6-bromo-3-phenylbenzofuran-2(3H)-one | 1284257-28-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 香豆素
• 英文名称: 6-bromo-3-phenylbenzofuran-2(3H)-one
• 英文别名: 6-bromo-3-phenyl-3H-1-benzofuran-2-one
• CAS: 1284257-28-8
• 化学式: C₁₄H₉BrO₂
• 分子量: 289.128
• InChiKey: HJUTVFJQHFMVEC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 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：

  6-bromo-3-phenylbenzofuran-2(3H)-one 、 2-重氮基-2-苯基乙酸叔丁酯酯 在 di-μ-chlorobis(norbornadiene)dirhodium(I) 、 potassium carbonate 作用下， 以 甲苯 为溶剂， 反应 3.0h， 生成 tert-butyl 2-(6-bromo-2-oxo-3-phenyl-2,3-dihydrobenzofuran-3-yl)-2-phenylacetate
  参考文献：
  名称：

  Asymmetric Rh(I)-Catalyzed Functionalization of the 3-C(sp³)–H Bond of Benzofuranones with α-Diazoesters

  摘要：

  An asymmetric Rh(I)-catalyzed functionalization of the 3-C(sp(3))-H bond of benzofuranones with alpha-diazoesters has been developed, providing a new strategy for the stereoselective 3-alkylation of benzofuranones. With low catalyst loadings (low to 0.02 mol % Rh), a number of benzofuranones bearing consecutive quaternary and tertiary stereogenic centers have been synthesized (up to 94% yield, 95:5 dr, and >99% ee). The synthetic utilities of this methodology have been demonstrated by elaborating the model product 3aa to a series of enantiopure compounds with similarities to natural products and drug candidates.

  DOI：

  10.1021/acs.orglett.8b02555

文献信息

• Organocatalytic Asymmetric Branching Sequence of MBH Carbonates: Access to Chiral Benzofuran-2(3<i>H</i>)-one Derivatives with Three Stereocenters
  作者：Chuanle Zhu、Lijun Yang、Jing Nie、Yan Zheng、Junan Ma

  DOI：10.1002/cjoc.201200809

  日期：2012.11

  An organocatalytic asymmetric branching sequence was realized in the presence of 10 mol% of (DHQD)2AQN, affording the sequential products with three stereocentres, including two quaternary carbon centres, in 47%–79% yields with 85%–99% ee.

  在10摩尔％（DHQD）2 AQN的存在下实现了有机催化不对称分支序列，提供了具有三个立体中心（包括两个季碳中心）的顺序产物，产率为47％-79％，ee为85％-99％。