(1S,2R)-1-Benzoylamino-2-((S)-1,2-dihydroxy-ethyl)-4-oxo-cyclohexanecarboxylic acid methyl ester | 178976-48-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1S,2R)-1-Benzoylamino-2-((S)-1,2-dihydroxy-ethyl)-4-oxo-cyclohexanecarboxylic acid methyl ester
• CAS: 178976-48-2
• 化学式: C₁₇H₂₁NO₆
• 分子量: 335.357
• InChiKey: YDVYSVSTPMILRK-VBQJREDUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.05
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  112.93
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (1S,2R)-1-Benzoylamino-2-((S)-1,2-dihydroxy-ethyl)-4-oxo-cyclohexanecarboxylic acid methyl ester 在 ruthenium trichloride 、 sodium periodate 作用下， 以 四氯化碳 、 乙腈 为溶剂， 反应 48.0h， 以82%的产率得到(1S,2R)-1-Benzoylamino-4-oxo-cyclohexane-1,2-dicarboxylic acid 1-methyl ester
  参考文献：
  名称：

  Z-2-phenyl-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-ylmethylen]-5(4H)-oxazolone as the dienophile in asymmetric diels-alder reactions. II

  摘要：

  Diels-Alder reaction of Z-2-phenyl-4-[(S)-2,2-dimethyl-1,3-dioxolan -4-ylmethylen]-5(4H)-oxazolone and Danishefsky's diene is studied. Thermally induced reaction took place at room temperature with a high diastereofacial selectivity and Diels-Alder adducts, obtained in very high diastereomeric purity, were easily transformed into valuable compounds. The stereochemistry of the adducts has been elucidated by single crystal X-ray structure determinations, H-1-NMR analysis and mechanistic considerations. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00160-7
• 作为产物：
  描述：

  methyl (1R,6R)-1-benzamido-6-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>-4-oxo-2-cyclohexen-1-carboxylate 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 32.0h， 生成 (1S,2R)-1-Benzoylamino-2-((S)-1,2-dihydroxy-ethyl)-4-oxo-cyclohexanecarboxylic acid methyl ester
  参考文献：
  名称：

  Z-2-phenyl-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-ylmethylen]-5(4H)-oxazolone as the dienophile in asymmetric diels-alder reactions. II

  摘要：

  Diels-Alder reaction of Z-2-phenyl-4-[(S)-2,2-dimethyl-1,3-dioxolan -4-ylmethylen]-5(4H)-oxazolone and Danishefsky's diene is studied. Thermally induced reaction took place at room temperature with a high diastereofacial selectivity and Diels-Alder adducts, obtained in very high diastereomeric purity, were easily transformed into valuable compounds. The stereochemistry of the adducts has been elucidated by single crystal X-ray structure determinations, H-1-NMR analysis and mechanistic considerations. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00160-7