9,13-bis-demethylretinol | 4939-51-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 9,13-bis-demethylretinol
• 英文别名: 9.13-Didesmethylretinol；(2E,4E,6E,8E)-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraen-1-ol
• CAS: 4939-51-9
• 化学式: C₁₈H₂₆O
• 分子量: 258.404
• InChiKey: OJFYOKNOYLOKBN-IGEUGCNCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 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：

  9,13-bis-demethylretinol 在 manganese(IV) oxide 作用下， 生成 all-trans-9,13-demethyl-retinal
  参考文献：
  名称：

  Series of synthetic visual pigments from cattle opsin and homologs of retinal

  摘要：

  DOI：

  10.1021/ja01049a069
• 作为产物：
  描述：

  [(1E,3E)-5-hydroxypenta-1,3-dien-1-yl]boronic acid 在 sodium hydroxide 、 四(三苯基膦)钯 、 氢氧化铊(Ⅰ) 、 碘 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 0.75h， 生成 9,13-bis-demethylretinol
  参考文献：
  名称：

  The suzuki reaction in stereocontrolled polyene synthesis: Retinol (vitamin A), its 9- and/or 13-demethyl analogs, and related 9-demethyl-dihydroretinoids

  摘要：

  A new synthesis of retinol (vitamin A) and 9- and/or 13-demethylretinols, with essentially complete control of regio- and stereochemistry, is described which is based on the thallium-accelerated, palladium-catalyzed cross-coupling reactions of (E)-1-alkenylboronic acids and (E)-1-alkenyl iodides (Suzuki reaction). The procedure has also been extended to the stereocontrolled synthesis of a series of 9-demethyl-dihydroretinoids of potential biological interest.

  DOI：

  10.1016/0040-4020(94)01108-c

文献信息

• The suzuki reaction in stereocontrolled polyene synthesis: Retinol (vitamin A), its 9- and/or 13-demethyl analogs, and related 9-demethyl-dihydroretinoids
  作者：Alicia Torrado、Beatriz Iglesias、Susana López、Angel R. de Lera

  DOI：10.1016/0040-4020(94)01108-c

  日期：1995.2

  A new synthesis of retinol (vitamin A) and 9- and/or 13-demethylretinols, with essentially complete control of regio- and stereochemistry, is described which is based on the thallium-accelerated, palladium-catalyzed cross-coupling reactions of (E)-1-alkenylboronic acids and (E)-1-alkenyl iodides (Suzuki reaction). The procedure has also been extended to the stereocontrolled synthesis of a series of 9-demethyl-dihydroretinoids of potential biological interest.
• Series of synthetic visual pigments from cattle opsin and homologs of retinal
  作者：Paul E. Blatz、Mow Lin、Padma Balasubramaniyan、V. Balasubramaniyan、Peter B. Dewhurst

  DOI：10.1021/ja01049a069

  日期：1969.10