Methyl 2-[(2-cyano-1-phenylprop-2-enyl)amino]acetate | 1141875-56-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Methyl 2-[(2-cyano-1-phenylprop-2-enyl)amino]acetate
• 英文别名: methyl 2-[(2-cyano-1-phenylprop-2-enyl)amino]acetate
• CAS: 1141875-56-0
• 化学式: C₁₃H₁₄N₂O₂
• 分子量: 230.266
• InChiKey: SSQRNXQBEOYDJE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  62.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Methyl 2-[(2-cyano-1-phenylprop-2-enyl)amino]acetate 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以84%的产率得到2-Oxo-5-phenyl-1,4-oxazepane-6-carbonitrile
  参考文献：
  名称：

  A concise α-amino acid-based synthetic approach to [1,4]oxazepin-2-ones from Baylis–Hillman adducts

  摘要：

  An original two-step process for the synthesis of [1,4]oxazepin-2-ones starting from Baylis-Hillman (BH) adducts is reported. The protocol involves a nucleophilic substitution of the acetates of BH adducts with renewable natural alpha-amino esters followed by base-catalyzed intramolecular Michael addition. These sequential reactions are operationally simple, performed under ambient conditions, and give 81-93% yields of the target [1,4]oxazepin-2-ones. Thus, the present invention opens up a new aspect for the synthetic utility of BH adducts. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.01.048
• 作为产物：
  描述：

  甘氨酸甲酯盐酸盐 、 3-acetoxy-2-methylene-3-phenylpropionitrile 在 三乙烯二胺 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 Methyl 2-[(2-cyano-1-phenylprop-2-enyl)amino]acetate
  参考文献：
  名称：

  A concise α-amino acid-based synthetic approach to [1,4]oxazepin-2-ones from Baylis–Hillman adducts

  摘要：

  An original two-step process for the synthesis of [1,4]oxazepin-2-ones starting from Baylis-Hillman (BH) adducts is reported. The protocol involves a nucleophilic substitution of the acetates of BH adducts with renewable natural alpha-amino esters followed by base-catalyzed intramolecular Michael addition. These sequential reactions are operationally simple, performed under ambient conditions, and give 81-93% yields of the target [1,4]oxazepin-2-ones. Thus, the present invention opens up a new aspect for the synthetic utility of BH adducts. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.01.048

文献信息

• A concise α-amino acid-based synthetic approach to [1,4]oxazepin-2-ones from Baylis–Hillman adducts
  作者：Lal Dhar S. Yadav、Vishnu P. Srivastava、Rajesh Patel

  DOI：10.1016/j.tetlet.2009.01.048

  日期：2009.4

  An original two-step process for the synthesis of [1,4]oxazepin-2-ones starting from Baylis-Hillman (BH) adducts is reported. The protocol involves a nucleophilic substitution of the acetates of BH adducts with renewable natural alpha-amino esters followed by base-catalyzed intramolecular Michael addition. These sequential reactions are operationally simple, performed under ambient conditions, and give 81-93% yields of the target [1,4]oxazepin-2-ones. Thus, the present invention opens up a new aspect for the synthetic utility of BH adducts. (C) 2009 Elsevier Ltd. All rights reserved.