(3S,4R)-4-bromo-3-propyl-3,4-dihydroisochromen-1-one | 1354004-99-1

• 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: (3S,4R)-4-bromo-3-propyl-3,4-dihydroisochromen-1-one
• CAS: 1354004-99-1
• 化学式: C₁₂H₁₃BrO₂
• 分子量: 269.138
• InChiKey: APUUUYXGSVRHMV-WDEREUQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 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-(pent-1-en-1-yl)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 (R)-3-((S)-1-bromobutyl)isobenzofuran-1(3H)-one 、 (S)-3-((R)-1-bromobutyl)isobenzofuran-1(3H)-one 、 、 (3S,4R)-4-bromo-3-propyl-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

• 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.