4-bromo-3-(3-methylphenyl)-3,4-dihydroisochromen-1-one | 1354004-88-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 4-bromo-3-(3-methylphenyl)-3,4-dihydroisochromen-1-one
• 英文别名: (3S,4R)-4-bromo-3-(3-methylphenyl)-3,4-dihydroisochromen-1-one
• CAS: 1354004-88-8
• 化学式: C₁₆H₁₃BrO₂
• 分子量: 317.182
• InChiKey: AIOYUPBYSXLTFE-CABCVRRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (E)-2-(3-methylstyryl)benzoic acid 在 N-溴代丁二酰亚胺(NBS) 、 O-[(S)-[(2R,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methyl] N-(2,4-dimethoxyphenyl)carbamothioate 作用下， 以 二氯甲烷 为溶剂， 反应 96.0h， 生成 4-bromo-3-(3-methylphenyl)-3,4-dihydroisochromen-1-one 、
  参考文献：
  名称：

  An Enantioselective Approach toward 3,4-Dihydroisocoumarin through the Bromocyclization of Styrene-type Carboxylic Acids

  摘要：

  A facile and enantioselective approach toward 3,4-dihydroisocoumarin was developed. The method involved an amino-thiocarbamate catalyzed enantioselective bromocyclization of styrene-type carboxylic acids, yielding 3-bromo-3,4-dihydroisocoumarins with good yields and ee's. 3-Bromo-3,4-dihydroisocoumarins are versatile building blocks for various dihydroisocoumarin derivatives in which the Br group can readily be modified to achieve biologically important 4-O-type and 4-N-type 3,4-dihydroisocoumarin systems. In addition, studies indicated that, by refining some parameters, the synthetically useful 5-exo phthalide products could be achieved with good yields and ee's.

  DOI：

  10.1021/jo202221c

文献信息

• Design of Chiral Bifunctional Dialkyl Sulfide Catalysts for Regio‐, Diastereo‐, and Enantioselective Bromolactonization
  作者：Ryuichi Nishiyori、Ayano Tsuchihashi、Ayaka Mochizuki、Kazuma Kaneko、Masahiro Yamanaka、Seiji Shirakawa

  DOI：10.1002/chem.201803703

  日期：2018.11.13

  effective chiral dialkyl sulfide organocatalysts remain relatively rare and under‐developed, despite the potential utility of dialkyl sulfide catalysts. Herein, we report the development of chiral bifunctional dialkyl sulfide catalysts possessing a urea moiety for regio‐, diastereo‐, and enantioselective bromolactonization. The importance of the bifunctional design of chiral sulfide catalysts was clearly

  尽管已经开发出多种用于不对称转化的手性有机催化剂，但是尽管有潜在的实用性，但有效的手性二烷基硫醚有机催化剂仍然相对较少且开发不足。本文中，我们报道了具有脲部分的手性双官能二烷基硫醚催化剂的开发，该脲部分用于区域，非对映和对映选择性溴内酯化。手性硫化物催化剂的双功能设计的重要性在本工作中得到了明确证明。根据实验和理论研究的结果，阐明了催化剂的硫化物和脲部分的作用。
• 5-<i>exo</i>-Selective asymmetric bromolactonization of stilbenecarboxylic acids catalyzed by phenol-bearing chiral thiourea
  作者：Masayuki Sugano、Tsubasa Inokuma、Yousuke Yamaoka、Ken-ichi Yamada

  DOI：10.1039/d3ob01895d

  日期：——

  We developed a novel thiourea Lewis-base catalyst with phenol moieties for the enantioselective 5-exo-bromolactonization of stilbenecarboxylic acids to afford chiral 3-substituted phthalides. The phenol moieties are crucial for the enantio- and regio-selectivity.

  我们开发了一种带有苯酚部分的新型硫脲路易斯碱催化剂，用于二苯乙烯甲酸的对映选择性 5-外型-溴内酯化反应，得到手性 3-取代的苯并呋喃酮。苯酚部分对于对映体和区域选择性至关重要。
• An Enantioselective Approach toward 3,4-Dihydroisocoumarin through the Bromocyclization of Styrene-type Carboxylic Acids
  作者：Jie Chen、Ling Zhou、Chong Kiat Tan、Ying-Yeung Yeung

  DOI：10.1021/jo202221c

  日期：2012.1.20

  A facile and enantioselective approach toward 3,4-dihydroisocoumarin was developed. The method involved an amino-thiocarbamate catalyzed enantioselective bromocyclization of styrene-type carboxylic acids, yielding 3-bromo-3,4-dihydroisocoumarins with good yields and ee's. 3-Bromo-3,4-dihydroisocoumarins are versatile building blocks for various dihydroisocoumarin derivatives in which the Br group can readily be modified to achieve biologically important 4-O-type and 4-N-type 3,4-dihydroisocoumarin systems. In addition, studies indicated that, by refining some parameters, the synthetically useful 5-exo phthalide products could be achieved with good yields and ee's.