3-[(4-chlorophenyl)methyl]-3H-1-benzofuran-2-one | 1433450-11-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 3-[(4-chlorophenyl)methyl]-3H-1-benzofuran-2-one
• CAS: 1433450-11-3
• 化学式: C₁₅H₁₁ClO₂
• 分子量: 258.704
• InChiKey: DHDVNKCHKYCSOL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.59
• 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：

  methyl 2-phthalimidoacrylate 、 3-[(4-chlorophenyl)methyl]-3H-1-benzofuran-2-one 在 1-(3,5-bis(trifluoromethyl)benzyl)-3-((1S,2S)-2-(dimethylamino)cyclohexyl)thiourea 作用下， 以 氯苯 为溶剂， 反应 120.0h， 以98%的产率得到(S)-methyl 3-((S)-3-(4-chlorobenzyl)-2-oxo-2,3-dihydrobenzofuran-3-yl)-2-(1,3-dioxoisoindolin-2-yl)propanoate
  参考文献：
  名称：

  苯并呋喃-2-酮与2-邻苯二甲酰亚胺基丙烯酸烷基酯的不对称共轭加成：模拟结构-立体选择性与立体和电子参数的关系

  摘要：

  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。

  DOI：

  10.1002/anie.201601028

文献信息

• 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 addition of 3-substituted benzofuran-2-ones to isatin N-Boc ketimines catalyzed by chiral biscinchona alkaloid catalyst
  作者：Yi Zhu、Enge Zhang、Chao Luo、Xin Li、Jin-Pei Cheng

  DOI：10.1016/j.tet.2015.04.114

  日期：2015.6

  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.
• 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.