(2S,5RS)-methyl 1-methoxycarbonyl-5-phenyl-pyrrolidine-2-carboxylate | 909405-19-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S,5RS)-methyl 1-methoxycarbonyl-5-phenyl-pyrrolidine-2-carboxylate
• 英文别名: methyl (2S,5RS)-1-methoxycarbonyl-5-phenylprolinate；dimethyl (2S)-5-phenylpyrrolidine-1,2-dicarboxylate
• CAS: 909405-19-2
• 化学式: C₁₄H₁₇NO₄
• 分子量: 263.293
• InChiKey: HCFJDLUKVUUWSV-KIYNQFGBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,5RS)-methyl 1-methoxycarbonyl-5-phenyl-pyrrolidine-2-carboxylate 在 sodium hydroxide 、 碘代三甲硅烷 作用下， 以 甲醇 为溶剂， 生成 cis-N-formyl-α'-phenyl-L-proline
  参考文献：
  名称：

  New Efficient Organic Activators for Highly Enantioselective Reduction of Aromatic Ketones by Trichlorosilane

  摘要：

  Aryl ketones were reduced to the corresponding alcohols with excellent enantioselectivity (up to 99.7% ee) by Cl3SiH in the presence of a catalytic amount of N-formyl-alpha '-(2,4,6-triethylphenyl)-L-proline as an activator. Both carboxyl group at the alpha-position of the activator and 2,4,6-triethylphenyl group at the alpha '-position were critical for the high enantioselectivity.

  DOI：

  10.1021/ol0613822
• 作为产物：
  描述：

  在 palladium on activated charcoal 氢气 作用下， 生成 (2S,5RS)-methyl 1-methoxycarbonyl-5-phenyl-pyrrolidine-2-carboxylate
  参考文献：
  名称：

  New Efficient Organic Activators for Highly Enantioselective Reduction of Aromatic Ketones by Trichlorosilane

  摘要：

  Aryl ketones were reduced to the corresponding alcohols with excellent enantioselectivity (up to 99.7% ee) by Cl3SiH in the presence of a catalytic amount of N-formyl-alpha '-(2,4,6-triethylphenyl)-L-proline as an activator. Both carboxyl group at the alpha-position of the activator and 2,4,6-triethylphenyl group at the alpha '-position were critical for the high enantioselectivity.

  DOI：

  10.1021/ol0613822

文献信息

• Pyrrolidine and thiazolidine derivatives, their preparation and
  申请人：Rhone-Poulenc Rorer S.A.

  公开号：US05610144A1

  公开（公告）日：1997-03-11

  This invention relates to compositions of formula: ##STR1## and their salts, their preparation and the medicaments containing them.

  这项发明涉及以下结构的化合物：##STR1##及其盐，它们的制备以及含有它们的药物。
• Enantiospecific synthesis and absolute configuration of (+)-RP 66803 a new non-peptide CCK antagonist
  作者：Franco Manfré、Jean Pierre Pulicani

  DOI：10.1016/s0957-4166(00)86178-9

  日期：1994.1

  Pyrrolidine derivatives have been identified as a new class of non-peptide CCK antagonists. Enantiomers of RP 66803, a representative compound of this chemical family were previously prepared by chiral chromatography of the racemate. In order to determine the absolute configuration of each one, we report herein an enantiospecific synthesis leading to the (+)-isomer using anodic methoxylation as key

  吡咯烷衍生物已被鉴定为一类新的非肽CCK拮抗剂。RP 66803的对映异构体是该化学家族的代表化合物，先前已通过外消旋体的手性色谱法进行了制备。为了确定每一个的绝对构型，我们在本文中报道了使用阳极甲氧基化作为关键步骤的导致（+）-异构体的对映体特异性合成。