(2R)-2-(N-benzyloxycarbonylamino)octan-4-one | 874141-32-9

• 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: (2R)-2-(N-benzyloxycarbonylamino)octan-4-one
• 英文别名: benzyl N-[(2R)-4-oxooctan-2-yl]carbamate
• CAS: 874141-32-9
• 化学式: C₁₆H₂₃NO₃
• 分子量: 277.364
• InChiKey: IHXOLLHICDFNFY-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R)-2-(N-benzyloxycarbonylamino)octan-4-one 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'R)-2-butyl-2-(2'-amino-propyl)-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-(N-benzyloxycarbonylamino)-(N'-methoxy-N'-methylbutananamide) 、 正丁基氯化镁 以 1,4-二氧六环 、 乙醚 、 四氢呋喃 为溶剂， 反应 0.75h， 生成 (2R)-2-(N-benzyloxycarbonylamino)octan-4-one
  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

文献信息

• Asymmetric synthesis of 1,3-aminoketals
  作者：Annabelle Bariau、Jean-Louis Canet、Pierre Chalard、Yves Troin

  DOI：10.1016/j.tetasy.2005.09.024

  日期：2005.11

  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.