18-acetyl-16-oxa-18-azapentacyclo[6.6.5.02,7.09,14.015,19]nonadeca-2,4,6,9,11,13-hexaen-17-one | 65948-57-4

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 18-acetyl-16-oxa-18-azapentacyclo[6.6.5.02,7.09,14.015,19]nonadeca-2,4,6,9,11,13-hexaen-17-one
• CAS: 65948-57-4
• 化学式: C₁₉H₁₅NO₃
• 分子量: 305.333
• InChiKey: JDDZYKKDYJNUIW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.01
• 重原子数：
  23.0
• 可旋转键数：
  0.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  46.61
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  18-acetyl-16-oxa-18-azapentacyclo[6.6.5.02,7.09,14.015,19]nonadeca-2,4,6,9,11,13-hexaen-17-one 在 lithium phenylmethanethiolate 、 sodium hydride 、 caesium carbonate 作用下， 以 甲醇 为溶剂， 生成 (15S,19R)-16-oxa-18-azapentacyclo[6.6.5.02,7.09,14.015,19]nonadeca-2,4,6,9,11,13-hexaen-17-one
  参考文献：
  名称：

  Conformationally rigid chiral [4+2]cycloadduct-based 2-oxazolidinones as new auxiliaries

  摘要：

  Newly introduced enantiomerically pure [4 + 2]cycloadduct-based 2-oxazolidinones which are conformationally fixed by bicyclo[2.2.2] and [2.2.1] ring systems, serve well as exellent chiral auxiliaries in the Evans' asymmetric strategy.

  DOI：

  10.1016/0040-4039(91)80573-o
• 作为产物：
  描述：

  蒽 、 3-乙酰基噁唑烷-2-酮 生成 18-acetyl-16-oxa-18-azapentacyclo[6.6.5.02,7.09,14.015,19]nonadeca-2,4,6,9,11,13-hexaen-17-one
  参考文献：
  名称：

  Conformationally rigid chiral [4+2]cycloadduct-based 2-oxazolidinones as new auxiliaries

  摘要：

  Newly introduced enantiomerically pure [4 + 2]cycloadduct-based 2-oxazolidinones which are conformationally fixed by bicyclo[2.2.2] and [2.2.1] ring systems, serve well as exellent chiral auxiliaries in the Evans' asymmetric strategy.

  DOI：

  10.1016/0040-4039(91)80573-o

文献信息

• SCHOLZ K.-H.; HEINE H.-G.; HARTMANN W., J. LIEBIGS ANN. CHEM. <JLAC-BF>, 1977, NO 11-12, 2027-2035
  作者：SCHOLZ K.-H.、 HEINE H.-G.、 HARTMANN W.

  DOI：——

  日期：——
• Catalytic process for efficient enantiodivergence of meso-N,N′-diacetyl-2-imidazolidinones and D L-N-acetyl-2-oxazolidinones
  作者：Noriaki Hashimoto、Tadao Ishizuka、Takehisa Kunieda

  DOI：10.1016/s0040-4039(98)01340-9

  日期：1998.8

  A reductive monodeacylation, catalyzed by oxazaborolidines derived from conformationally rigid chiral aminoalcohols provideds a practical method for the effective enantiodivergence of meso-1,3-diacetyl-2-imidazolidinones. This catalytic deacylation is successfully applied to the kinetic resolution of racemic 1-acetyl-2-oxazolidinones. (C) 1998 Elsevier Science Ltd. All rights reserved.