(1S,2S,3R,4R,6S)-1-acetylmethyl-2,3-di-O-benzyl-4-hydroxy-6-nitrocyclohexane | 936112-28-6

• 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,2S,3R,4R,6S)-1-acetylmethyl-2,3-di-O-benzyl-4-hydroxy-6-nitrocyclohexane
• 英文别名: 1-[(1R,2S,3R,4R,6S)-4-hydroxy-6-nitro-2,3-bis(phenylmethoxy)cyclohexyl]propan-2-one
• CAS: 936112-28-6
• 化学式: C₂₃H₂₇NO₆
• 分子量: 413.47
• InChiKey: FPPVLXPZZDGVIW-ISBRNDMJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1S,2S,3R,4R,6S)-1-acetylmethyl-2,3-di-O-benzyl-4-hydroxy-6-nitrocyclohexane 、 溶剂黄146 在 锌 作用下， 以100%的产率得到(2R,3aR,4S,5R,6R,7aS)-2-methyl-4,5-bis(phenylmethoxy)-2,3,3a,4,5,6,7,7a-octahydro-1H-indol-6-ol;acetic acid
  参考文献：
  名称：

  Polyhydroxylated Indolines and Oxindoles from C-Glycosides via Sequential Henry Reaction, Michael Addition, and Reductive Amination/Amidation

  摘要：

  [GRAPHIC]6-Nitro-2'-carbonyl-C-glycofuranosides synthesized via Henry reaction from 1-C-allyl 5-aldo-C-glycoside underwent an intramolecular Michael addition to afford nitrocyclohexanol derivatives in good to excellent yield. Reduction of the nitro group followed by intramolecular amination with ketone and aldehyde and amidation with ester produced indoline and oxindole derivatives, respectively, in excellent yield.

  DOI：

  10.1021/jo070014o
• 作为产物：
  描述：

  1-C-allyl 2,3-di-O-benzyl-6-C-nitro-6-deoxy-α-D-ribo-hexano-furanoside 在 jones reagent 、 mercury(II) diacetate 、 potassium carbonate 作用下， 以 甲醇 、 水 、 丙酮 为溶剂， 反应 3.0h， 生成 (1S,2S,3R,4R,6S)-1-acetylmethyl-2,3-di-O-benzyl-4-hydroxy-6-nitrocyclohexane
  参考文献：
  名称：

  Polyhydroxylated Indolines and Oxindoles from C-Glycosides via Sequential Henry Reaction, Michael Addition, and Reductive Amination/Amidation

  摘要：

  [GRAPHIC]6-Nitro-2'-carbonyl-C-glycofuranosides synthesized via Henry reaction from 1-C-allyl 5-aldo-C-glycoside underwent an intramolecular Michael addition to afford nitrocyclohexanol derivatives in good to excellent yield. Reduction of the nitro group followed by intramolecular amination with ketone and aldehyde and amidation with ester produced indoline and oxindole derivatives, respectively, in excellent yield.

  DOI：

  10.1021/jo070014o