Methyl 4-bromo-4-(bromomethyl)-5-oxohexanoate | 199176-98-2

• 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 4-bromo-4-(bromomethyl)-5-oxohexanoate
• CAS: 199176-98-2
• 化学式: C₈H₁₂Br₂O₃
• 分子量: 315.989
• InChiKey: XTYQMIXPMRMXGT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Methyl 4-bromo-4-(bromomethyl)-5-oxohexanoate 在 palladium on activated charcoal tetraphosphorus decasulfide 、 四丁基氯化铵 、 氢气 、 镍 、 对甲苯磺酸 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 六甲基磷酰三胺 、 水 、 溶剂黄146 、 甲苯 、 xylene 为溶剂， 反应 65.0h， 生成 (+/-)-minovincine
  参考文献：
  名称：

  Synthesis of Vinca Alkaloids and Related Compounds. 90.¹ New Results in the Synthesis of Alkaloids with the Aspidospermane Skeleton. First Total Synthesis of (±)-3-Oxominovincine

  摘要：

  The tryptamine derivative 1 readily reacted with methyl 4-acetyl-5-bromopent-4-enoate (9) that had been built up from 2,4-pentanedione. On intramolecular dehydration and subsequent [4 + 2] cycloaddition, the reaction product 10 gave the epimers 12 and 13 having the D-secoaspidospermane skeleton. Compound 12 directly and 13 after epimerization yielded (+/-)-3-oxominovincine (14). Regioselective reduction of 14 furnished (+)-minovincine (17).

  DOI：

  10.1021/jo9713464
• 作为产物：
  描述：

  4-乙酰基-5-羰基己酸甲酯 在 溴 、 potassium carbonate 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 13.0h， 生成 Methyl 4-bromo-4-(bromomethyl)-5-oxohexanoate
  参考文献：
  名称：

  Synthesis of Vinca Alkaloids and Related Compounds. 90.¹ New Results in the Synthesis of Alkaloids with the Aspidospermane Skeleton. First Total Synthesis of (±)-3-Oxominovincine

  摘要：

  The tryptamine derivative 1 readily reacted with methyl 4-acetyl-5-bromopent-4-enoate (9) that had been built up from 2,4-pentanedione. On intramolecular dehydration and subsequent [4 + 2] cycloaddition, the reaction product 10 gave the epimers 12 and 13 having the D-secoaspidospermane skeleton. Compound 12 directly and 13 after epimerization yielded (+/-)-3-oxominovincine (14). Regioselective reduction of 14 furnished (+)-minovincine (17).

  DOI：

  10.1021/jo9713464

文献信息

• Synthesis of Vinca Alkaloids and Related Compounds. 90.¹ New Results in the Synthesis of Alkaloids with the Aspidospermane Skeleton. First Total Synthesis of (±)-3-Oxominovincine
  作者：György Kalaus、Imre Juhász、István Greiner、Mária Kajtár-Peredy、János Brlik、Lajos Szabó、Csaba Szántay

  DOI：10.1021/jo9713464

  日期：1997.12.1

  The tryptamine derivative 1 readily reacted with methyl 4-acetyl-5-bromopent-4-enoate (9) that had been built up from 2,4-pentanedione. On intramolecular dehydration and subsequent [4 + 2] cycloaddition, the reaction product 10 gave the epimers 12 and 13 having the D-secoaspidospermane skeleton. Compound 12 directly and 13 after epimerization yielded (+/-)-3-oxominovincine (14). Regioselective reduction of 14 furnished (+)-minovincine (17).