(2E,4E)-5-Cyclohexyl-penta-2,4-dienoic acid ((1R,5R,6R)-5-hydroxy-2-oxo-7-oxa-bicyclo[4.1.0]hept-3-en-3-yl)-amide | 211997-75-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2E,4E)-5-Cyclohexyl-penta-2,4-dienoic acid ((1R,5R,6R)-5-hydroxy-2-oxo-7-oxa-bicyclo[4.1.0]hept-3-en-3-yl)-amide
• 英文别名: (2E,4E)-5-cyclohexyl-N-[(1R,5R,6R)-5-hydroxy-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]penta-2,4-dienamide
• CAS: 211997-75-0
• 化学式: C₁₇H₂₁NO₄
• 分子量: 303.358
• InChiKey: MHYOIQHRCBJOKV-AYAFIWDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  78.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2E,4E)-5-Cyclohexyl-penta-2,4-dienoic acid ((1R,5R,6R)-5-hydroxy-2-oxo-7-oxa-bicyclo[4.1.0]hept-3-en-3-yl)-amide 在 重铬酸吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 2-(5-cyclohexylpenta-2'E,4'E-dienoylamino)-5,6-epoxy-1,4-benzoquinone
  参考文献：
  名称：

  Asymmetric synthesis of the mC7N core of the manumycin family: Preparation of (+)-MT 35214 and a formal total synthesis of (−)-alisamycin

  摘要：

  An asymmetric approach to the mC(7)N epoxyquinone central unit of the manumycin antibiotics is described based on the enantioselective (89% ee) chiral phase transfer epoxidation of a substituted cyclohexenone. The chiral epoxide is employed in the first syntheses of the tide compounds in enantiomerically pure form. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01047-8
• 作为产物：
  描述：

  3-amino-4,4-dimethoxy-5,6-epoxycyclohex-2-en-1-on 在 Montmorillonite K₁₀ 、 三乙基硼氢化锂 、 lithium tert-butoxide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (2E,4E)-5-Cyclohexyl-penta-2,4-dienoic acid ((1R,5R,6R)-5-hydroxy-2-oxo-7-oxa-bicyclo[4.1.0]hept-3-en-3-yl)-amide
  参考文献：
  名称：

  Asymmetric synthesis of the mC7N core of the manumycin family: Preparation of (+)-MT 35214 and a formal total synthesis of (−)-alisamycin

  摘要：

  An asymmetric approach to the mC(7)N epoxyquinone central unit of the manumycin antibiotics is described based on the enantioselective (89% ee) chiral phase transfer epoxidation of a substituted cyclohexenone. The chiral epoxide is employed in the first syntheses of the tide compounds in enantiomerically pure form. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01047-8

文献信息

• Asymmetric synthesis of the mC7N core of the manumycin family: Preparation of (+)-MT 35214 and a formal total synthesis of (−)-alisamycin
  作者：Gregor Macdonald、Lilian Alcaraz、Norman J Lewis、Richard J.K Taylor

  DOI：10.1016/s0040-4039(98)01047-8

  日期：1998.7

  An asymmetric approach to the mC(7)N epoxyquinone central unit of the manumycin antibiotics is described based on the enantioselective (89% ee) chiral phase transfer epoxidation of a substituted cyclohexenone. The chiral epoxide is employed in the first syntheses of the tide compounds in enantiomerically pure form. (C) 1998 Elsevier Science Ltd. All rights reserved.