(R)-3-(3-methoxyphenyl)isobenzofuran-1(3H)-one | 1613406-83-9

• 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: (R)-3-(3-methoxyphenyl)isobenzofuran-1(3H)-one
• 英文别名: 3-(3-methoxyphenyl)isobenzofuran-1(3H)-one；(3R)-3-(3-methoxyphenyl)-3H-2-benzofuran-1-one
• CAS: 1613406-83-9
• 化学式: C₁₅H₁₂O₃
• 分子量: 240.258
• InChiKey: XJDTUIARSAKHJW-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-醛基苯甲酸甲酯 、 3-甲氧基苯硼酸 在 diethylzinc 、 (R_a)-2'-(((S)-2-(hydroxydiphenylmethyl)pyrrolidin-1-yl)methyl)-3-(trifluoromethyl)-[1,1'-binaphthalen]-2-ol 作用下， 以 甲苯 为溶剂， 反应 48.5h， 以90%的产率得到
  参考文献：
  名称：

  联萘-脯氨醇手性配体：设计及其在芳香醛对映选择性芳基化中的应用

  摘要：

  联萘-脯氨醇配体被设计并应用于芳香醛的对映选择性芳基化和2-甲酰基苯甲酸甲酯的顺序芳基化-内酯化。在优化的条件下，反应分别以高达 96% 的产率和高达 99% 的 ee 和高达 89% 的产率和高达 99% 的 ee 提供了所需的二芳基甲醇和 3-芳基苯酞。特别是，通过重结晶大量获得了基本上光学纯的 3-芳基苯酞（超过 99% ee）。

  DOI：

  10.1039/d1ob00289a

文献信息

• Rhodium(III)-Catalyzed Asymmetric Addition of Inert Arene C–H Bond to Aldehydes To Afford Enantioenriched Phthalides
  作者：Wenkun Chen、Jie Li、Hui Xie、Jun Wang

  DOI：10.1021/acs.orglett.0c01052

  日期：2020.5.1

  An asymmetric rhodium(III)-catalyzed Grignard-type addition of inert arene C-H bond to aldehydes is reported. It provides a new strategy for the synthesis of chiral 3-substituted phthalides in good yields (up to 87%) with high enantiomeric purity (up to 99% ee). Interestingly, a chiral-matching effect between substrate and catalyst was observed, which is crucial to accomplish satisfied reaction outcomes

  据报道，惰性芳烃CH键不对称地由铑（III）催化的格氏（Grignard）型加成到醛上。它为高收率（最高99％ee）的高收率（最高87％）的手性3-取代邻苯二甲酸酯的合成提供了新的策略。有趣的是，观察到底物与催化剂之间的手性匹配效应，这对于完成满意的反应结果至关重要。从机理上讲，假定该反应通过苯甲酰胺的连续C（sp2）-H活化，加成醛和内酯化而进行。
• Catalytic asymmetric synthesis of 3-aryl phthalides enabled by arylation–lactonization of 2-formylbenzoates
  作者：Andressa M. M. Carlos、Rafael Stieler、Diogo S. Lüdtke

  DOI：10.1039/c8ob02872a

  日期：——

  The catalytic asymmetric synthesis of 3-aryl phthalides is reported through a sequential asymmetric arylation–lactonization reaction. The reaction is enabled by a boron–zinc exchange to generate reactive arylating agents, which react with 2-formylbenzoates in the presence of a chiral amino naphthol ligand. The enantiodetermining step is the arylation of the aldehyde, which then undergoes a lactonization

  据报道，通过顺序的不对称芳基化-内酯化反应可以催化3-芳基邻苯二甲酸酯的不对称合成。硼锌交换使该反应产生反应性芳基化剂，在手性氨基萘酚配体存在下与2-甲酰基苯甲酸酯反应。对映体确定步骤是醛的芳基化，然后进行内酯化反应，以良好的收率和对映选择性产生相应的邻苯二甲酸酯。
• Catalytic asymmetric 1,2-Addition/Lactonization tandem reactions for the syntheses of chiral 3-Substituted phthalides using organozinc reagents
  作者：Huayin Huang、Yabai Wang、Hua Zong、Ling Song

  DOI：10.1002/aoc.4643

  日期：2019.1

  Using chiral phosphoramide ligand 2d‐Zn (II) complex derived from (1R,2R)‐1,2‐diphenylethylenediamine as the catalyst, we have developed efficient catalytic asymmetric 1,2‐addition/lactonization tandem reactions of diverse organozinc reagents with varied methyl 2‐formylbenzoates for the construction of optically enriched 3‐aryl or alkyl substituted phthalides, which are significant building blocks

  使用衍生自（1 R，2 R）-1,2-二苯基乙二胺的手性磷酰胺配体2d- Zn（II）络合物作为催化剂，我们开发了各种有机锌试剂与以下化合物的有效催化不对称1,2-加成/内酯串联反应。各种2-甲酰基苯甲酸甲酯用于构建光学富集的3-芳基或烷基取代的邻苯二甲酸酯，这是许多重要的手性药物和天然产物的重要组成部分。可以提供具有良好至优异产率（高达95％）和中等至良好对映选择性（高达89％）的相应产物。
• Cobalt-Catalyzed Enantioselective Intramolecular Hydroacylation of Ketones and Olefins
  作者：Junfeng Yang、Naohiko Yoshikai

  DOI：10.1021/ja509919x

  日期：2014.12.3

  Cobalt-chiral diphoshine catalytic systems promote intramolecular hydroacylation reactions of 2-acylbenzaldehydes and 2-alkenylbenzaldehydes to afford phthalide and indanone derivatives, respectively, in moderate to good yields with high enantioselectivities. The ketone hydroacylation did not exhibit a significant H/D kinetic isotope effect (KIE) with respect to the aldehyde C-H bond, indicating that C-H activation would not be involved in the rate-limiting step.
• Diastereomeric Aziridine Carbinol Catalyzed Enantioselective Arylation Reaction: Toward the Asymmetric Synthesis of Both Enantiomers of Chiral 3-Aryl Phthalide
  作者：Xixi Song、Yuan-Zhao Hua、Jing-Guo Shi、Ping-Ping Sun、Min-Can Wang、Junbiao Chang

  DOI：10.1021/jo500796w

  日期：2014.7.3

  The diastereomeric aziridine carbinols are applied, respectively, as efficient chiral ligand in the catalysis of asymmetric arylation and sequential arylation-lactonization cascade. The two diastereomers, which are facilely synthesized from the same chiral source, function as pseudo enantiomers in arylation of aromatic aldehydes providing the different enantiomers of the diarylmethanols with almost the same excellent enantioselectivities. The arylation method is also carried out in tandem with lactonization process to afford a concise synthetic approach to both enantiomers of optically active 3-aryl phthalide.