3-N-[(1S,2R)-2-(3-nicotinoyloxymethyl)cyclohexyl]carbamoylpyridine | 203064-43-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3-N-[(1S,2R)-2-(3-nicotinoyloxymethyl)cyclohexyl]carbamoylpyridine
• 英文别名: [(1R,2S)-2-(pyridine-3-carbonylamino)cyclohexyl]methyl pyridine-3-carboxylate
• CAS: 203064-43-1
• 化学式: C₁₉H₂₁N₃O₃
• 分子量: 339.394
• InChiKey: IXHFLXQQZYZLAP-IRXDYDNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  81.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-N-[(1S,2R)-2-(3-nicotinoyloxymethyl)cyclohexyl]carbamoylpyridine 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 0.17h， 以90%的产率得到3-N-[(1S,2R)-2-hydroxymethylcyclohexyl]carbamoylpyridine
  参考文献：
  名称：

  Rational de novo design of NADH mimic for stereoselective reduction based on molecular orbital calculation

  摘要：

  The methodology of rational design of NADH mimics in stereoselective reduction of carbonyl and imino groups based on molecular orbital calculation was described. The designed NADH mimics la and Ib were subjected to the reduction of benzoylformate and acetyliminophenylacetate. As expected from the calculations of the transition-states, the reduction with la proceeded with high stereoselectivity in both substrates, while Ib showed much lower chirality transfer. (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(97)10294-0
• 作为产物：
  描述：

  (-)-顺式-2-苄胺基环己基羧酸 在 sodium hydroxide 、 sodium tetrahydroborate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 48.5h， 生成 3-N-[(1S,2R)-2-(3-nicotinoyloxymethyl)cyclohexyl]carbamoylpyridine
  参考文献：
  名称：

  Rational de novo design of NADH mimic for stereoselective reduction based on molecular orbital calculation

  摘要：

  The methodology of rational design of NADH mimics in stereoselective reduction of carbonyl and imino groups based on molecular orbital calculation was described. The designed NADH mimics la and Ib were subjected to the reduction of benzoylformate and acetyliminophenylacetate. As expected from the calculations of the transition-states, the reduction with la proceeded with high stereoselectivity in both substrates, while Ib showed much lower chirality transfer. (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(97)10294-0

文献信息

• Rational de novo design of NADH mimic for stereoselective reduction based on molecular orbital calculation
  作者：Tadashi Eguchi、Miki Fukuda、Yumiko Toyooka、Katsumi Kakinuma

  DOI：10.1016/s0040-4020(97)10294-0

  日期：1998.1

  The methodology of rational design of NADH mimics in stereoselective reduction of carbonyl and imino groups based on molecular orbital calculation was described. The designed NADH mimics la and Ib were subjected to the reduction of benzoylformate and acetyliminophenylacetate. As expected from the calculations of the transition-states, the reduction with la proceeded with high stereoselectivity in both substrates, while Ib showed much lower chirality transfer. (C) 1997 Elsevier Science Ltd. All rights reserved.