methyl (+/-)-(2E)-5-(bromoacetoxy)-4-phenyl-2-pentenoate | 173423-62-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl (+/-)-(2E)-5-(bromoacetoxy)-4-phenyl-2-pentenoate
• 英文别名: methyl (E)-5-(2-bromoacetyl)oxy-4-phenylpent-2-enoate
• CAS: 173423-62-6
• 化学式: C₁₄H₁₅BrO₄
• 分子量: 327.175
• InChiKey: WOOPSUNJIMDKRI-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (+/-)-(2E)-5-(bromoacetoxy)-4-phenyl-2-pentenoate 在 高氯酸铵 、 (1,4,8,11-tetraazacyclotetradecane)nickel(II) perchlorate 、 高氯酸四乙基铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以46%的产率得到methyl (2E)-5-acetoxy-4-phenyl-2-pentenoate
  参考文献：
  名称：

  Synthesis of Six-Membered Compounds by Environmentally Friendly Cyclization Using Indirect Electrolysis

  摘要：

  [Ni(cyclam)](ClO4)(2)-catalyzed indirect electroreduction of olefinic bromides produced six-membered compounds in low to high yields. The synthetic intermediate 49 of Ipecac and Corynanthe alkaloids was obtained in 88% yield in a highly stereoselective manner. Lactam 66, the synthetic precursor of tacamonine, was prepared in 49% yield as a mixture of two diastereoisomers. The electrolysis of the bromoacetates gave the debrominated compounds in good yields.

  DOI：

  10.1021/jo951653e
• 作为产物：
  描述：

  2-苯基-1,3-丙二醇 在 4-二甲氨基吡啶 、 重铬酸吡啶 、 4 A molecular sieve 、 水 、 sodium hydride 、 溶剂黄146 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 63.5h， 生成 methyl (+/-)-(2E)-5-(bromoacetoxy)-4-phenyl-2-pentenoate
  参考文献：
  名称：

  Synthesis of Six-Membered Compounds by Environmentally Friendly Cyclization Using Indirect Electrolysis

  摘要：

  [Ni(cyclam)](ClO4)(2)-catalyzed indirect electroreduction of olefinic bromides produced six-membered compounds in low to high yields. The synthetic intermediate 49 of Ipecac and Corynanthe alkaloids was obtained in 88% yield in a highly stereoselective manner. Lactam 66, the synthetic precursor of tacamonine, was prepared in 49% yield as a mixture of two diastereoisomers. The electrolysis of the bromoacetates gave the debrominated compounds in good yields.

  DOI：

  10.1021/jo951653e

文献信息

• Synthesis of Six-Membered Compounds by Environmentally Friendly Cyclization Using Indirect Electrolysis
  作者：Masataka Ihara、Akira Katsumata、Fumihito Setsu、Yuji Tokunaga、Keiichiro Fukumoto

  DOI：10.1021/jo951653e

  日期：1996.1.1

  [Ni(cyclam)](ClO4)(2)-catalyzed indirect electroreduction of olefinic bromides produced six-membered compounds in low to high yields. The synthetic intermediate 49 of Ipecac and Corynanthe alkaloids was obtained in 88% yield in a highly stereoselective manner. Lactam 66, the synthetic precursor of tacamonine, was prepared in 49% yield as a mixture of two diastereoisomers. The electrolysis of the bromoacetates gave the debrominated compounds in good yields.