(3S,4R)-3-[3,5-bis(trifluoromethyl)phenyl]-4-bromo-3,4-dihydroisochromen-1-one | 1354004-95-7

• 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: (3S,4R)-3-[3,5-bis(trifluoromethyl)phenyl]-4-bromo-3,4-dihydroisochromen-1-one
• CAS: 1354004-95-7
• 化学式: C₁₇H₉BrF₆O₂
• 分子量: 439.152
• InChiKey: VEMSRZOROIITSP-KGLIPLIRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  26
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  (E)-2-[3,5-bis(trifluoromethyl)styryl]benzoic acid 在 N-溴代丁二酰亚胺(NBS) 、 三苯基瞵硫 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 (3S,4R)-3-[3,5-bis(trifluoromethyl)phenyl]-4-bromo-3,4-dihydroisochromen-1-one 、 (S)-3-((R)-[3,5-bis(trifluoromethyl)phenyl]bromomethyl)-isobenzofuran-1(3H)-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