(R)-3-allyl-6-bromoisobenzofuran-1(3H)-one | 1387557-73-4

• 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-allyl-6-bromoisobenzofuran-1(3H)-one
• 英文别名: (3R)-6-bromo-3-prop-2-enyl-3H-2-benzofuran-1-one
• CAS: 1387557-73-4
• 化学式: C₁₁H₉BrO₂
• 分子量: 253.095
• InChiKey: OFURFCXKXCLACO-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  苯酞 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 硫酸 、 silver fluoride 、 potassium carbonate 、 (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl 、 三氟乙酸 作用下， 以 甲醇 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 82.0h， 生成 (S)-3-allyl-6-bromoisobenzofuran-1(3H)-one 、 (R)-3-allyl-6-bromoisobenzofuran-1(3H)-one
  参考文献：
  名称：

  A synthetic route to chiral C(3)-functionalized phthalides via a Ag(I)-catalyzed allylation/transesterification sequence

  摘要：

  A Ag(I)-catalyzed synthesis of chiral C-(3)-substituted phthalides (8a-f) via a Sakurai-Hosomi allylation/transesterification reaction is described (ee <= 86%). A notable feature of this reaction is that it utilizes ortho-substituted aldehydes, which are a class of compounds that generally afford poor levels of stereoinduction when applying most known catalytic asymmetric allylation approaches. It was also found that elongation of the n-alkyl chain length (R-1, up to n=6; R-2=H) of the starting alkyl 2-formylbenzoates (7g-i) improved the enantiomeric excess (ee) of the product. Crown Copyright (C) 2013 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.02.002

文献信息

• An Indium-Mediated Allylative/Transesterification DFT-Directed Approach to Chiral C₍₃₎-Functionalized Phthalides
  作者：Roya Mirabdolbaghi、Travis Dudding

  DOI：10.1021/ol301566f

  日期：2012.7.20

  A one-pot synthesis of chiral C-(3)-substituted phthalides via an indium-mediated allylation/transesterification reaction is described. The development of this reaction was facilitated through the applied use of DFT calculations to rationalize the stereoselection of a chiral In-mediated process. It was discovered that the enantiomeric excess of this reaction depended upon the steric size, chain length, and substitution of the aldehyde employed.