3-[(3-bromophenyl)methyl]-3H-1-benzofuran-2-one | 1433450-25-9

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 3-[(3-bromophenyl)methyl]-3H-1-benzofuran-2-one
• CAS: 1433450-25-9
• 化学式: C₁₅H₁₁BrO₂
• 分子量: 303.155
• InChiKey: JQLFZSLRIGCFBN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.69
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  tert-butyl (1-benzyl-2-oxoindolin-3-ylidene)carbamate 、 3-[(3-bromophenyl)methyl]-3H-1-benzofuran-2-one 在 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 作用下， 以 甲基叔丁基醚 为溶剂， 反应 72.0h， 以97%的产率得到tert-butyl ((R)-1-benzyl-3-((R)-3-(3-bromobenzyl)-2-oxo-2,3-dihydrobenzofuran-3-yl)-2-oxoindolin-3-yl)carbamate
  参考文献：
  名称：

  Asymmetric addition of 3-substituted benzofuran-2-ones to isatin N-Boc ketimines catalyzed by chiral biscinchona alkaloid catalyst

  摘要：

  A highly enantioselective Mannich reaction of 3-substituted benzofuran-2(3H)-ones and isatin N-Boc ketimines catalyzed by a chiral biscinchona alkaloid catalyst was developed, which proved to be an efficient way for the synthesis of chiral 3,3'-disubstituted benzofuran-2-one derivatives. The nucleophilic addition products were generally obtained in high yields (up to 99%) with very good diastereoselectivities (up to >95:5 dr) and enantioselectivities (up to 98% ee). (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.04.114

文献信息

• Asymmetric Conjugate Addition of Benzofuran-2-ones to Alkyl 2-Phthalimidoacrylates: Modeling Structure-Stereoselectivity Relationships with Steric and Electronic Parameters
  作者：Chen Yang、En-Ge Zhang、Xin Li、Jin-Pei Cheng

  DOI：10.1002/anie.201601028

  日期：2016.5.23

  A highly predictive model to correlate the steric and electronic parameters of tertiary amine thiourea catalysts with the stereoselectivity of Michael reactions of 3‐substituted benzofuranones and alkyl 2‐phthalimidoacrylates is described. As predicted, new 3,5‐bis(trifluoromethyl)benzyl‐ and methyl‐substituted tertiary amine thioureas turned out to be highly suitable catalysts for this reaction and

  描述了一个高度预测性的模型，该模型将叔胺硫脲催化剂的空间和电子参数与3-取代的苯并呋喃酮和2-邻苯二甲酰亚胺基丙烯酸烷基酯的迈克尔反应的立体选择性相关。如预料的那样，新的3,5-双（三氟甲基）苄基和甲基取代的叔胺硫脲被证明是非常适合该反应的催化剂，并能够合成具有1,3-不相邻的立体中心的对映体富集的α-氨基酸衍生物。
• Organocatalytic asymmetric formal arylation of benzofuran-2(3H)-ones with cooperative visible light photocatalysis
  作者：Yang Liu、Jiangtao Li、Xinyi Ye、Xiaowei Zhao、Zhiyong Jiang

  DOI：10.1039/c6cc07105h

  日期：——

  An organocatalytic asymmetric reaction of benzofuran-2(3H)-ones with naphthoquinones is disclosed. The current method provides a direct way to furnish arylation of benzofuran-2(3H)-ones in high yields with excellent enantioselectivities. A cooperative...

  公开了苯并呋喃-2（3H）-酮与萘醌的有机催化不对称反应。目前的方法提供了直接的方法，以高产率提供具有优异对映选择性的苯并呋喃-2（3H）-芳基化。合作社...
• P-Spiro phosphonium salts catalyzed asymmetric fluorination of 3-substituted benzofuran-2(3H)-ones
  作者：Chuan-Le Zhu、Xiao-Yun Fu、Ai-Jia Wei、Dominique Cahard、Jun-An Ma

  DOI：10.1016/j.jfluchem.2013.03.007

  日期：2013.6

  Asymmetric electrophilic fluorination of 3-substituted benzofuran-2(3H)-ones was realized under liquid–liquid phase-transfer catalysis with 2 mol% of chiral phosphonium salts to afford the fluorinated products with up to 96% yield and 56% ee.

  的非对称电氟化3-取代的苯并呋喃-2（3 H ^） -酮的混合物在液-液相转移催化实现了与2摩尔％的手性鏻盐，得到氟化产物与高达96％的收率和56％ee的。
• Asymmetric alkylation of 3-substituted benzofuran-2(3H)-ones
  作者：Chao Luo、Enge Zhang、Xin Li

  DOI：10.1016/j.tetlet.2015.09.087

  日期：2015.10

  An enantioselective alkylation reaction of 3-substituted benzofuran-2(3H)-ones catalyzed by a chiral biscinchona alkaloid catalyst combined with TsOH center dot H2O was developed. The corresponding products, containing all carbon quaternary centers at the C3-positions of the benzofuran-2-ones, were obtained in moderate to good yields (up to 89%) with good enantioselectivities (up to 83% ee). (C) 2015 Elsevier Ltd. All rights reserved.