(1S,2R,E)-1-cyclohexyl-2-methylpent-3-ene-1,2-diol | 1380240-30-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2R,E)-1-cyclohexyl-2-methylpent-3-ene-1,2-diol
• 英文别名: (E,1S,2R)-1-cyclohexyl-2-methylpent-3-ene-1,2-diol
• CAS: 1380240-30-1
• 化学式: C₁₂H₂₂O₂
• 分子量: 198.305
• InChiKey: UNWIHEOURYIKNS-XLFQXWAYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1S,2R,E)-1-cyclohexyl-2-methylpent-3-ene-1,2-diol 、 (R)-methoxytrifluoromethylphenylacetyl chloride 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Diastereo- and Enantioselective Synthesis of (E)-2-Methyl-1,2-syn- and (E)-2-Methyl-1,2-anti-3-pentenediols via Allenylboronate Kinetic Resolution with (^dIpc)₂BH and Aldehyde Allylboration

  摘要：

  Enantioselective hydroboration of racemic allenylboronate (+/-)-1 with 0.48 equiv of ((d)Ipc)(2)BH at -25 degrees C proceeds with efficient kinetic resolution and provides allylborane (R)-Z-4. When heated to 95 degrees C, allylborane (R)-Z-4 isomerizes to the thermodynamically more stable allylborane isomer (S)-E-7. Subsequent allylboration of aldehydes with (R)-Z-4 or (S)-E-7 at -78 degrees C followed by oxidative workup provides 1,2-syn- or 1,2-anti-diols, 2 or 3, respectively, in 87-94% ee.

  DOI：

  10.1021/ol3010968
• 作为产物：
  描述：

  在 双氧水 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 反应 12.0h， 生成 (E)-1-cyclohexyl-2-methylpent-3-ene-1,2-diol 、 (1S,2R,E)-1-cyclohexyl-2-methylpent-3-ene-1,2-diol
  参考文献：
  名称：

  Diastereo- and Enantioselective Synthesis of (E)-2-Methyl-1,2-syn- and (E)-2-Methyl-1,2-anti-3-pentenediols via Allenylboronate Kinetic Resolution with (^dIpc)₂BH and Aldehyde Allylboration

  摘要：

  Enantioselective hydroboration of racemic allenylboronate (+/-)-1 with 0.48 equiv of ((d)Ipc)(2)BH at -25 degrees C proceeds with efficient kinetic resolution and provides allylborane (R)-Z-4. When heated to 95 degrees C, allylborane (R)-Z-4 isomerizes to the thermodynamically more stable allylborane isomer (S)-E-7. Subsequent allylboration of aldehydes with (R)-Z-4 or (S)-E-7 at -78 degrees C followed by oxidative workup provides 1,2-syn- or 1,2-anti-diols, 2 or 3, respectively, in 87-94% ee.

  DOI：

  10.1021/ol3010968