Carbamic acid, [(1S)-1-(3,4-dimethoxyphenyl)-3-oxobutyl]-,phenylmethyl ester | 874141-34-1

• 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)-3-oxobutyl]-,phenylmethyl ester
• 英文别名: (4S)-4-(N-benzyloxycarbonylamino)-4-(3,4-dimethoxyphenyl)butan-2-one
• CAS: 874141-34-1
• 化学式: C₂₀H₂₃NO₅
• 分子量: 357.406
• InChiKey: VLXSZMFYQAAJEA-KRWDZBQOSA-N

物化性质

• 沸点：
  532.3±50.0 °C(Predicted)
• 密度：
  1.163±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.65
• 重原子数：
  26.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  73.86
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  Carbamic acid, [(1S)-1-(3,4-dimethoxyphenyl)-3-oxobutyl]-,phenylmethyl ester 在 palladium on activated charcoal ammonium formate 、 对甲苯磺酸 、 原甲酸三甲酯 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：

  (-)-(3R)-3-amino-3-(3,4-dimethoxyphenyl)-(N-methoxy-N-methylpropananamide) 在 sodium carbonate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 3.75h， 生成 Carbamic acid, [(1S)-1-(3,4-dimethoxyphenyl)-3-oxobutyl]-,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