benzoic acid 2-[(2R)-[(1S)-3-oxo-1,3-dihydroisobenzofuran-1-yl]pyrrolidin-1-yl]-(2R)-2-phenylethyl ester | 639503-08-5

• 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: benzoic acid 2-[(2R)-[(1S)-3-oxo-1,3-dihydroisobenzofuran-1-yl]pyrrolidin-1-yl]-(2R)-2-phenylethyl ester
• 英文别名: [(2R)-2-[(2R)-2-[(1S)-3-oxo-1H-2-benzofuran-1-yl]pyrrolidin-1-yl]-2-phenylethyl] benzoate
• CAS: 639503-08-5
• 化学式: C₂₇H₂₅NO₄
• 分子量: 427.5
• InChiKey: RXVPCICDGKCBMM-DSITVLBTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  benzoic acid 2-[(2R)-[(1S)-3-oxo-1,3-dihydroisobenzofuran-1-yl]pyrrolidin-1-yl]-(2R)-2-phenylethyl ester 在 palladium dihydroxide 氢气 、 sodium acetate 作用下， 反应 72.0h， 以54%的产率得到10-hydroxy-(10S,10aR)-2,3,10,10a-tetrahydro-1H-pyrrolo[1,2-b]isoquinolin-5-one
  参考文献：
  名称：

  Asymmetric routes towards polyfunctionalized pyrrolidines: application to the synthesis of alkaloid analogues

  摘要：

  The Mukaiyama aldol type condensation of t-butyldimethylsilyloxypyrrole 1b with methyl 2-formylbenzoate furnished the aldol adduct 9 with high yield and complete stereoselectivity. An erythro (anti) configuration was established (X-ray) in sharp contrast with the reaction of 1b with aliphatic aldehydes. Simple chemical transformations were used to transform 9 into original phthalidopyrrolidine compound analogous of bicuculline alkaloids. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00592-5
• 作为产物：
  描述：

  2-醛基苯甲酸甲酯 在 palladium on activated charcoal 三氟化硼四氢呋喃络合物 、 三氟化硼乙醚 、 氢气 、 silica gel 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 10.0h， 生成 benzoic acid 2-[(2R)-[(1S)-3-oxo-1,3-dihydroisobenzofuran-1-yl]pyrrolidin-1-yl]-(2R)-2-phenylethyl ester
  参考文献：
  名称：

  Asymmetric routes towards polyfunctionalized pyrrolidines: application to the synthesis of alkaloid analogues

  摘要：

  The Mukaiyama aldol type condensation of t-butyldimethylsilyloxypyrrole 1b with methyl 2-formylbenzoate furnished the aldol adduct 9 with high yield and complete stereoselectivity. An erythro (anti) configuration was established (X-ray) in sharp contrast with the reaction of 1b with aliphatic aldehydes. Simple chemical transformations were used to transform 9 into original phthalidopyrrolidine compound analogous of bicuculline alkaloids. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00592-5

文献信息

• Asymmetric routes towards polyfunctionalized pyrrolidines: application to the synthesis of alkaloid analogues
  作者：Martial Toffano、Bruno Dudot、Anne Zaparucha、Jacques Royer、Mireille Sevrin、Pascal George、Angèle Chiaroni

  DOI：10.1016/s0957-4166(03)00592-5

  日期：2003.10

  The Mukaiyama aldol type condensation of t-butyldimethylsilyloxypyrrole 1b with methyl 2-formylbenzoate furnished the aldol adduct 9 with high yield and complete stereoselectivity. An erythro (anti) configuration was established (X-ray) in sharp contrast with the reaction of 1b with aliphatic aldehydes. Simple chemical transformations were used to transform 9 into original phthalidopyrrolidine compound analogous of bicuculline alkaloids. (C) 2003 Elsevier Ltd. All rights reserved.