(E)-N-(2-methyl-1-methylene-4-methoxy-2-butenyl)-2-(S)-methoxymethylpyrrolidine | 149199-19-9

• 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: (E)-N-(2-methyl-1-methylene-4-methoxy-2-butenyl)-2-(S)-methoxymethylpyrrolidine
• 英文别名: (2S)-2-(methoxymethyl)-1-[(3E)-5-methoxy-3-methylpenta-1,3-dien-2-yl]pyrrolidine
• CAS: 149199-19-9
• 化学式: C₁₃H₂₃NO₂
• 分子量: 225.331
• InChiKey: PNPNSESLSBYTGU-HJTPGIPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-N-(2-methyl-1-methylene-4-methoxy-2-butenyl)-2-(S)-methoxymethylpyrrolidine 在 盐酸 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 32.0h， 生成 (1R,3S,4R,5S,6R)-6-(2-furyl)-5-(methyoxymethyl)-4-methyl-1,3-cycloheptanediol
  参考文献：
  名称：

  Stereoselective Synthesis of Seven-Membered Carbocycles from 2-Amino-1,3-butadienes and Vinyl Chromium Fischer-Type Carbenes

  摘要：

  Seven-membered ring carbocycles are prepared by reaction of easily avaliable 2-amino-1,3-butadienes with vinyl Fischer carbenes. Hydrolysis of the cycloadduct initially formed gives rise to cyclohepta-1,3-diones with total regio- and stereoselectivity in a one-pot process. When 2-aminobutadienes bearing a prolinol derivative as a chiral auxiliary are used, the corresponding cyclic diketones are obtained with very high enantiomeric excesses. The absolute configuration of the stereogenic centers generated was determined with the aid of ROESY and CD measurements.

  DOI：

  10.1021/ja00142a006
• 作为产物：
  描述：

  (S)-(+)-2-(甲氧基甲基)吡唑烷 、 (E)-5-甲氧基-3-甲基-3-戊烯-1-炔 在 mercury(II) diacetate 作用下， 以 乙醚 为溶剂， 以67%的产率得到(E)-N-(2-methyl-1-methylene-4-methoxy-2-butenyl)-2-(S)-methoxymethylpyrrolidine
  参考文献：
  名称：

  Barluenga, Jose; Aznar, Fernando; Ribas, Cristina, Chemistry - A European Journal, 1996, vol. 2, # 7, p. 805 - 811

  摘要：

  DOI：

文献信息

• Cycloaddition Reactions of Chiral 2-Amino-1,3-butadienes with Nitroalkenes:  Synthesis of Enantiomerically Pure 4-Nitrocyclohexanones¹
  作者：José Barluenga、Fernando Aznar、Cristina Ribas、Carlos Valdés

  DOI：10.1021/jo970237m

  日期：1997.10.1

  2-Amino-1,3-butadienes bearing commercially available S-(+)-2-(methoxymethyl)pyrrolidine as chiral auxiliary undergo a [4 + 2] cycloaddition reaction with nitroalkenes to furnish 4-nitrocyclohexanones upon hydrolysis of the resulting enamine. The cycloadducts are obtained with good yields and very high enantiomeric excesses. The reaction has been performed with aromatic and aliphatic conjugated nitroalkenes. Moreover, a 2-amino diene which features a (Z) double bond undergoes a Michael addition reaction with nitroalkenes, which gives rise to open chain compounds with high enantioselectivity. After acidic hydrolysis, the open chain compounds cyclize to form chiral substituted furans.
• 2-Amino-1,3-butadienes as chiral building blocks: enantioselective synthesis of 4-piperidones, 4-nitrocyclohexanones, and 1,3-cycloheptadione derivatives
  作者：Jose Barluenga、Fernando Aznar、Carlos Valdes、Alfredo Martin、Santiago Garcia-Granda、Eduardo Martin

  DOI：10.1021/ja00063a085

  日期：1993.5
• Barluenga, Jose; Aznar, Fernando; Ribas, Cristina, Chemistry - A European Journal, 1996, vol. 2, # 7, p. 805 - 811
  作者：Barluenga, Jose、Aznar, Fernando、Ribas, Cristina、Valdes, Carlos、Fernandez, Monica、et al.

  DOI：——

  日期：——
• Stereoselective Synthesis of Seven-Membered Carbocycles from 2-Amino-1,3-butadienes and Vinyl Chromium Fischer-Type Carbenes
  作者：Jose Barluenga、Fernando Aznar、Alfredo Martin、Jesus T. Vazquez

  DOI：10.1021/ja00142a006

  日期：1995.9

  Seven-membered ring carbocycles are prepared by reaction of easily avaliable 2-amino-1,3-butadienes with vinyl Fischer carbenes. Hydrolysis of the cycloadduct initially formed gives rise to cyclohepta-1,3-diones with total regio- and stereoselectivity in a one-pot process. When 2-aminobutadienes bearing a prolinol derivative as a chiral auxiliary are used, the corresponding cyclic diketones are obtained with very high enantiomeric excesses. The absolute configuration of the stereogenic centers generated was determined with the aid of ROESY and CD measurements.