(S)-3-(3-methoxyphenyl)isobenzofuran-1(3H)-one | 1613406-82-8

• 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: (S)-3-(3-methoxyphenyl)isobenzofuran-1(3H)-one
• CAS: 1613406-82-8
• 化学式: C₁₅H₁₂O₃
• 分子量: 240.258
• InChiKey: XJDTUIARSAKHJW-AWEZNQCLSA-N

物化性质

• 熔点：
  106-108 °C
• 沸点：
  402.2±45.0 °C(predicted)
• 密度：
  1.236±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.96
• 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：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  2-(3-methoxylbenzoyl)benzaldehyde 在 indium 、 cobalt(II) bromide 、 (-)-1,2-双((2R,5R)-2,5-二苯基膦)乙烷 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以87%的产率得到
  参考文献：
  名称：

  Cobalt-Catalyzed Enantioselective Intramolecular Hydroacylation of Ketones and Olefins

  摘要：

  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.

  DOI：

  10.1021/ja509919x

文献信息

• 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。
• 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.