phenyl 4-bromo-2-butenyl sulfide

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: phenyl 4-bromo-2-butenyl sulfide
• 英文别名: 4-bromobut-2-enylsulfanylbenzene
• 化学式: C₁₀H₁₁BrS
• 分子量: 243.167
• InChiKey: OMUHHIDKPLKODY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.73
• 重原子数：
  12.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  phenyl 4-bromo-2-butenyl sulfide 在 盐酸 、 N,N-二甲基丙烯基脲 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 为溶剂， 生成 Ethyl 2-formamido-6-(phenylthio)hex-4-enoate
  参考文献：
  名称：

  Thiol Mediated Free Radical Cyclization of Alkenyl and Alkynyl Isocyanides

  摘要：

  Thiol-mediated free radical cyclizations of but-3-enyl and but-3-ynyl isocyanides of types 6-8 give new access to 3,5-disubstituted 2-(alkyl- and 2-(arylthio)pyrrolines 11, 12, and 18. When 2-mercaptoethanol is used with the same isocyanides the reaction results in pyroglutamates 16, 17, or 19. These cyclizations involve the formation of a new carbon-carbon bond through intramolecular addition of a carbon-centered thioimidoyl radical to a carbon-carbon multiple bond. Although cyclic products are usually obtained in high yields, in a few cases a competing radical degradation process leading to isothiocyanates was observed. Isocyanide 8a carrying an allyl(phenyl) sulfide moiety isomerizes to 2-(phenylthio)pyrroline 24 in a series of sequential steps.

  DOI：

  10.1021/jo00104a035
• 作为产物：
  描述：

  1,4-二溴-2-丁烯 、 苯硫酚 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 生成 phenyl 4-bromo-2-butenyl sulfide
  参考文献：
  名称：

  含氯胺-T的烯丙基硫化物的无催化剂亚胺化和随后的[2,3]-适马重排

  摘要：

  在没有金属催化剂的情况下，已经实现了基于烯丙基硫化物的氯胺-T酰亚胺化和随后的[2,3]-σ重排的轻松合成各种烯丙基磺酰胺的方法。反应在10分钟内顺利完成，在环境友好的乙醇溶剂中提供优异的收率。在这种条件下，溴，羟基，受保护的酰胺基和醛等官能团是可以耐受的。

  DOI：

  10.1002/cjoc.201200604

文献信息

• Total synthesis of (.+-.)-N2-(phenylsulfonyl)-CPI, (.+-.)-CC-1065, (+)-CC-1065, ent-(-)-CC-1065, and the precise, functional agents (.+-.)-CPI-CDPI2, (+)-CPI-CDPI2, and (-)-CPI-CDPI2 [(.+-.)-(3bR*,4aS*)-, (+)-(3bR,4aS)-, and (-)-(3bS,4aR)-deoxy-CC-1065]
  作者：Dale L. Boger、Robert S. Coleman

  DOI：10.1021/ja00222a043

  日期：1988.7

  CPI correspond a un derive de cyclopropa [c] pyrrolo [3,2-e] indole et CDPI 2 , correspond a un derive de carbonyl-2,3p bis-benzo [1,2-b:4,3-b'] dipyrrole

  CPI 对应一个联合国衍生的 de cyclopropa [c] pyrrolo [3,2-e] indole et CDPI 2 ，对应一个 un衍生 de carbonyl-2,3p 双苯并 [1,2-b:4,3-b']双吡咯
• Catalyst-Free Imidation of Allyl Sulfides with Chloramine-T and Subsequent [2,3]-Sigmatropic Rearrangement
  作者：Yubo Jiang、Fanyang Mo、Di Qiu、Chunxiang Kuang、Yan Zhang、Jianbo Wang

  DOI：10.1002/cjoc.201200604

  日期：2012.9

  A facile synthesis of various allyl sulfonamides based on imidation of allyl sulfides with chloramine‐T and subsequent [2,3]‐sigmatropic rearrangement has been achieved without metal catalysts. The reaction completes smoothly within 10 min, providing excellent yields in environment friendly solvent of alcohol. Functional groups such as bromine, hydroxyl, protected amido and aldehyde are tolerant under

  在没有金属催化剂的情况下，已经实现了基于烯丙基硫化物的氯胺-T酰亚胺化和随后的[2,3]-σ重排的轻松合成各种烯丙基磺酰胺的方法。反应在10分钟内顺利完成，在环境友好的乙醇溶剂中提供优异的收率。在这种条件下，溴，羟基，受保护的酰胺基和醛等官能团是可以耐受的。
• Thiol Mediated Free Radical Cyclization of Alkenyl and Alkynyl Isocyanides
  作者：Mario D. Bachi、Anna Balanov、Nira Bar-Ner

  DOI：10.1021/jo00104a035

  日期：1994.12

  Thiol-mediated free radical cyclizations of but-3-enyl and but-3-ynyl isocyanides of types 6-8 give new access to 3,5-disubstituted 2-(alkyl- and 2-(arylthio)pyrrolines 11, 12, and 18. When 2-mercaptoethanol is used with the same isocyanides the reaction results in pyroglutamates 16, 17, or 19. These cyclizations involve the formation of a new carbon-carbon bond through intramolecular addition of a carbon-centered thioimidoyl radical to a carbon-carbon multiple bond. Although cyclic products are usually obtained in high yields, in a few cases a competing radical degradation process leading to isothiocyanates was observed. Isocyanide 8a carrying an allyl(phenyl) sulfide moiety isomerizes to 2-(phenylthio)pyrroline 24 in a series of sequential steps.