(9Z,11Z)-Retinol | 93380-02-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (9Z,11Z)-Retinol
• 英文别名: 9-cis-Retinol；(2E,4Z,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraen-1-ol
• CAS: 93380-02-0
• 化学式: C₂₀H₃₀O
• 分子量: 286.458
• InChiKey: FPIPGXGPPPQFEQ-IAGSAMJHSA-N

物化性质

• 沸点：
  421.2±14.0 °C(Predicted)
• 密度：
  0.954±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (9Z,11Z)-Retinol 在 吡啶 作用下， 以 正己烷 为溶剂， 生成 Acetic acid (1S,6S,7R,8S)-2,6-dimethyl-8-(2,6,6-trimethyl-cyclohex-1-enyl)-bicyclo[4.2.0]octa-2,4-dien-7-ylmethyl ester
  参考文献：
  名称：

  Preparation of (9Z, 11Z) - Vitamin A

  摘要：

  Starting from (7E,9Z)-C15-aldehyde 4, the syntheses of (9Z,11Z)-vitamin A acetate and palmitate are reported. The construction strategy is based on treatment of 4 with Zn-PPh3/CBr4, addition of acetaldehyde followed by a Wittig-Horner reaction to give the (9Z,11Z)-C20-nitrile 7 which was reduced with DIBAH to the corresponding aldehyde 8 and then to the title compound 1. The thermal instability of 1 is discussed.

  DOI：

  10.1016/s0040-4039(00)79877-7
• 作为产物：
  描述：

  (7E,9Z)-beta-离子亚基乙醛 在 正丁基锂 、 聚合甲醛 、 二异丁基氢化铝 、 三苯基膦 、 锌 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 生成 (9Z,11Z)-Retinol
  参考文献：
  名称：

  Preparation of (9Z, 11Z) - Vitamin A

  摘要：

  Starting from (7E,9Z)-C15-aldehyde 4, the syntheses of (9Z,11Z)-vitamin A acetate and palmitate are reported. The construction strategy is based on treatment of 4 with Zn-PPh3/CBr4, addition of acetaldehyde followed by a Wittig-Horner reaction to give the (9Z,11Z)-C20-nitrile 7 which was reduced with DIBAH to the corresponding aldehyde 8 and then to the title compound 1. The thermal instability of 1 is discussed.

  DOI：

  10.1016/s0040-4039(00)79877-7

文献信息

• Preparation of (9Z, 11Z) - Vitamin A
  作者：Peter Vogt、Markus Schlageter、Erich Widmer

  DOI：10.1016/s0040-4039(00)79877-7

  日期：1991.8

  Starting from (7E,9Z)-C15-aldehyde 4, the syntheses of (9Z,11Z)-vitamin A acetate and palmitate are reported. The construction strategy is based on treatment of 4 with Zn-PPh3/CBr4, addition of acetaldehyde followed by a Wittig-Horner reaction to give the (9Z,11Z)-C20-nitrile 7 which was reduced with DIBAH to the corresponding aldehyde 8 and then to the title compound 1. The thermal instability of 1 is discussed.