((3R,5S)-7-Oxo-3-phenyl-[1,4]oxazepan-5-yl)-acetic acid methyl ester | 871331-07-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧氮杂卓类
• 英文名称: ((3R,5S)-7-Oxo-3-phenyl-[1,4]oxazepan-5-yl)-acetic acid methyl ester
• 英文别名: methyl 2-[(3R,5S)-7-oxo-3-phenyl-1,4-oxazepan-5-yl]acetate
• CAS: 871331-07-6
• 化学式: C₁₄H₁₇NO₄
• 分子量: 263.293
• InChiKey: OKWDIFDEDOLMGW-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ((3R,5S)-7-Oxo-3-phenyl-[1,4]oxazepan-5-yl)-acetic acid methyl ester 在 palladium dihydroxide 氢气 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以96%的产率得到(R)-3-Amino-4-methoxycarbonylbutyric acid
  参考文献：
  名称：

  Enantioselective synthesis of β-amino-diacids

  摘要：

  An efficient route to orthogonally protected beta-amino-diacids is described: chiral derivative 3 was shown to be a precursor of enantiopure substituted beta-amino acids. The key step of the procedure is a diastereoselective reduction of beta-enaminolactones 5 by NaBH3CN in CH2Cl2. A study concerning the regio- and diastereoselectivity of alkylation of beta-enarninolactone 3 is also presented. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.09.114
• 作为产物：
  描述：

  methyl 2-[(3R)-7-oxo-3-phenyl-3,4-dihydro-2H-1,4-oxazepin-5-yl]acetate 在 溶剂黄146 、 sodium cyanoborohydride 、 氯化铵 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 1.0h， 以53%的产率得到((3R,5S)-7-Oxo-3-phenyl-[1,4]oxazepan-5-yl)-acetic acid methyl ester
  参考文献：
  名称：

  Enantioselective synthesis of β-amino-diacids

  摘要：

  An efficient route to orthogonally protected beta-amino-diacids is described: chiral derivative 3 was shown to be a precursor of enantiopure substituted beta-amino acids. The key step of the procedure is a diastereoselective reduction of beta-enaminolactones 5 by NaBH3CN in CH2Cl2. A study concerning the regio- and diastereoselectivity of alkylation of beta-enarninolactone 3 is also presented. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.09.114

文献信息

• Enantioselective synthesis of β-amino-diacids
  作者：Jeanne Alladoum、Luc Dechoux

  DOI：10.1016/j.tetlet.2005.09.114

  日期：2005.11

  An efficient route to orthogonally protected beta-amino-diacids is described: chiral derivative 3 was shown to be a precursor of enantiopure substituted beta-amino acids. The key step of the procedure is a diastereoselective reduction of beta-enaminolactones 5 by NaBH3CN in CH2Cl2. A study concerning the regio- and diastereoselectivity of alkylation of beta-enarninolactone 3 is also presented. (c) 2005 Elsevier Ltd. All rights reserved.