(2S,4Z)-2-[(1R,2R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]cyclopropyl]-3,6,7,8-tetrahydro-2H-oxonin-9-one | 201337-69-1

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (2S,4Z)-2-[(1R,2R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]cyclopropyl]-3,6,7,8-tetrahydro-2H-oxonin-9-one
• CAS: 201337-69-1
• 化学式: C₁₈H₃₂O₃Si
• 分子量: 324.536
• InChiKey: MJXWBERWFOVCFU-WYPWVBMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.69
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,4Z)-2-[(1R,2R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]cyclopropyl]-3,6,7,8-tetrahydro-2H-oxonin-9-one 在 四丁基氟化铵 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 8.5h， 生成 (1R,2R,2'S,Z)-2-(9'-oxo-2',3',6',7',8',9'-hexahydrooxonin-2'-yl)cyclopropanecarbaldehyde
  参考文献：
  名称：

  Stereoselective Synthesis of a Key Precursor of Halicholactone and Neohalicholactone

  摘要：

  An efficient synthesis of a known precursor of halicholactone (1a) and neohalicholactone (1b) has been developed using the strategically functionalized key cyclopropane intermediate 2, which in turn has been synthesized via stereoselective cyclopropanation of trans-cinnamyl alcohol in the presence of the chiral dioxaborolane ligand 4. Elaboration of the above bifunctional cyclopropane to the target molecule was achieved in a relatively short reaction sequence and in good overall yield, representing a formal synthesis of the title compounds.

  DOI：

  10.1021/jo971564x
• 作为产物：
  描述：

  4-羧丁基三苯基溴化膦 在 4-二甲氨基吡啶 、 2,4,6-三氯苯甲酰氯 、 sodium hexamethyldisilazane 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 生成 (2S,4Z)-2-[(1R,2R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]cyclopropyl]-3,6,7,8-tetrahydro-2H-oxonin-9-one
  参考文献：
  名称：

  Stereoselective Synthesis of a Key Precursor of Halicholactone and Neohalicholactone

  摘要：

  An efficient synthesis of a known precursor of halicholactone (1a) and neohalicholactone (1b) has been developed using the strategically functionalized key cyclopropane intermediate 2, which in turn has been synthesized via stereoselective cyclopropanation of trans-cinnamyl alcohol in the presence of the chiral dioxaborolane ligand 4. Elaboration of the above bifunctional cyclopropane to the target molecule was achieved in a relatively short reaction sequence and in good overall yield, representing a formal synthesis of the title compounds.

  DOI：

  10.1021/jo971564x