(-)-ethyl (2E)-4-<((2'R)-2'-(bromomethyl)butanoyl)oxy>-2-butenoate | 163457-28-1

• 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: (-)-ethyl (2E)-4-<((2'R)-2'-(bromomethyl)butanoyl)oxy>-2-butenoate
• 英文别名: [(E)-4-ethoxy-4-oxobut-2-enyl] (2S)-2-(bromomethyl)butanoate
• CAS: 163457-28-1
• 化学式: C₁₁H₁₇BrO₄
• 分子量: 293.158
• InChiKey: PFFBUBHZBNBSOO-VUHVRTRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 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：

  (-)-ethyl (2E)-4-<((2'R)-2'-(bromomethyl)butanoyl)oxy>-2-butenoate 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39%的产率得到(-)-(2R)-ethyl-4-<(ethoxycarbonyl)methyl>-5-pentanolide
  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：

  (+)-(4S)-3-<(2'R)-2'-(hydroxymethyl)butanoyl>-4-benzyl-2-oxazolidinone 在 4-二甲氨基吡啶 、 lithium hydroxide 、 四溴化碳 、 水 、 双氧水 、 溶剂黄146 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 34.5h， 生成 (-)-ethyl (2E)-4-<((2'R)-2'-(bromomethyl)butanoyl)oxy>-2-butenoate
  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

• Indirect Electroreductive Cyclization for Syntheses of Key Intermediates of Several Indole and Ipecac Alkaloids.
  作者：Masataka IHARA、Fumihito SETSU、Yuji TOKUNAGA、Keiichiro FUKUMOTO、Yoshitomo KASHIWAGI、Tetsuo OSA

  DOI：10.1248/cpb.43.362

  日期：——

  Indirect electroreductive cyclization of η-bromo-α, β-unsaturated esters 1-6 using Co(III) or Ni(II)complex as an electron-transfer catalyst provided the six membered compounds 7-12, which are useful synthetic intermediates of several indole and ipecac alkaloids.

  使用 Co（III）或 Ni（II）络合物作为电子转移催化剂，对 η-溴-α，β-不饱和酯 1-6 进行间接电还原环化，得到了六位化合物 7-12，它们是几种吲哚和开环十四烷生物碱的有用合成中间体。
• 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.