1-苯基硫代-2-辛烯 | 84019-03-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 中文名称: 1-苯基硫代-2-辛烯
• 英文名称: 1-phenylthio-2-octene
• 英文别名: oct-2-enylsulfanylbenzene
• CAS: 84019-03-4
• 化学式: C₁₄H₂₀S
• 分子量: 220.379
• InChiKey: AMQFEMIQXUHVPA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.92
• 重原子数：
  15.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  1-苯基硫代-2-辛烯 在 磺酰氯 、 水 、 copper(II) oxide 、 copper dichloride 作用下， 以 四氯化碳 、 丙酮 为溶剂， 反应 2.0h， 生成 2-辛烯醛
  参考文献：
  名称：

  Synthesis of α,β-Unsaturated Aldehydes and Methyl Carboxylic Esters from 2-Acetylenic Phenyl Sulfides.

  摘要：

  2-Alkynylthio benzenes were reduced to 2-Alkenylthio benzenes with diisobutyl aluminum hydride. Mono chlorination of these compounds with sulfuryl chloride and pyridine followed by hydrolysis, in the presence of Cu-II salts, gave alpha,beta-unsaturated aldehydes.2-Alkynylthio benzenes were converted into 2-Alkynyl 1,1-bis thiobenzenes by monochlorination with sulfuryl chloride and pyridine followed by treatment with thiophenol and triethylamine. These substances were then converted to alpha,beta-unsaturated methyl carboxylic esters by way of isomerization with sodium methoxide to the corresponding allene and treatment with hydrochloric acid and methanolysis in the presence of iodine.

  DOI：

  10.1080/00397919708005915
• 作为产物：
  描述：

  Oct-2-ynylsulfanyl-benzene 在 二异丁基氢化铝 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 2.0h， 以81%的产率得到1-苯基硫代-2-辛烯
  参考文献：
  名称：

  Synthesis of α,β-Unsaturated Aldehydes and Methyl Carboxylic Esters from 2-Acetylenic Phenyl Sulfides.

  摘要：

  2-Alkynylthio benzenes were reduced to 2-Alkenylthio benzenes with diisobutyl aluminum hydride. Mono chlorination of these compounds with sulfuryl chloride and pyridine followed by hydrolysis, in the presence of Cu-II salts, gave alpha,beta-unsaturated aldehydes.2-Alkynylthio benzenes were converted into 2-Alkynyl 1,1-bis thiobenzenes by monochlorination with sulfuryl chloride and pyridine followed by treatment with thiophenol and triethylamine. These substances were then converted to alpha,beta-unsaturated methyl carboxylic esters by way of isomerization with sodium methoxide to the corresponding allene and treatment with hydrochloric acid and methanolysis in the presence of iodine.

  DOI：

  10.1080/00397919708005915

文献信息

• Aprotic conjugate addition of allyllithium reagents bearing polar groups to cyclic enones. 1. 3-Alkylallyl systems
  作者：Malcolm R. Binns、Richard K. Haynes、Andrew G. Katsifis、Paul A. Schober、Simone C. Vonwiller

  DOI：10.1021/ja00224a029

  日期：1988.8

  regiochimie et de la stereochimie de l'addition conjuguee de sulfoxydes et d'oxydes de phosphine d'alcene-2yles, de phosphonates et de sulfoxydes d'allyles et de dimethyl-3,3 allyles, lithiees a des enones cycliques

  Etude de la regiochimie et de lastereochimie de l'addition conjuguee de sulfoxydes et d'oxydes de phosphine d'alcene-2yles, de phosphonates et de sulfoxydes d'allyles et de dimethyl-3,3 allyles, lithiees a des enones cycliques
• Regioselective Reaction of Allylic Carbanion Derived from 1-Phenylthio-2-octene with Conjugated Cyclopentenone Derivative and Synthesis of Prostaglandin E₁
  作者：Junzo Nokami、Toshio Ono、Atsunori Iwao、Shoji Wakabayashi

  DOI：10.1246/bcsj.55.3043

  日期：1982.9

  The reaction of the allylic carbanion derived from 1-phenylthio-2-octene with conjugated cyclopentenone derivatives in the presence of hexamethylphosphoric triamide (HMPA) regioselectively gave the 1,4 adduct at the α carbon of the allylic sulfide. The reaction was employed for the synthesis of prostaglandin E1.

  在六甲基磷酰三胺 (HMPA) 存在下，源自 1-苯硫基-2-辛烯的烯丙基碳负离子与共轭环戊烯酮衍生物反应，在烯丙基硫化物的 α 碳上区域选择性地生成 1,4 加合物。该反应用于合成前列腺素 E1。