2-formyl-5-((isobutoxycarbonyl)amino)benzoic acid | 1387557-77-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-formyl-5-((isobutoxycarbonyl)amino)benzoic acid
• CAS: 1387557-77-8
• 化学式: C₁₃H₁₅NO₅
• 分子量: 265.266
• InChiKey: UCTPTSCWBAMMJB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  92.7
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-formyl-5-((isobutoxycarbonyl)amino)benzoic acid 在 silver fluoride 、 potassium carbonate 、 (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.0h， 生成 (R)-isobutyl N-(3-allyl-1-oxo-1,3-dihydroisobenzofuran-5-yl)carbamate
  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
• 作为产物：
  描述：

  isobutyl (3-oxo-1,3-dihydroisobenzofuran-5-yl)carbamate 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 水 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 2.0h， 生成 2-formyl-5-((isobutoxycarbonyl)amino)benzoic acid
  参考文献：
  名称：

  An Indium-Mediated Allylative/Transesterification DFT-Directed Approach to Chiral C₍₃₎-Functionalized Phthalides

  摘要：

  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.

  DOI：

  10.1021/ol301566f