(2S,3S)-2-<(E,E)-4'-iodobuta-1',3'-dien-1'-yl>-1,1,3-trimethylcyclohexane | 163395-66-2

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: (2S,3S)-2-<(E,E)-4'-iodobuta-1',3'-dien-1'-yl>-1,1,3-trimethylcyclohexane
• 英文别名: (2S,3S)-2-[(1E,3E)-4-iodobuta-1,3-dienyl]-1,1,3-trimethylcyclohexane
• CAS: 163395-66-2
• 化学式: C₁₃H₂₁I
• 分子量: 304.214
• InChiKey: VLEGNCWUDJKWKI-QBLZOVDMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (2S,3S)-2-<(E,E)-4'-iodobuta-1',3'-dien-1'-yl>-1,1,3-trimethylcyclohexane 在 manganese(IV) oxide 、 四(三苯基膦)钯 、 氢氧化铊(Ⅰ) 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 13.0h， 生成 (5S,6S)-9-demethyl-5,6-dihydroretinal
  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 chromium dichloride 、 manganese(IV) oxide 、 sodium hydroxide 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 生成 (2S,3S)-2-<(E,E)-4'-iodobuta-1',3'-dien-1'-yl>-1,1,3-trimethylcyclohexane
  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.