(Z)-3-[4-(dimethoxymethyl)phenyl]pent-2-en-4-yn-1-ol | 550364-52-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: (Z)-3-[4-(dimethoxymethyl)phenyl]pent-2-en-4-yn-1-ol
• CAS: 550364-52-8
• 化学式: C₁₄H₁₆O₃
• 分子量: 232.279
• InChiKey: FTSUBQJXHHCOJS-LUAWRHEFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  (Z)-3-[4-(dimethoxymethyl)phenyl]pent-2-en-4-yn-1-ol 在 四(三苯基膦)钯 吗啉 、 氢氧化钾 、 potassium azodicarboxylate 、 碘 、 溶剂黄146 、 silver carbonate 作用下， 以 四氢呋喃 、 苯 为溶剂， 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
• 作为产物：
  描述：

  1-[(E)-3-(tert-Butyl-diphenyl-silanyloxy)-1-trimethylsilanylethynyl-propenyl]-4-dimethoxymethyl-benzene 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 生成 (Z)-3-[4-(dimethoxymethyl)phenyl]pent-2-en-4-yn-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.