Carbamic acid,[(1S)-1-(3,4-dimethoxyphenyl)-2-(2-methyl-1,3-dioxolan-2-yl)ethyl]-,phenylmethyl ester | 874141-40-9

• 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: Carbamic acid,[(1S)-1-(3,4-dimethoxyphenyl)-2-(2-methyl-1,3-dioxolan-2-yl)ethyl]-,phenylmethyl ester
• 英文别名: (+)-(2'S)-2-[2'-(N-benzyloxycarbonylamino)-2'-(3,4-dimethoxypentyl)-ethyl]-2-methyl-1,3-dioxolane
• CAS: 874141-40-9
• 化学式: C₂₂H₂₇NO₆
• 分子量: 401.459
• InChiKey: ILLJSMNTCUFRMQ-SFHVURJKSA-N

物化性质

• 熔点：
  88.0 °C
• 沸点：
  552.1±50.0 °C(Predicted)
• 密度：
  1.172±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.82
• 重原子数：
  29.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  75.25
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  Carbamic acid,[(1S)-1-(3,4-dimethoxyphenyl)-2-(2-methyl-1,3-dioxolan-2-yl)ethyl]-,phenylmethyl ester 在 palladium on activated charcoal ammonium formate 作用下， 以 甲醇 为溶剂， 反应 5.0h， 生成 (-)-(2'S)-2-[2'-amino-2'-(3,4-dimethoxypentyl)ethyl]-2-methyl-1,3-dioxolane
  参考文献：
  名称：

  Asymmetric synthesis of 1,3-aminoketals

  摘要：

  The asymmetric synthesis of alpha-chiral 1,3-aminoketals 1, useful chiral building blocks for piperidine preparation, was achieved in seven steps involving highly diastereoselective 1,4-addition of Davies' lithium amide to an alpha,beta-unsaturated ester. Problems of partial racernization observed during transformation of the ester moiety into a keto function, via a Weinreb amide, were solved using non-conventional experimental conditions. This procedure allowed the preparation of the title compounds in > 90% enantiomeric excess. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.09.024
• 作为产物：
  描述：

  (-)-(3S)-3-(N-benzyloxycarbonylamino)-3-(3,4-dimethoxyphenyl)-(N'-methoxy-N'-methylpropanamide) 在 对甲苯磺酸 、 原甲酸三甲酯 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醚 为溶剂， 反应 0.75h， 生成 Carbamic acid,[(1S)-1-(3,4-dimethoxyphenyl)-2-(2-methyl-1,3-dioxolan-2-yl)ethyl]-,phenylmethyl ester
  参考文献：
  名称：

  Asymmetric synthesis of 1,3-aminoketals

  摘要：

  The asymmetric synthesis of alpha-chiral 1,3-aminoketals 1, useful chiral building blocks for piperidine preparation, was achieved in seven steps involving highly diastereoselective 1,4-addition of Davies' lithium amide to an alpha,beta-unsaturated ester. Problems of partial racernization observed during transformation of the ester moiety into a keto function, via a Weinreb amide, were solved using non-conventional experimental conditions. This procedure allowed the preparation of the title compounds in > 90% enantiomeric excess. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.09.024