3-m-tolyl-3H-benzofuran-2-one | 65425-04-9

• 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: 3-m-tolyl-3H-benzofuran-2-one
• 英文别名: 3-m-Tolyl-3H-benzofuran-2-on；3-(3-methylphenyl)-3H-1-benzofuran-2-one
• CAS: 65425-04-9
• 化学式: C₁₅H₁₂O₂
• 分子量: 224.259
• InChiKey: PCPINHMOCAOUDF-UHFFFAOYSA-N

物化性质

• 沸点：
  327.4±37.0 °C(Predicted)
• 密度：
  1.202±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 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：

  3-m-tolyl-3H-benzofuran-2-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-(2-oxo-3-(m-tolyl)-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
• 作为产物：
  描述：

  3-甲基扁桃酸 、 苯酚 在 硫酸 作用下， 生成 3-m-tolyl-3H-benzofuran-2-one
  参考文献：
  名称：

  Antispasmodics. Derivatives of 3-Phenyl-2-benzofuranone¹

  摘要：

  DOI：

  10.1021/ja01123a021

文献信息

• Chiral Calcium Phosphate Catalyzed Enantioselective Amination of 3-Aryl-2-benzofuranones
  作者：Ruihan Liu、Suvratha Krishnamurthy、Zhenwei Wu、K. S. Satyanarayana Tummalapalli、Jon C. Antilla

  DOI：10.1021/acs.orglett.0c03059

  日期：2020.10.16

  4-tert-butyl-phenyl substituted (R)-[H8]-BINOL chiral calcium phosphate catalyzed enantioselective amination of 3-aryl-2-benzofuranones with dibenzyl azodicarboxylate is described. The catalyst loading of the reaction is 1 mol %. This transformation is facile and has a high degree atom economy, which gave products with good yields and high enantioselectivities (79% to 99%). This reaction has excellent ee

  描述了4-叔丁基-苯基取代的（R）-[H 8 ] -BINOL手性磷酸钙催化的3-芳基-2-苯并呋喃酮与偶氮二羧酸二苄酯的对映选择性胺化。反应的催化剂负载量是1mol％。这种转变是容易的，并且具有高度的原子经济性，这使得产物具有良好的产率和高对映选择性（79％至99％）。该反应具有优异的ee和较宽的底物范围以及温和的反应条件。
• 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...
• Catalytic Desymmetrization of <i>meso</i>-Aziridines with Benzofuran-2(3<i>H</i>)-Ones Employing a Simple In Situ-Generated Magnesium Catalyst
  作者：Dan Li、Linqing Wang、Dongxu Yang、Bangzhi Zhang、Rui Wang

  DOI：10.1021/acscatal.5b02177

  日期：2015.12.4

  The first example of catalytic desymmetrization of meso-aziridines with benzofuran-2(3H) -ones is realized by employing a magnesium catalyst utilizing BINOL as a simple and commercially available chiral ligand. Both of the enantiomers of the ring-opening product could be easily accessed by employing (R)- or (S)-BINOL as chiral ligand, respectively. A variety of enantioenriched 3,3disubstituted benzofuran-2(3H)-ones containing multiple linear continuous stereocenters were obtained with moderate to good yields, diastereo- and enantioselectivities.
• [EN] STABILIZED POLYOLEFIN COMPOSITIONS COMPRISING BENZOFURANONES AND HINDERED PHENOLIC ANTIOXIDANTS<br/>[FR] COMPOSITIONS DE POLYOLÉFINES STABILISÉES COMPRENANT DES BENZOFURANONES ET DES ANTIOXYDANTS À ENCOMBREMENT PHÉNOLIQUE
  申请人：BASF SE

  公开号：WO2019010167A1

  公开（公告）日：2019-01-10

  Polyolefin compositions comprising i) a polyolefin, ii) one or more phosphorus- containing benzofuranone compounds and iii) one or more hindered phenolic antioxidants are provided excellent protection against discoloration and enhanced thermal stability during melt processing as exhibited by improved retention of molecular weight and maintenance of polymer molecular architecture.
• [EN] STABILIZED POLYOLEFIN COMPOSITIONS COMPRISING BENZOFURANONES AND HINDERED AMINE LIGHT STABILIZERS<br/>[FR] COMPOSITIONS DE POLYOLÉFINES STABILISÉES COMPRENANT DES BENZOFURANONES ET DES PHOTOSTABILISANTS À AMINE ENCOMBRÉE
  申请人：BASF SE

  公开号：WO2019010176A1

  公开（公告）日：2019-01-10

  Polyolefin compositions comprising i) a polyolefin, ii) one or more phosphorus- containing benzofuranone compounds and iii) one or more hindered amine light stabilizers are provided excellent protection against discoloration and enhanced thermal stability during melt processing as exhibited by improved retention of molecular weight and maintenance of polymer molecular architecture.