(1R,2R,E)-2-methyl-1-phenylpent-3-ene-1,2-diol | 1380240-23-2

• 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: (1R,2R,E)-2-methyl-1-phenylpent-3-ene-1,2-diol
• 英文别名: (E,1R,2R)-2-methyl-1-phenylpent-3-ene-1,2-diol
• CAS: 1380240-23-2
• 化学式: C₁₂H₁₆O₂
• 分子量: 192.258
• InChiKey: LRVUCFKLRHZOBB-UHTQEIBISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.05
• 重原子数：
  14.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  (1R,2R,E)-2-methyl-1-phenylpent-3-ene-1,2-diol 、 甲氧基-三氟甲基苯 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：

  4,4,5,5-tetramethyl-2-(penta-2,3-dien-2-yl)-1,3,2-dioxaborolane 在 双氧水 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 反应 21.0h， 生成 (1R,2R,E)-2-methyl-1-phenylpent-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

文献信息

• Zn/InCl₃-Mediated Pinacol Cross-Coupling Reactions of Aldehydes with α,β-Unsaturated Ketones in Aqueous Media
  作者：Yong-Sheng Yang、Zhi-Liang Shen、Teck-Peng Loh

  DOI：10.1021/ol900619d

  日期：2009.5.21

  A zinc/indium chloride-mediated pinacol cross-coupling reaction between aldehyde and alpha,beta-unsaturated ketone in aqueous media was developed. The 1,2-diols were obtained in moderate to good yields with up to 93:7 diastereoselectivity.