(4aS,8aS)-2-Methoxycarbonylhexahydro-6-isoquinolone

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: (4aS,8aS)-2-Methoxycarbonylhexahydro-6-isoquinolone
• 英文别名: methyl (4aS,8aS)-6-oxo-1,3,4,4a,5,8a-hexahydroisoquinoline-2-carboxylate
• 化学式: C₁₁H₁₅NO₃
• 分子量: 209.245
• InChiKey: ROGCCPQGWXPRAU-IUCAKERBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (3R,4S)-4-tert-Butoxycarbonylmethyl-3-vinyl-piperidine-1-carboxylic acid methyl ester 以 硫酸 为溶剂， 生成 (4aS,8aS)-2-Methoxycarbonylhexahydro-6-isoquinolone
  参考文献：
  名称：

  A novel, stereoselective synthesis of cis,4a (S), 8a(R)-decahydro-6(2H)-isoquinolones from meroquinene esters

  摘要：

  Intramolecular cyclization of N-acylated meroquinene t-butyl esters in cold H2SO4 cleanly afforded cis-4a(S), 8a(R)-decahydro-6(2H)-isoquinolones with complete stereocontrol in >95% yield. Formation of the meroquinene esters from cinchona alkaloid autoxidation using an improved Doering protocol was accomplished in three steps with 85% overall yield.

  DOI：

  10.1016/s0040-4039(00)73922-0

文献信息

• Stereocontrolled synthesis of cis-bicyclic compounds
  申请人：ELI LILLY AND COMPANY

  公开号：EP0618196A1

  公开（公告）日：1994-10-05

  This invention provides a process for the stereocontrolled synthesis of cis-bicyclic compounds, including cis-hexahydro-6-isoquinolones, cis-dihydroisochromanones, cis-dihydrothiochromanones, and cis-bicyclo[4.4.0]dec-3-ene-2-ones.

  本发明提供了一种立体控制合成顺式双环化合物的工艺，包括顺式六氢-6-异喹啉酮、顺式二氢异色满酮、顺式二氢硫代色满酮和顺式双环[4.4.0]癸-3-烯-2-酮。
• Synthesis of CIS-decahydroisoquinoline-3-carboxylic acids
  申请人：ELI LILLY AND COMPANY

  公开号：EP0618197A1

  公开（公告）日：1994-10-05

  This invention provides a process for the synthesis of cis-decahydroisoquinoline-3-carboxylic acids and provides intermediates in the synthesis thereof.

  本发明提供了一种合成顺式-十氢异喹啉-3-羧酸的工艺，并提供了合成过程中的中间体。
• US5461156A
  申请人：——

  公开号：US5461156A

  公开（公告）日：1995-10-24
• A novel, stereoselective synthesis of cis,4a (S), 8a(R)-decahydro-6(2H)-isoquinolones from meroquinene esters
  作者：Michael J. Martinelli、Barry C. Peterson、Vien V. Khau、Darrell R. Hutchicon、Kevin A. Sullivan

  DOI：10.1016/s0040-4039(00)73922-0

  日期：1993.1

  Intramolecular cyclization of N-acylated meroquinene t-butyl esters in cold H2SO4 cleanly afforded cis-4a(S), 8a(R)-decahydro-6(2H)-isoquinolones with complete stereocontrol in >95% yield. Formation of the meroquinene esters from cinchona alkaloid autoxidation using an improved Doering protocol was accomplished in three steps with 85% overall yield.