1-(3-bromophenyl)allyl benzoate | 1234617-98-1

• 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: 1-(3-bromophenyl)allyl benzoate
• 英文别名: 1-(3-Bromophenyl)prop-2-enyl benzoate
• CAS: 1234617-98-1
• 化学式: C₁₆H₁₃BrO₂
• 分子量: 317.182
• InChiKey: QYSCPLWOKRWMEG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(3-bromophenyl)allyl benzoate 、 sodium phenoxide 在 C₄₈H₅₀IrNO₄P 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 以95%的产率得到(S)-1-bromo-3-(1-phenoxyallyl)benzene
  参考文献：
  名称：

  Iridium-Catalyzed Kinetic Asymmetric Transformations of Racemic Allylic Benzoates

  摘要：

  Versatile methods for iridium-catalyzed, kinetic asymmetric substitution of racemic, branched allylic esters are reported. These reactions occur with a variety of aliphatic, aryl, and heteroaryl allylic benzoates to form the corresponding allylic substitution products in high yields (74-96%) with good to excellent enantioselectivity (84-98% ee) with a scope that encompasses a range of anionic carbon and heteroatom nucleophiles. These kinetic asymmetric processes occur with distinct stereochemical courses for racemic aliphatic and aromatic allylic benzoates, and the high reactivity of branched allylic benzoates enables enantioselective allylic substitutions that are slow or poorly selective with linear allylic electrophiles.

  DOI：

  10.1021/ja103779e
• 作为产物：
  描述：

  间溴苯甲醛 、 乙烯基氯化镁 、 苯甲酰氯 在 吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以80%的产率得到1-(3-bromophenyl)allyl benzoate
  参考文献：
  名称：

  Iridium-Catalyzed Kinetic Asymmetric Transformations of Racemic Allylic Benzoates

  摘要：

  Versatile methods for iridium-catalyzed, kinetic asymmetric substitution of racemic, branched allylic esters are reported. These reactions occur with a variety of aliphatic, aryl, and heteroaryl allylic benzoates to form the corresponding allylic substitution products in high yields (74-96%) with good to excellent enantioselectivity (84-98% ee) with a scope that encompasses a range of anionic carbon and heteroatom nucleophiles. These kinetic asymmetric processes occur with distinct stereochemical courses for racemic aliphatic and aromatic allylic benzoates, and the high reactivity of branched allylic benzoates enables enantioselective allylic substitutions that are slow or poorly selective with linear allylic electrophiles.

  DOI：

  10.1021/ja103779e

文献信息

• Iridium-Catalyzed Kinetic Asymmetric Transformations of Racemic Allylic Benzoates
  作者：Levi M. Stanley、Chen Bai、Mitsuhiro Ueda、John F. Hartwig

  DOI：10.1021/ja103779e

  日期：2010.7.7

  Versatile methods for iridium-catalyzed, kinetic asymmetric substitution of racemic, branched allylic esters are reported. These reactions occur with a variety of aliphatic, aryl, and heteroaryl allylic benzoates to form the corresponding allylic substitution products in high yields (74-96%) with good to excellent enantioselectivity (84-98% ee) with a scope that encompasses a range of anionic carbon and heteroatom nucleophiles. These kinetic asymmetric processes occur with distinct stereochemical courses for racemic aliphatic and aromatic allylic benzoates, and the high reactivity of branched allylic benzoates enables enantioselective allylic substitutions that are slow or poorly selective with linear allylic electrophiles.