3-[(1S,6R)-3,4-Dimethyl-6-((1R,2R,3R,4R)-1,2,3,4,5-pentaacetoxy-pentyl)-cyclohex-3-enyl]-propionic acid methyl ester | 374592-17-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-[(1S,6R)-3,4-Dimethyl-6-((1R,2R,3R,4R)-1,2,3,4,5-pentaacetoxy-pentyl)-cyclohex-3-enyl]-propionic acid methyl ester
• CAS: 374592-17-3
• 化学式: C₂₇H₄₀O₁₂
• 分子量: 556.607
• InChiKey: NZBJKSKYPPQMNY-UQSTXUIISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.59
• 重原子数：
  39.0
• 可旋转键数：
  13.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  157.8
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  3-[(1S,6R)-3,4-Dimethyl-6-((1R,2R,3R,4R)-1,2,3,4,5-pentaacetoxy-pentyl)-cyclohex-3-enyl]-propionic acid methyl ester 在 sodium periodate 、 sodium methylate 作用下， 生成 3-((1S,6R)-6-Formyl-3,4-dimethyl-cyclohex-3-enyl)-propionic acid methyl ester
  参考文献：
  名称：

  Stereoselective denitrohydrogenation reactions of 4-alkyl-5-glyco-4-nitrocyclohex-1-enes

  摘要：

  The denitrohydrogenation of chiral 4-alkyl-5-glyco-4-nitrocyclohex-1-enes (1 and 3) with tri-n-butyltin hydride and azobisisobutironitrile proceeded in a completely stereoselective way. In each case. the hydrogen atom provided by tri-n-butyltin hydride adds to a free radical intermediate in a trans mode to the adjacent, sterically demanding, sugar side-chain. Attempts to perform denitroalkylation reactions of 1a, 3a or 8 with electron-deficient alkenes yielded only denitrohydrogenated products. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00304-4
• 作为产物：
  描述：

  1',2',3',4',5'-penta-O-acetyl-1'-C-[(4S,5R)-1,2-dimethyl-4-(2''-methoxycarbonylethyl)-4-nitrocyclohex-1-en-5-yl]-D-manno-pentitol 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 反应 2.0h， 以40%的产率得到3-[(1S,6R)-3,4-Dimethyl-6-((1R,2R,3R,4R)-1,2,3,4,5-pentaacetoxy-pentyl)-cyclohex-3-enyl]-propionic acid methyl ester
  参考文献：
  名称：

  Stereoselective denitrohydrogenation reactions of 4-alkyl-5-glyco-4-nitrocyclohex-1-enes

  摘要：

  The denitrohydrogenation of chiral 4-alkyl-5-glyco-4-nitrocyclohex-1-enes (1 and 3) with tri-n-butyltin hydride and azobisisobutironitrile proceeded in a completely stereoselective way. In each case. the hydrogen atom provided by tri-n-butyltin hydride adds to a free radical intermediate in a trans mode to the adjacent, sterically demanding, sugar side-chain. Attempts to perform denitroalkylation reactions of 1a, 3a or 8 with electron-deficient alkenes yielded only denitrohydrogenated products. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00304-4