(+/-)-tert-Butyl (E)-3-((2-(bromomethyl)butoxy)carbonyl)prop-2-enoate | 157405-04-4

• 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: (+/-)-tert-Butyl (E)-3-((2-(bromomethyl)butoxy)carbonyl)prop-2-enoate
• 英文别名: 1-O-[2-(bromomethyl)butyl] 4-O-tert-butyl (E)-but-2-enedioate
• CAS: 157405-04-4
• 化学式: C₁₃H₂₁BrO₄
• 分子量: 321.211
• InChiKey: LIIOSKUZIWAFFQ-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.69
• 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：

  (+/-)-tert-Butyl (E)-3-((2-(bromomethyl)butoxy)carbonyl)prop-2-enoate 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 、 苯 为溶剂， 反应 10.0h， 生成 (+/-)-tert-Butyl 3-carbamoyl>-5-(hydroxymethyl)heptanoate
  参考文献：
  名称：

  Asymmetric Total Synthesis of Tacamonine (Pseudovincamone I) via Radical Cyclization

  摘要：

  The radical cyclizations of (+/-)-(E)-3-((2-(bromomethyl)butoxy)carbonyl)prop-2-enoates 11 and 12 and (+/-)-ethyl (E)-3-{N-[2-(bromomethyl)butyl]-N-[2-(3-indolyl)ethyl]carbamoyl} prop-2-enoate (25) were carried out with (TMS)(3)SiH or Bu(3)SnH in the presence of AIBN. (-)-(2S)-2-((tert-Butyldimethylsilyloxy)methyl)butan-1-ol (6), which was prepared by two different methods, was converted into (+)-25. The radical cyclization of(+)-25 produced piperidinone 18 as a diastereomeric mixture, which was transformed into tacamonine (1).

  DOI：

  10.1021/jo00097a037
• 作为产物：
  描述：

  2-乙基-1,3-丙二醇 在 4-二甲氨基吡啶 、 lithium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 对甲苯磺酸 、 N,N'-二环己基碳二亚胺 、 barium carbonate 作用下， 以 甲醇 、 四氯化碳 、 二氯甲烷 、 水 、 苯 为溶剂， 反应 11.0h， 生成 (+/-)-tert-Butyl (E)-3-((2-(bromomethyl)butoxy)carbonyl)prop-2-enoate
  参考文献：
  名称：

  Asymmetric Total Synthesis of Tacamonine (Pseudovincamone I) via Radical Cyclization

  摘要：

  The radical cyclizations of (+/-)-(E)-3-((2-(bromomethyl)butoxy)carbonyl)prop-2-enoates 11 and 12 and (+/-)-ethyl (E)-3-{N-[2-(bromomethyl)butyl]-N-[2-(3-indolyl)ethyl]carbamoyl} prop-2-enoate (25) were carried out with (TMS)(3)SiH or Bu(3)SnH in the presence of AIBN. (-)-(2S)-2-((tert-Butyldimethylsilyloxy)methyl)butan-1-ol (6), which was prepared by two different methods, was converted into (+)-25. The radical cyclization of(+)-25 produced piperidinone 18 as a diastereomeric mixture, which was transformed into tacamonine (1).

  DOI：

  10.1021/jo00097a037

文献信息

• Asymmetric Total Synthesis of Tacamonine (Pseudovincamone I) via Radical Cyclization
  作者：Masataka Ihara、Fumihito Setsu、Miyuki Shohda、Nobuaki Taniguchi、Yuji Tokunaga、Keiichiro Fukumoto

  DOI：10.1021/jo00097a037

  日期：1994.9

  The radical cyclizations of (+/-)-(E)-3-((2-(bromomethyl)butoxy)carbonyl)prop-2-enoates 11 and 12 and (+/-)-ethyl (E)-3-N-[2-(bromomethyl)butyl]-N-[2-(3-indolyl)ethyl]carbamoyl} prop-2-enoate (25) were carried out with (TMS)(3)SiH or Bu(3)SnH in the presence of AIBN. (-)-(2S)-2-((tert-Butyldimethylsilyloxy)methyl)butan-1-ol (6), which was prepared by two different methods, was converted into (+)-25. The radical cyclization of(+)-25 produced piperidinone 18 as a diastereomeric mixture, which was transformed into tacamonine (1).