(2R,4S)-4-[[(2S)-2-(methoxymethyl)pyrrolidin-1-yl]methyl-dimethylsilyl]-4-phenylbutan-2-ol | 144787-81-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R,4S)-4-[[(2S)-2-(methoxymethyl)pyrrolidin-1-yl]methyl-dimethylsilyl]-4-phenylbutan-2-ol
• CAS: 144787-81-5
• 化学式: C₁₉H₃₃NO₂Si
• 分子量: 335.562
• InChiKey: IEKWUPJAQSEYGF-NEWSRXKRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.44
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  32.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,4S)-4-[[(2S)-2-(methoxymethyl)pyrrolidin-1-yl]methyl-dimethylsilyl]-4-phenylbutan-2-ol 在 potassium fluoride 、 双氧水 、 potassium hydrogencarbonate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 以75%的产率得到(1S,3R)-1-phenyl-1,3-butanediol
  参考文献：
  名称：

  Chiral organosilicon compounds in asymmetric synthesis of chiral 1,3-diols

  摘要：

  Chiral 1,3-diols can be prepared in high enantiomeric purity (>99% ee) from the reactions of the chiral silylcarbanion 2 with epoxides followed by oxidative cleavage of the carbon-silicon bond with hydrogen peroxide. The absolute configurations of some of the chiral 1,3-diols were determined by circular dichroism (CD).

  DOI：

  10.1021/jo00049a012
• 作为产物：
  描述：

  [(S)-2-(methoxymethyl)pyrrolidinomethyl]dimethyl benzylsilane 、 methyloxirane 在 仲丁基锂 作用下， 生成 (2S,4S)-4-[((S)-2-Methoxymethyl-pyrrolidin-1-ylmethyl)-dimethyl-silanyl]-4-phenyl-butan-2-ol 、 (2R,4S)-4-[[(2S)-2-(methoxymethyl)pyrrolidin-1-yl]methyl-dimethylsilyl]-4-phenylbutan-2-ol
  参考文献：
  名称：

  Chiral organosilicon compounds in asymmetric synthesis of chiral 1,3-diols

  摘要：

  Chiral 1,3-diols can be prepared in high enantiomeric purity (>99% ee) from the reactions of the chiral silylcarbanion 2 with epoxides followed by oxidative cleavage of the carbon-silicon bond with hydrogen peroxide. The absolute configurations of some of the chiral 1,3-diols were determined by circular dichroism (CD).

  DOI：

  10.1021/jo00049a012

文献信息

• Chiral organosilicon compounds in asymmetric synthesis of chiral 1,3-diols
  作者：T. H. Chan、K. T. Nwe

  DOI：10.1021/jo00049a012

  日期：1992.11

  Chiral 1,3-diols can be prepared in high enantiomeric purity (>99% ee) from the reactions of the chiral silylcarbanion 2 with epoxides followed by oxidative cleavage of the carbon-silicon bond with hydrogen peroxide. The absolute configurations of some of the chiral 1,3-diols were determined by circular dichroism (CD).