N-benzyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexan-1-imine | 1452424-19-9

• 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: N-benzyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexan-1-imine
• CAS: 1452424-19-9
• 化学式: C₁₉H₃₀BNO₂
• 分子量: 315.264
• InChiKey: QKDFQTYECYJTIN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.91
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  30.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-benzyl-4-(n-propyl)-1-azabuta-1,3-diene 、 联硼酸频那醇酯 在 三苯基膦 、 copper(l) chloride 、 sodium t-butanolate 作用下， 以 甲醇 为溶剂， 反应 6.0h， 生成 N-benzyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexan-1-imine
  参考文献：
  名称：

  A Selective Transformation of Enals into Chiral γ-Amino Alcohols

  摘要：

  A one-pot synthesis of chiral amino alcohols from alpha,beta-unsaturated aldehydes is reported which circumvents competitive 1,2-versus 1,4-boryl addition, by means of using a sterically hindered amine-derived imine. In addition to the complete chemoselectivity, modification of the Cu(I) catalyst with readily available chiral diphosphines, such as (R)-DM-BINAP, gave the 1,4-boryl addition products with high levels of asymmetric induction.

  DOI：

  10.1021/ol4022029

文献信息

• A Selective Transformation of Enals into Chiral γ-Amino Alcohols
  作者：Adam D. J. Calow、Andrei S. Batsanov、Alba Pujol、Cristina Solé、Elena Fernández、Andrew Whiting

  DOI：10.1021/ol4022029

  日期：2013.9.20

  A one-pot synthesis of chiral amino alcohols from alpha,beta-unsaturated aldehydes is reported which circumvents competitive 1,2-versus 1,4-boryl addition, by means of using a sterically hindered amine-derived imine. In addition to the complete chemoselectivity, modification of the Cu(I) catalyst with readily available chiral diphosphines, such as (R)-DM-BINAP, gave the 1,4-boryl addition products with high levels of asymmetric induction.