(2Z,4Z,6E,8E)-3-[4-(dimethoxymethyl)phenyl]-7-methyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraen-1-ol | 550364-55-1

• 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: (2Z,4Z,6E,8E)-3-[4-(dimethoxymethyl)phenyl]-7-methyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraen-1-ol
• CAS: 550364-55-1
• 化学式: C₂₈H₃₈O₃
• 分子量: 422.608
• InChiKey: OEJOTYCJODISOD-YQZNAHTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2Z,4Z,6E,8E)-3-[4-(dimethoxymethyl)phenyl]-7-methyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraen-1-ol 在 barium permanganate 作用下， 以 二氯甲烷 为溶剂， 以23%的产率得到(2Z,4Z,6E,8E)-3-[4-(dimethoxymethyl)phenyl]-7-methyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenal
  参考文献：
  名称：

  Trienylboronic acid, a versatile coupling tool for retinoid synthesis; stereospecific synthesis of 13-aryl substituted (11Z)-retinal

  摘要：

  Trienylboronic acid 1a was prepared from iodotriene 3, which was coupled with (2Z,4Z)-3-aryl-5-iodo-2,4-pentadienol 9 by Suzuki coupling reaction to give geometrically pure 13-aryl substituted (11Z)-retinol 10. Oxidation of 10 gave 13-aryl substituted (11Z)-retinal 11. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00550-1
• 作为产物：
  描述：

  (E)-丁烯-3-炔基-2,6,6-三甲基-1-环己烯 在 四(三苯基膦)钯 氢氧化钾 、 正丁基锂 、 甲基镁三丁基锡烷 、 silver carbonate 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.67h， 生成 (2Z,4Z,6E,8E)-3-[4-(dimethoxymethyl)phenyl]-7-methyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraen-1-ol
  参考文献：
  名称：

  Trienylboronic acid, a versatile coupling tool for retinoid synthesis; stereospecific synthesis of 13-aryl substituted (11Z)-retinal

  摘要：

  Trienylboronic acid 1a was prepared from iodotriene 3, which was coupled with (2Z,4Z)-3-aryl-5-iodo-2,4-pentadienol 9 by Suzuki coupling reaction to give geometrically pure 13-aryl substituted (11Z)-retinol 10. Oxidation of 10 gave 13-aryl substituted (11Z)-retinal 11. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00550-1

文献信息

• Trienylboronic acid, a versatile coupling tool for retinoid synthesis; stereospecific synthesis of 13-aryl substituted (11Z)-retinal
  作者：Jun'ichi Uenishi、Katsuaki Matsui、Akimori Wada

  DOI：10.1016/s0040-4039(03)00550-1

  日期：2003.4

  Trienylboronic acid 1a was prepared from iodotriene 3, which was coupled with (2Z,4Z)-3-aryl-5-iodo-2,4-pentadienol 9 by Suzuki coupling reaction to give geometrically pure 13-aryl substituted (11Z)-retinol 10. Oxidation of 10 gave 13-aryl substituted (11Z)-retinal 11. (C) 2003 Elsevier Science Ltd. All rights reserved.