1-(Phenylthio)-1,5-hexadien-3-ol | 63540-13-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 1-(Phenylthio)-1,5-hexadien-3-ol
• 英文别名: (1E)-1-phenylsulfanylhexa-1,5-dien-3-ol
• CAS: 63540-13-6
• 化学式: C₁₂H₁₄OS
• 分子量: 206.309
• InChiKey: SMDGZIKLIAGSAL-MDZDMXLPSA-N

物化性质

• 沸点：
  346.9±42.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  45.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(Phenylthio)-1,5-hexadien-3-ol 、 碘甲烷 在 氢氧化钾 作用下， 以50%的产率得到1-(Phenylthio)-3-methoxy-1,5-heptadiene
  参考文献：
  名称：

  Use of Hine's D Values To Predict the Position of the Equilibrium in the Cope Rearrangement of Multiply Substituted 1,5-Dienes

  摘要：

  A series of 1,5-dienes (1a-f) were employed to test whether Hine's D values can predict the position of equilibrium in Cope rearrangements. In the cases of the substituent pairs [OCH3, H], [OCH3, CH3], [N(CH3)(2), H], [N(CH3)(2), CH3], and [N(CH3)(2), OCH3], equilibrium constants calculated with Hine's D values gave reasonable agreement with those obtained experimentally. Dienes 1g-i were prepared to test whether reduction of the pi-donating character of a nitrogen substituent (carbamoyl vs dimethylamino) would change the directing ability of the nitrogen group. The aggregate order of directing ability was N(CH3)(2) > OCH3 > EtO(2)CN(CH3) > CH3 > A. Diene 15a, with a more complicated substitution pattern (OCH3 and CH3 versus CH3 and H) not directly amenable to analysis with D values, can be considered to reduce to the case of [OCH3, H]. The experimental K-eq obtained agreed with that expected for the [OCH3, H] pair. Dienes 15c and 16b, designed to test the pairs [CH3, SPh] and [OCH3, SPh], respectively, decomposed under the gas phase conditions of the rearrangement. Attempts to effect rearrangement with Pd(II) catalysis failed.

  DOI：

  10.1021/jo00128a019
• 作为产物：
  描述：

  3-(phenylthio)propenal 、 烯丙基溴化镁 生成 1-(Phenylthio)-1,5-hexadien-3-ol
  参考文献：
  名称：

  Use of Hine's D Values To Predict the Position of the Equilibrium in the Cope Rearrangement of Multiply Substituted 1,5-Dienes

  摘要：

  A series of 1,5-dienes (1a-f) were employed to test whether Hine's D values can predict the position of equilibrium in Cope rearrangements. In the cases of the substituent pairs [OCH3, H], [OCH3, CH3], [N(CH3)(2), H], [N(CH3)(2), CH3], and [N(CH3)(2), OCH3], equilibrium constants calculated with Hine's D values gave reasonable agreement with those obtained experimentally. Dienes 1g-i were prepared to test whether reduction of the pi-donating character of a nitrogen substituent (carbamoyl vs dimethylamino) would change the directing ability of the nitrogen group. The aggregate order of directing ability was N(CH3)(2) > OCH3 > EtO(2)CN(CH3) > CH3 > A. Diene 15a, with a more complicated substitution pattern (OCH3 and CH3 versus CH3 and H) not directly amenable to analysis with D values, can be considered to reduce to the case of [OCH3, H]. The experimental K-eq obtained agreed with that expected for the [OCH3, H] pair. Dienes 15c and 16b, designed to test the pairs [CH3, SPh] and [OCH3, SPh], respectively, decomposed under the gas phase conditions of the rearrangement. Attempts to effect rearrangement with Pd(II) catalysis failed.

  DOI：

  10.1021/jo00128a019

文献信息

• Junjappa, H.; Ila, H., Phosphorus, Sulfur and Silicon and the Related Elements, 1994, vol. 96, # 1-4, p. 35 - 54
  作者：Junjappa, H.、Ila, H.

  DOI：——

  日期：——
• Use of Hine's D Values To Predict the Position of the Equilibrium in the Cope Rearrangement of Multiply Substituted 1,5-Dienes
  作者：James P. Hagen、Kemberly D. Lewis、Scott W. Lovell、Paolo Rossi、Ayse Z. Tezcan

  DOI：10.1021/jo00128a019

  日期：1995.11

  A series of 1,5-dienes (1a-f) were employed to test whether Hine's D values can predict the position of equilibrium in Cope rearrangements. In the cases of the substituent pairs [OCH3, H], [OCH3, CH3], [N(CH3)(2), H], [N(CH3)(2), CH3], and [N(CH3)(2), OCH3], equilibrium constants calculated with Hine's D values gave reasonable agreement with those obtained experimentally. Dienes 1g-i were prepared to test whether reduction of the pi-donating character of a nitrogen substituent (carbamoyl vs dimethylamino) would change the directing ability of the nitrogen group. The aggregate order of directing ability was N(CH3)(2) > OCH3 > EtO(2)CN(CH3) > CH3 > A. Diene 15a, with a more complicated substitution pattern (OCH3 and CH3 versus CH3 and H) not directly amenable to analysis with D values, can be considered to reduce to the case of [OCH3, H]. The experimental K-eq obtained agreed with that expected for the [OCH3, H] pair. Dienes 15c and 16b, designed to test the pairs [CH3, SPh] and [OCH3, SPh], respectively, decomposed under the gas phase conditions of the rearrangement. Attempts to effect rearrangement with Pd(II) catalysis failed.