N-[(2S)-2-(methoxymethyl)pyrrolidin-1-yl]-3-methylbutan-2-imine | 65651-54-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: N-[(2S)-2-(methoxymethyl)pyrrolidin-1-yl]-3-methylbutan-2-imine
• CAS: 65651-54-9
• 化学式: C₁₁H₂₂N₂O
• 分子量: 198.308
• InChiKey: AHJNGHNKOITRSP-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.13
• 重原子数：
  14.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  24.83
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N-[(2S)-2-(methoxymethyl)pyrrolidin-1-yl]-3-methylbutan-2-imine 在 臭氧 作用下， 以 二氯甲烷 为溶剂， 生成 ((S)-1-Benzyl-2-isopropyl-5-methyl-4-oxo-hexyl)-phosphonic acid diethyl ester
  参考文献：
  名称：

  Diastereo- and enantioselective synthesis of 2,3- and 1,2-disubstituted 4-oxophosphonates via asymmetric Michael addition

  摘要：

  Asymmetric Michael addition of lithiated SAMP hydrazones (S)-2 to a variety of alkenylphosphonates (E)-3 followed by oxidative cleavage of the 1,4-adducts 4 afforded 2,3-disubstituted 4-oxophosphonates 5 with good to very good yields (58-80%), low to moderate diastereomeric (de = 6-74%) and excellent enantiomeric excesses (ee = >93%). Pure anti-diastereomers (ee = >93%) of 5 were obtained by separation of the stereoisomers by HPLC. In addition, the lithiated SAMP hydrazone (S)-2a was added to alkenylphosphonates (E)-3, and the lithio phosphonate anions were trapped with alkyl halides or sulfates, yielding 1,2-disubstituted 4-oxophosphonates 8 with moderate to good yields (38-69%), low to good diastereomeric (de = 10-77%) and high enantiomeric excesses (ee = >90%) after oxidative cleavage. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00814-4
• 作为产物：
  描述：

  3-甲基-2-丁酮 、 (S)-1-amino-2-(methoxymethyl)pyrrolidine 生成 N-[(2S)-2-(methoxymethyl)pyrrolidin-1-yl]-3-methylbutan-2-imine
  参考文献：
  名称：

  Asymmetric synthesis of β-substituted δ-ketoesters via michael-additions of samp/ramp-hydrazones to α,β-unsaturated esters, virtually complete 1.6-asymmetric induction

  摘要：

  DOI：

  10.1016/s0040-4039(01)99823-5

文献信息

• Enders, Dieter; Wahl, Heiner; Papadopoulos, Kyriakos, Liebigs Annalen, 1995, # 7, p. 1177 - 1184
  作者：Enders, Dieter、Wahl, Heiner、Papadopoulos, Kyriakos

  DOI：——

  日期：——
• Asymmetric synthesis of β-substituted δ-ketoesters via michael-additions of samp/ramp-hydrazones to α,β-unsaturated esters, virtually complete 1.6-asymmetric induction
  作者：Dieter Enders、Kyriakos Papadopoulos

  DOI：10.1016/s0040-4039(01)99823-5

  日期：1983.1
• Diastereo- and enantioselective synthesis of 2,3- and 1,2-disubstituted 4-oxophosphonates via asymmetric Michael addition
  作者：Dieter Enders、Heiner Wahl、Kyriakos Papadopoulos

  DOI：10.1016/s0040-4020(97)00814-4

  日期：1997.9

  Asymmetric Michael addition of lithiated SAMP hydrazones (S)-2 to a variety of alkenylphosphonates (E)-3 followed by oxidative cleavage of the 1,4-adducts 4 afforded 2,3-disubstituted 4-oxophosphonates 5 with good to very good yields (58-80%), low to moderate diastereomeric (de = 6-74%) and excellent enantiomeric excesses (ee = >93%). Pure anti-diastereomers (ee = >93%) of 5 were obtained by separation of the stereoisomers by HPLC. In addition, the lithiated SAMP hydrazone (S)-2a was added to alkenylphosphonates (E)-3, and the lithio phosphonate anions were trapped with alkyl halides or sulfates, yielding 1,2-disubstituted 4-oxophosphonates 8 with moderate to good yields (38-69%), low to good diastereomeric (de = 10-77%) and high enantiomeric excesses (ee = >90%) after oxidative cleavage. (C) 1997 Elsevier Science Ltd.