(E)-3-<(1'S,6'S)-(2',2',6'-trimethylcyclohex-1'-yl)>prop-2-enal | 163439-34-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-3-<(1'S,6'S)-(2',2',6'-trimethylcyclohex-1'-yl)>prop-2-enal
• 英文别名: (E)-3-[(1S,6S)-2,2,6-trimethylcyclohexyl]prop-2-enal
• CAS: 163439-34-7
• 化学式: C₁₂H₂₀O
• 分子量: 180.29
• InChiKey: UKIHFUQJXXELDW-KKSDUGGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-3-<(1'S,6'S)-(2',2',6'-trimethylcyclohex-1'-yl)>prop-2-enal 在 chromium dichloride 、 sodium hydroxide 、 四(三苯基膦)钯 、 氢氧化铊(Ⅰ) 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 生成 (5S,6S)-9-demethyl-5,6-dihydroretinol
  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
• 作为产物：
  描述：

  (E)-3-((S)-2,2,6-Trimethyl-cyclohexyl)-prop-2-en-1-ol 在 manganese(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以81%的产率得到(E)-3-<(1'S,6'S)-(2',2',6'-trimethylcyclohex-1'-yl)>prop-2-enal
  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.