2-(buta-2,3-dien-2-yl)-4,4,5,5-tetraphenyl-1,3,2-dioxaborolane | 1191381-42-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 2-(buta-2,3-dien-2-yl)-4,4,5,5-tetraphenyl-1,3,2-dioxaborolane
• 英文别名: 2-Buta-2,3-dien-2-yl-4,4,5,5-tetraphenyl-1,3,2-dioxaborolane
• CAS: 1191381-42-6
• 化学式: C₃₀H₂₅BO₂
• 分子量: 428.338
• InChiKey: JCYZCYQUNJTAID-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.68
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  反式肉桂醛 、 2-(buta-2,3-dien-2-yl)-4,4,5,5-tetraphenyl-1,3,2-dioxaborolane 在 双氧水 、 sodium hydroxide 作用下， 以 甲苯 为溶剂， 反应 6.0h， 以75%的产率得到(3R,4R,E)-4-methyl-1-phenylhexa-1,5-diene-3,4-diol
  参考文献：
  名称：

  Enantioselective Synthesis of 2-Methyl-1,2-syn- and 2-Methyl-1,2-anti-3-butenediols via Allene Hydroboration−Aldehyde Allylboration Reaction Sequences

  摘要：

  The hydroboration of allene 7 with ((d)lpc)(z)BH at 0 degrees C provides the kinetic allylborane 12Z with >20:1 selectivity. However, when the hydroboration is performed at 85 degrees C, the kinetically formed allylborane isomerizes to give the thermodynamic allylborane 12E with >= 12:1 selectivity. Subsequent treatment of 12Z or 12E with aldehydes at -78 degrees C, followed by oxidative workup, provides the 2-methyl-1,2-diols 8 and 9 in good yield and with 80-92% e.e.

  DOI：

  10.1021/ja904599h
• 作为产物：
  描述：

  2-isopropoxy-4,4,5,5-tetraphenyl-1,3,2-dioxaborolane 、 1-溴-2-丁炔 在 magnesium 、 mercury dichloride 作用下， 以 乙醚 为溶剂， 以835 mg的产率得到2-(buta-2,3-dien-2-yl)-4,4,5,5-tetraphenyl-1,3,2-dioxaborolane
  参考文献：
  名称：

  Enantioselective Synthesis of 2-Methyl-1,2-syn- and 2-Methyl-1,2-anti-3-butenediols via Allene Hydroboration−Aldehyde Allylboration Reaction Sequences

  摘要：

  The hydroboration of allene 7 with ((d)lpc)(z)BH at 0 degrees C provides the kinetic allylborane 12Z with >20:1 selectivity. However, when the hydroboration is performed at 85 degrees C, the kinetically formed allylborane isomerizes to give the thermodynamic allylborane 12E with >= 12:1 selectivity. Subsequent treatment of 12Z or 12E with aldehydes at -78 degrees C, followed by oxidative workup, provides the 2-methyl-1,2-diols 8 and 9 in good yield and with 80-92% e.e.

  DOI：

  10.1021/ja904599h

文献信息

• Enantioselective Synthesis of 2-Methyl-1,2-<i>syn</i>- and 2-Methyl-1,2-<i>anti</i>-3-butenediols via Allene Hydroboration−Aldehyde Allylboration Reaction Sequences
  作者：Ming Chen、Masaki Handa、William R. Roush

  DOI：10.1021/ja904599h

  日期：2009.10.21

  The hydroboration of allene 7 with ((d)lpc)(z)BH at 0 degrees C provides the kinetic allylborane 12Z with >20:1 selectivity. However, when the hydroboration is performed at 85 degrees C, the kinetically formed allylborane isomerizes to give the thermodynamic allylborane 12E with >= 12:1 selectivity. Subsequent treatment of 12Z or 12E with aldehydes at -78 degrees C, followed by oxidative workup, provides the 2-methyl-1,2-diols 8 and 9 in good yield and with 80-92% e.e.