(E)-N-(2-methyl-1-methylene-4-(trimethylsiloxy)-2-butenyl)-N-methylaniline | 135523-32-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (E)-N-(2-methyl-1-methylene-4-(trimethylsiloxy)-2-butenyl)-N-methylaniline
• 英文别名: (E)-N-<2-methyl-1-methylene-4-<(trimethylsilyl)oxy>2-butenyl>-N-methylaniline；(E)-N-<2-methoxy-1-methylene-4-<(trimethylsilyl)oxy>-2-butenyl>-N-methylaniline；N-methyl-N-[(3E)-3-methyl-5-trimethylsilyloxypenta-1,3-dien-2-yl]aniline
• CAS: 135523-32-9
• 化学式: C₁₆H₂₅NOSi
• 分子量: 275.466
• InChiKey: ASBQXCOUWMKLRX-WYMLVPIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.43
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-N-(2-methyl-1-methylene-4-(trimethylsiloxy)-2-butenyl)-N-methylaniline 在 盐酸 、 碳酸氢钠 、 potassium carbonate 、 三乙胺 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 为溶剂， 反应 14.33h， 生成 (1R*,5S*,6S*)-1-aza-2-(2-furyl)-5-methyl-8-oxa-4,9-dioxobicyclo<4.3.0>nonane
  参考文献：
  名称：

  Stereoselective synthesis of 4-piperidone and 4-aminotetrahydropyridine derivatives by the imino Diels-Alder reaction of 2-amino-1,3-butadienes

  摘要：

  2-Amino-4-(alkoxymethyl)-1,3-butadienes react smoothly with nonactivated aldimines derived from aromatic aldehydes in the presence of ZnCl2 as Lewis acid giving rise, with good yields and very high stereoselectivity, to substituted 4-aminotetrahydropyridines which upon hydrolysis yield 4-piperidone derivatives. Moreover, the stereochemistry of the cyclization process depends on the nature of the N-substituent of the imine.

  DOI：

  10.1021/jo00064a030
• 作为产物：
  描述：

  3-甲基-2-戊烯-4-炔醇 在 mercury(II) diacetate 、 三乙胺 、 六甲基二硅氮烷 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 9.0h， 生成 (E)-N-(2-methyl-1-methylene-4-(trimethylsiloxy)-2-butenyl)-N-methylaniline
  参考文献：
  名称：

  Catalytic aminomercuration reactions of 3-alken-1-ynes: an improved method for the synthesis of 2-amino-1,3-butadienes and 1-aza-1,3-butadienes

  摘要：

  Catalytic aminomercuration of 3-alken-1-ynes leads to 1-aza-1,3-butadienes and 2-amino-1,3-butadienes. Under appropriate reaction conditions it is possible to prepare these compounds via mercuration of 3-alken-1-ynes in the presence of either aromatic or aliphatic primary and secondary amines. Depending on the substituents in the starting 3-alken-1-yne, the mercuration reaction may afford gamma-amino enamines instead of 2-amino-1,3-butadienes and 3-imino amines or 4-amino-1-aza-1,3-butadienes instead of 1-aza-1,3-butadienes.

  DOI：

  10.1021/jo00021a039

文献信息

• 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.
• Barluenga Jose, Aznar Fernando, Valdes Carlos, Cabal Marfa-Paz, J. Org. Chem., 58 (1993) N 12, S 3391-3396
  作者：Barluenga Jose, Aznar Fernando, Valdes Carlos, Cabal Marfa-Paz

  DOI：——

  日期：——
• Catalytic aminomercuration reactions of 3-alken-1-ynes: an improved method for the synthesis of 2-amino-1,3-butadienes and 1-aza-1,3-butadienes
  作者：Jose Barluenga、Fernando Aznar、Carlos Valdes、Maria Paz Cabal

  DOI：10.1021/jo00021a039

  日期：1991.10

  Catalytic aminomercuration of 3-alken-1-ynes leads to 1-aza-1,3-butadienes and 2-amino-1,3-butadienes. Under appropriate reaction conditions it is possible to prepare these compounds via mercuration of 3-alken-1-ynes in the presence of either aromatic or aliphatic primary and secondary amines. Depending on the substituents in the starting 3-alken-1-yne, the mercuration reaction may afford gamma-amino enamines instead of 2-amino-1,3-butadienes and 3-imino amines or 4-amino-1-aza-1,3-butadienes instead of 1-aza-1,3-butadienes.
• Stereoselective synthesis of 4-piperidone and 4-aminotetrahydropyridine derivatives by the imino Diels-Alder reaction of 2-amino-1,3-butadienes
  作者：Jose Barluenga、Fernando Aznar、Carlos Valdes、Maria Paz Cabal

  DOI：10.1021/jo00064a030

  日期：1993.6

  2-Amino-4-(alkoxymethyl)-1,3-butadienes react smoothly with nonactivated aldimines derived from aromatic aldehydes in the presence of ZnCl2 as Lewis acid giving rise, with good yields and very high stereoselectivity, to substituted 4-aminotetrahydropyridines which upon hydrolysis yield 4-piperidone derivatives. Moreover, the stereochemistry of the cyclization process depends on the nature of the N-substituent of the imine.