(-)-(1'S,4aS,8aR)-4a-ethyl-1-(1'-phenylethyl)perhydroquinolin-7-one | 402852-54-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉类
• 英文名称: (-)-(1'S,4aS,8aR)-4a-ethyl-1-(1'-phenylethyl)perhydroquinolin-7-one
• 英文别名: (-)-(1'S,4aS,8aR)-4a-ethyl-1-(1'-phenylethyl)octahydroquinolin-7-one；(4aS,8aR)-4a-ethyl-1-[(1S)-1-phenylethyl]-3,4,5,6,8,8a-hexahydro-2H-quinolin-7-one
• CAS: 402852-54-4
• 化学式: C₁₉H₂₇NO
• 分子量: 285.429
• InChiKey: CTDZAAJTBGREAO-IPELMVKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (-)-(1'S,4aS,8aR)-4a-ethyl-1-(1'-phenylethyl)perhydroquinolin-7-one 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 甲醇 为溶剂， 以90%的产率得到(4aS,8aR)-4a-ethyldecahydroquinolin-7-one
  参考文献：
  名称：

  Synthesis of (−)-(1′S,4aS,8aR)- and (+)-(1′S,4aR,8aS)-4a-ethyl-1-(1′-phenylethyl)-octahydroquinolin-7-ones

  摘要：

  A synthesis of the enamine (-)-(1'S)-5-ethyl-1-(1'-phenylethyl)-1,2,3,4-tetrahydropyridine 4 and its application in a synthesis of (-)-(1'S,4aS,8aR)- and (+)-(1'S,4aR,8aS)-4a-ethyl-1-(1'-phenylethyl)-octahydroquinolin-7-ones 5 and 6 is described. In addition, an X-ray study of 6 is reported. Finally, the preparation of (4aS,8aR)-4a-ethyl-octahydroquinolin-7-one 7 is described. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00391-3
• 作为产物：
  描述：

  甲基4-甲酰基己酸酯 在 氢氧化钾 、 lithium aluminium tetrahydride 、 18-冠醚-6 、 4-甲基苯磺酸吡啶 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 生成 (-)-(1'S,4aS,8aR)-4a-ethyl-1-(1'-phenylethyl)perhydroquinolin-7-one
  参考文献：
  名称：

  Synthesis of (−)-(1′S,4aS,8aR)- and (+)-(1′S,4aR,8aS)-4a-ethyl-1-(1′-phenylethyl)-octahydroquinolin-7-ones

  摘要：

  A synthesis of the enamine (-)-(1'S)-5-ethyl-1-(1'-phenylethyl)-1,2,3,4-tetrahydropyridine 4 and its application in a synthesis of (-)-(1'S,4aS,8aR)- and (+)-(1'S,4aR,8aS)-4a-ethyl-1-(1'-phenylethyl)-octahydroquinolin-7-ones 5 and 6 is described. In addition, an X-ray study of 6 is reported. Finally, the preparation of (4aS,8aR)-4a-ethyl-octahydroquinolin-7-one 7 is described. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00391-3

文献信息

• (–)-(1′<i>S</i>,4a<i>S</i>,7<i>R</i>,8a<i>R</i>)-4a-Ethyl-7-hydroxy-1-(1′-phenylethyl)perhydroquinolinium bromide
  作者：Edna Vázquez、Alberto Galindo、Sylvain Bernès、Dino Gnecco

  DOI：10.1107/s0108270102014725

  日期：2002.10.15

  In the structure of the title compound, C(19)H(30)NO(+).Br(-), the rings of the perhydroquinolinium moiety are cis fused. The successful reduction of the ketone functionality of the quinolinone used as starting material is confirmed by the hydroxy C-O bond length of 1.428 (3) A.

  在标题化合物C（19）H（30）NO（+）。Br（-）的结构中，全氢喹啉部分的环是顺式稠合的。羟基CO键长为1.428（3）A，证实成功降低了用作原料的喹啉酮的酮官能度。
• Unexpected retro-Michael reaction of (−)-(1′S,4aS,8aR)- and (+)-(1′S,4aR,8aS)-4a-ethyl-1-(1-phenylethyl)octahydroquinolin-7-ones
  作者：E. Vázquez、A. Galindo、D. Gnecco、S. Bernès、J.L. Terán、R.G. Enrı́quez

  DOI：10.1016/s0957-4166(02)00003-4

  日期：2001.12

  An unexpected retro-Michael reaction of (-)-(1'S,4aS,8aR)- and (+)-(1'S,4aR, 8aS)-4a-ethyl-1-(1'-phenylethyl)octahydroquinolin-7-ones 1 and 2 is described. In addition, a diastererospecific intramolecular Michael reaction of 3.HCl and 4.HCl is reported. (C) 2002 Elsevier Science Ltd. All rights reserved.