methyl (3-exo)-9-oxobicyclo[3.3.1]nonane-3-carboxylate | 22262-62-0

• 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: methyl (3-exo)-9-oxobicyclo[3.3.1]nonane-3-carboxylate
• 英文别名: 3-Exo-carbomethoxy-bicyclo<3.3.1>nonan
• CAS: 22262-62-0
• 化学式: C₁₁H₁₆O₃
• 分子量: 196.246
• InChiKey: LPOQWKGXUZCSIW-AYMMMOKOSA-N

物化性质

• 沸点：
  289.9±33.0 °C(Predicted)
• 密度：
  1.122±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.55
• 重原子数：
  14.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  methyl (3-exo)-9-oxobicyclo[3.3.1]nonane-3-carboxylate 在 氢气 、 镍 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 8.0h， 生成 (1R,3S,5S,9S)-9-Amino-bicyclo[3.3.1]nonane-3-carboxylic acid methyl ester
  参考文献：
  名称：

  A Highly Efficient Synthesis of Potent and Selective Butyrolactam Inhibitors of 11β-Hsd1

  摘要：

  A convergent synthesis of structurally novel butyrolactam 11 beta-HSD1 inhibitors is described. The approach features an efficient Ireland-Claisen reaction to construct a highly substituted aldehyde building block which is converted to a lactam via a tandem reductive amination/cyclization sequence. The generality of the synthetic sequence is demonstrated during the preparation of two additional potent 11 beta-HSD1 inhibitors.

  DOI：

  10.1021/ol061429j
• 作为产物：
  描述：

  9-oxo-bicyclo[3.3.1]nonane-3-carboxylic acid methyl ester 在 Amberlyst 15 、 sodium methylate 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 13.0h， 生成 methyl (3-exo)-9-oxobicyclo[3.3.1]nonane-3-carboxylate
  参考文献：
  名称：

  A Highly Efficient Synthesis of Potent and Selective Butyrolactam Inhibitors of 11β-Hsd1

  摘要：

  A convergent synthesis of structurally novel butyrolactam 11 beta-HSD1 inhibitors is described. The approach features an efficient Ireland-Claisen reaction to construct a highly substituted aldehyde building block which is converted to a lactam via a tandem reductive amination/cyclization sequence. The generality of the synthetic sequence is demonstrated during the preparation of two additional potent 11 beta-HSD1 inhibitors.

  DOI：

  10.1021/ol061429j

文献信息

• Experimental evidence for a synperiplanar stereoelectronic effect in the ozonolysis of a tricyclic acetal
  作者：Shigui Li、Pierre Deslongchamps

  DOI：10.1016/s0040-4039(00)61559-9

  日期：1993.11

  Tricyclic acetal 1 in which the ring oxygen has one electron pair synperiplanar to the CH bond is easily oxidized with ozone.

  三环缩醛1中的环氧具有一个相对于CH键在平面上的电子对，很容易被臭氧氧化。
• .alpha., .alpha.' Annelation of cyclic ketones. Synthesis and conformational properties of bicyclo[3.3.1]nonanone derivatives
  作者：John M. McEuen、Roger Peter Nelson、Richard G. Lawton

  DOI：10.1021/jo00828a032

  日期：1970.3
• WO2008/77556
  申请人：——

  公开号：——

  公开（公告）日：——