11-cis-4-Hydroxyretinol | 228122-02-9

• 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: 11-cis-4-Hydroxyretinol
• 英文别名: 3-[(1E,3E,5Z,7E)-9-hydroxy-3,7-dimethylnona-1,3,5,7-tetraenyl]-2,4,4-trimethylcyclohex-2-en-1-ol
• CAS: 228122-02-9
• 化学式: C₂₀H₃₀O₂
• 分子量: 302.457
• InChiKey: IOELQUUUYMBPSA-SSFHJJDOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 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：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  11-cis-4-Hydroxyretinol 在 manganese(IV) oxide 作用下， 以75%的产率得到11-cis-4-Oxoretinal
  参考文献：
  名称：

  Efficient Synthesis of 11-cis-Retinoids

  摘要：

  The light sensitivity and unstable nature of 11-cis-retinoids makes them ideal visual chromophores in nature. The synthesis of 11-cis-retinal analogues is of paramount importance in bioorganic studies of rhodopsin, the photoreceptor of the visual transduction pathway, but the instability of 11-cis-retinoids complicates their synthesis and there is no general synthetic route. Common strategies to the cis geometry have failed in the case of 11-cis-retinoids, and most often low yields and complex isomeric mixtures are obtained. Herein we report an efficient, general, and mild preparation of 11-cis-retinoids by semi-hydrogenation of 11-yne-retinoid precursors with Cu/Ag-activated zinc dust.

  DOI：

  10.1002/(sici)1521-3765(19990401)5:4<1172::aid-chem1172>3.0.co;2-q
• 作为产物：
  描述：

  (E)-4-(2,6,6-trimethyl-3-triethylsilyloxycyclohexen-1-yl)but-3-en-2-one 在 copper(l) iodide 、 四(三苯基膦)钯 正丁基锂 、 四丁基氟化铵 、 水 、 银 、 铜 、 异丙胺 、 锌 作用下， 以 四氢呋喃 、 异丙醇 为溶剂， 反应 8.75h， 生成 11-cis-4-Hydroxyretinol
  参考文献：
  名称：

  Efficient Synthesis of 11-cis-Retinoids

  摘要：

  The light sensitivity and unstable nature of 11-cis-retinoids makes them ideal visual chromophores in nature. The synthesis of 11-cis-retinal analogues is of paramount importance in bioorganic studies of rhodopsin, the photoreceptor of the visual transduction pathway, but the instability of 11-cis-retinoids complicates their synthesis and there is no general synthetic route. Common strategies to the cis geometry have failed in the case of 11-cis-retinoids, and most often low yields and complex isomeric mixtures are obtained. Herein we report an efficient, general, and mild preparation of 11-cis-retinoids by semi-hydrogenation of 11-yne-retinoid precursors with Cu/Ag-activated zinc dust.

  DOI：

  10.1002/(sici)1521-3765(19990401)5:4<1172::aid-chem1172>3.0.co;2-q

文献信息

• Efficient Synthesis of 11-cis-Retinoids
  作者：Babak Borhan、María L. Souto、Joann M. Um、Bishan Zhou、Koji Nakanishi

  DOI：10.1002/(sici)1521-3765(19990401)5:4<1172::aid-chem1172>3.0.co;2-q

  日期：1999.4.1

  The light sensitivity and unstable nature of 11-cis-retinoids makes them ideal visual chromophores in nature. The synthesis of 11-cis-retinal analogues is of paramount importance in bioorganic studies of rhodopsin, the photoreceptor of the visual transduction pathway, but the instability of 11-cis-retinoids complicates their synthesis and there is no general synthetic route. Common strategies to the cis geometry have failed in the case of 11-cis-retinoids, and most often low yields and complex isomeric mixtures are obtained. Herein we report an efficient, general, and mild preparation of 11-cis-retinoids by semi-hydrogenation of 11-yne-retinoid precursors with Cu/Ag-activated zinc dust.