(3S,6R,7S,E)-4,6-dimethyl-1,9-diphenylnon-4-ene-3,7-diol | 1380240-37-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3S,6R,7S,E)-4,6-dimethyl-1,9-diphenylnon-4-ene-3,7-diol
• CAS: 1380240-37-8
• 化学式: C₂₃H₃₀O₂
• 分子量: 338.49
• InChiKey: VHUCBZSLCULULS-RADWGGJRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.56
• 重原子数：
  25.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  40.46
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (3S,6R,7S,E)-4,6-dimethyl-1,9-diphenylnon-4-ene-3,7-diol 在 臭氧 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 生成 (4S,5R)-2,2,5-trimethyl-4-phenethyl-1,3-dioxane
  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：

  苯丙醛 、 4,4,5,5-tetramethyl-2-(penta-2,3-dien-2-yl)-1,3,2-dioxaborolane 、 diisopinocampheylborane 以 甲苯 为溶剂， 反应 6.5h， 生成 (3S,4S)-4-methyl-1-phenylhept-5-yn-3-ol 、 (3R,4S)-4-methyl-1-phenylhept-5-yn-3-ol 、 (3S,4R)-4-methyl-1-phenylhept-5-yn-3-ol 、 (3R,4R)-4-methyl-1-phenylhept-5-yn-3-ol 、 4,6-dimethyl-1,9-diphenylnon-4-ene-3,7-diol 、 (Z)-4,6-dimethyl-1,9-diphenylnon-4-ene-3,7-diol 、 (3S,6R,7S,E)-4,6-dimethyl-1,9-diphenylnon-4-ene-3,7-diol 、 (3R,6S,7R,E)-4,6-dimethyl-1,9-diphenylnon-4-ene-3,7-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