(3S)-3-[(1R,2R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]cyclopropyl]-3-hydroxypropanal | 201337-67-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3S)-3-[(1R,2R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]cyclopropyl]-3-hydroxypropanal
• CAS: 201337-67-9
• 化学式: C₁₃H₂₆O₃Si
• 分子量: 258.433
• InChiKey: VCIPMEUXGHTMEP-TUAOUCFPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.59
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S)-3-[(1R,2R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]cyclopropyl]-3-hydroxypropanal 在 4-二甲氨基吡啶 、 2,4,6-三氯苯甲酰氯 、 四丁基氟化铵 、 sodium hexamethyldisilazane 、 三乙胺 、 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 24.5h， 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：

  1-[(1R,2R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-cyclopropyl]-but-3-en-1-one 在 sodium periodate 、 四氧化锇 、 N-甲基吲哚酮 、 sodium methylate 、 碳酸氢钠 、 potassium tri-sec-butyl-borohydride 、 溶剂黄146 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 水 、 丙酮 、 甲苯 为溶剂， 反应 12.0h， 生成 (3S)-3-[(1R,2R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]cyclopropyl]-3-hydroxypropanal
  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

文献信息

• Stereoselective Synthesis of a Key Precursor of Halicholactone and Neohalicholactone
  作者：Debendra K. Mohapatra、Apurba Datta

  DOI：10.1021/jo971564x

  日期：1998.2.1

  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.