O-(E)-Phenylbut-3-en-1-yl O-isopropyl thionocarbonate | 144302-93-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: O-(E)-Phenylbut-3-en-1-yl O-isopropyl thionocarbonate
• 英文别名: [(E)-4-phenylbut-3-enoxy]-propan-2-yloxymethanethione
• CAS: 144302-93-2
• 化学式: C₁₄H₁₈O₂S
• 分子量: 250.362
• InChiKey: WLJOURZHFBWAQC-UXBLZVDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  50.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (3E)-4-phenyl-3-buten-1-ol 、 N,N'-硫羰基二咪唑 、 异丙醇 生成 O-(E)-Phenylbut-3-en-1-yl O-isopropyl thionocarbonate
  参考文献：
  名称：

  Tributylstannane-mediated cyclization of thionocarboxylic acid derivatives

  摘要：

  Cyclization reactions of various thionoesters and thioamides involving the addition of tri-n-butylstannyl radical to a thiocarbonyl group and intramolecular addition of the resulting radical to a carbon-carbon multiple bond was studied. Dithiocarbonate and (imidazolyl)thiocarbonyl derivatives of homoallylic alcohols gave alpha-substituted gamma-thionobutyrolactones. The reaction is highly dependent on the substitution pattern on the double bond, a high yield of cyclic products being obtained only when the double bond is activated and unhindered. (Z)-4-Phenylbut-3-enyl thionobenzoate afforded 4,5-dihydro-2-phenyl-3-benzylfuran in low yield. In reactions involving a thioamide group, good yields of cyclic products were obtained only from compounds in which the electron density on the nitrogen atom is decreased by an electron attracting group. Cyclization of 1-((E)-4-phenylbut-3-en-1-yl)-5-thioxopyrrolidin-2-one (23) afforded 1-aza-4-benzylbicyclo[3.3.0]oct-4-en-8-one (33).

  DOI：

  10.1021/jo00051a024

文献信息

• Bachi Mario D., Bosch Eric, Denenmark Daniella, Girsh Diana, J. Org. Chem., 57 (1992) N 25, S 6803-6810
  作者：Bachi Mario D., Bosch Eric, Denenmark Daniella, Girsh Diana

  DOI：——

  日期：——
• Tributylstannane-mediated cyclization of thionocarboxylic acid derivatives
  作者：Mario D. Bachi、Eric Bosch、Daniella Denenmark、Diana Girsh

  DOI：10.1021/jo00051a024

  日期：1992.12

  Cyclization reactions of various thionoesters and thioamides involving the addition of tri-n-butylstannyl radical to a thiocarbonyl group and intramolecular addition of the resulting radical to a carbon-carbon multiple bond was studied. Dithiocarbonate and (imidazolyl)thiocarbonyl derivatives of homoallylic alcohols gave alpha-substituted gamma-thionobutyrolactones. The reaction is highly dependent on the substitution pattern on the double bond, a high yield of cyclic products being obtained only when the double bond is activated and unhindered. (Z)-4-Phenylbut-3-enyl thionobenzoate afforded 4,5-dihydro-2-phenyl-3-benzylfuran in low yield. In reactions involving a thioamide group, good yields of cyclic products were obtained only from compounds in which the electron density on the nitrogen atom is decreased by an electron attracting group. Cyclization of 1-((E)-4-phenylbut-3-en-1-yl)-5-thioxopyrrolidin-2-one (23) afforded 1-aza-4-benzylbicyclo[3.3.0]oct-4-en-8-one (33).