methyl 2-[(S)-[(2R)-1-[(1R)-2-benzoyloxy-1-phenylethyl]-5-oxo-2H-pyrrol-2-yl]-hydroxymethyl]benzoate | 639503-02-9

• 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: methyl 2-[(S)-[(2R)-1-[(1R)-2-benzoyloxy-1-phenylethyl]-5-oxo-2H-pyrrol-2-yl]-hydroxymethyl]benzoate
• CAS: 639503-02-9
• 化学式: C₂₈H₂₅NO₆
• 分子量: 471.51
• InChiKey: LIYPRSYOOAHLRU-USZFVNFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  93.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 2-[(S)-[(2R)-1-[(1R)-2-benzoyloxy-1-phenylethyl]-5-oxo-2H-pyrrol-2-yl]-hydroxymethyl]benzoate 在 palladium on activated charcoal 氢气 、 silica gel 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 benzoic acid 2-[2-oxo-(5R)-[(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
• 作为产物：
  描述：

  2-醛基苯甲酸甲酯 、 (2R)-2-<2-(tert-Butyldimethylsiloxy)pyrrol-1-yl>-2-phenylethylbenzoate 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以95%的产率得到methyl 2-[(S)-[(2R)-1-[(1R)-2-benzoyloxy-1-phenylethyl]-5-oxo-2H-pyrrol-2-yl]-hydroxymethyl]benzoate
  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.