(1R,3S,4R,5S,6R)-6-(2-furyl)-5-(methyoxymethyl)-4-methyl-1,3-cycloheptanediol | 149129-90-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,3S,4R,5S,6R)-6-(2-furyl)-5-(methyoxymethyl)-4-methyl-1,3-cycloheptanediol
• 英文别名: (1R,3S,4R,5S,6R)-6-(furan-2-yl)-5-(methoxymethyl)-4-methylcycloheptane-1,3-diol
• CAS: 149129-90-8
• 化学式: C₁₄H₂₂O₄
• 分子量: 254.326
• InChiKey: JUZXNJOXLBRINS-KVSVUVNWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  62.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-溴苯甲酰氯 、 (1R,3S,4R,5S,6R)-6-(2-furyl)-5-(methyoxymethyl)-4-methyl-1,3-cycloheptanediol 在 4-二甲氨基吡啶 作用下， 反应 13.0h， 生成 (1R,3S,4R,5S,6R)-1,3-bis((p-bromobenzoyl)oxy)-6-(2-furyl)-5-(methoxymethyl)-4-methylcycloheptane
  参考文献：
  名称：

  Stereoselective Synthesis of Seven-Membered Carbocycles from 2-Amino-1,3-butadienes and Vinyl Chromium Fischer-Type Carbenes

  摘要：

  Seven-membered ring carbocycles are prepared by reaction of easily avaliable 2-amino-1,3-butadienes with vinyl Fischer carbenes. Hydrolysis of the cycloadduct initially formed gives rise to cyclohepta-1,3-diones with total regio- and stereoselectivity in a one-pot process. When 2-aminobutadienes bearing a prolinol derivative as a chiral auxiliary are used, the corresponding cyclic diketones are obtained with very high enantiomeric excesses. The absolute configuration of the stereogenic centers generated was determined with the aid of ROESY and CD measurements.

  DOI：

  10.1021/ja00142a006
• 作为产物：
  描述：

  (E)-N-(2-methyl-1-methylene-4-methoxy-2-butenyl)-2-(S)-methoxymethylpyrrolidine 在 盐酸 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 32.0h， 生成 (1R,3S,4R,5S,6R)-6-(2-furyl)-5-(methyoxymethyl)-4-methyl-1,3-cycloheptanediol
  参考文献：
  名称：

  Stereoselective Synthesis of Seven-Membered Carbocycles from 2-Amino-1,3-butadienes and Vinyl Chromium Fischer-Type Carbenes

  摘要：

  Seven-membered ring carbocycles are prepared by reaction of easily avaliable 2-amino-1,3-butadienes with vinyl Fischer carbenes. Hydrolysis of the cycloadduct initially formed gives rise to cyclohepta-1,3-diones with total regio- and stereoselectivity in a one-pot process. When 2-aminobutadienes bearing a prolinol derivative as a chiral auxiliary are used, the corresponding cyclic diketones are obtained with very high enantiomeric excesses. The absolute configuration of the stereogenic centers generated was determined with the aid of ROESY and CD measurements.

  DOI：

  10.1021/ja00142a006