(9Z)-11-methylretinal | 135414-23-2

• 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: (9Z)-11-methylretinal
• 英文别名: (2E,4E,6Z,8E)-3,5,7-trimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenal
• CAS: 135414-23-2
• 化学式: C₂₁H₃₀O
• 分子量: 298.469
• InChiKey: RRNMAWQHIDHHNP-ZXDLZHIOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.48
• 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：

  (9Z)-11-methylretinal 在 碘 作用下， 生成 all-trans-11-methylretinal
  参考文献：
  名称：

  Efficient preparation of 9-Z-11-methylretinal and 11-Z-11-methylretinal

  摘要：

  [2-(beta-Ionylidene)propyl]triphenylphosphonium bromide is reacted with 3-methyl-4-oxobut-2-enenitrile in refluxing 1,2-epoxybutane to give a mixture of 11-Z- and all-E-11-methylretinal via DIBAL-H reduction. In an analogous fashion, beta-ionyl triphenylphosphonium bromide is reacted with 3,5-dimethyl-6-oxohexa-2,4-dienenitrile in 1,2-epoxybutane followed by subsequent DIBAL-H reduction to afford a mixture of new products consisting of 9-Z-11-methylretinal, its all-E isomer and 1-(2',6',6'-trimethylcyclohex-2'-en-1'-yl)-6-(buten-2 ''-al-3 ''-yl)-3,5-dimethylcyclohexa-1,3-diene. These molecules were obtained in pure form by HPLC. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.11.144
• 作为产物：
  描述：

  3,5-dimethyl-6-oxohexa-2,4-dienenitrile 、 β-Ionyl-triphenylphosphoniumhydroxyd 在 1,2-环氧丁烷 、 二异丁基氢化铝 、 水 、 silica gel 作用下， 以 Petroleum ether 为溶剂， 反应 63.5h， 以39%的产率得到
  参考文献：
  名称：

  Efficient preparation of 9-Z-11-methylretinal and 11-Z-11-methylretinal

  摘要：

  [2-(beta-Ionylidene)propyl]triphenylphosphonium bromide is reacted with 3-methyl-4-oxobut-2-enenitrile in refluxing 1,2-epoxybutane to give a mixture of 11-Z- and all-E-11-methylretinal via DIBAL-H reduction. In an analogous fashion, beta-ionyl triphenylphosphonium bromide is reacted with 3,5-dimethyl-6-oxohexa-2,4-dienenitrile in 1,2-epoxybutane followed by subsequent DIBAL-H reduction to afford a mixture of new products consisting of 9-Z-11-methylretinal, its all-E isomer and 1-(2',6',6'-trimethylcyclohex-2'-en-1'-yl)-6-(buten-2 ''-al-3 ''-yl)-3,5-dimethylcyclohexa-1,3-diene. These molecules were obtained in pure form by HPLC. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.11.144

文献信息

• Efficient preparation of 9-Z-11-methylretinal and 11-Z-11-methylretinal
  作者：Prativa B.S. Dawadi、Michiel A. Verhoeven、Johan Lugtenburg

  DOI：10.1016/j.tetlet.2010.11.144

  日期：2011.2

  [2-(beta-Ionylidene)propyl]triphenylphosphonium bromide is reacted with 3-methyl-4-oxobut-2-enenitrile in refluxing 1,2-epoxybutane to give a mixture of 11-Z- and all-E-11-methylretinal via DIBAL-H reduction. In an analogous fashion, beta-ionyl triphenylphosphonium bromide is reacted with 3,5-dimethyl-6-oxohexa-2,4-dienenitrile in 1,2-epoxybutane followed by subsequent DIBAL-H reduction to afford a mixture of new products consisting of 9-Z-11-methylretinal, its all-E isomer and 1-(2',6',6'-trimethylcyclohex-2'-en-1'-yl)-6-(buten-2 ''-al-3 ''-yl)-3,5-dimethylcyclohexa-1,3-diene. These molecules were obtained in pure form by HPLC. (C) 2010 Elsevier Ltd. All rights reserved.