccines and diagnostics for Lyme disease (e.g. in canines and humans) are provided. The chimeric proteins comprise epitopes of the loop 5 region and/or the alpha helix 5 region of outer surface protein C (OspC) types and/or OspE types. The OspC types may be associated with mammalian Borrelia infections.