(+/-)-4-ethyl-2-<(ethoxycarbonyl)methyl>-5-pentanolide | 157405-05-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (+/-)-4-ethyl-2-<(ethoxycarbonyl)methyl>-5-pentanolide
• 英文别名: (+/-)-4-Ethyl-2-((ethoxycarbonyl)methyl)-5-pentanolide；Ethyl 2-(5-ethyl-2-oxooxan-3-yl)acetate；ethyl 2-(5-ethyl-2-oxooxan-3-yl)acetate
• CAS: 157405-05-5
• 化学式: C₁₁H₁₈O₄
• 分子量: 214.262
• InChiKey: OEHGULVFQZKSIQ-UHFFFAOYSA-N

物化性质

• 沸点：
  326.5±15.0 °C(predicted)
• 密度：
  1.041±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 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：

  色胺 、 (+/-)-4-ethyl-2-<(ethoxycarbonyl)methyl>-5-pentanolide 在 三甲基铝 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 3.0h， 以25%的产率得到(+/-)-Ethyl 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) 、 偶氮二异丁腈 、 水 、 三正丁基氢锡 、 对甲苯磺酸 、 N,N'-二环己基碳二亚胺 、 barium carbonate 作用下， 以 苯 为溶剂， 反应 5.0h， 生成 (+/-)-4-ethyl-2-<(ethoxycarbonyl)methyl>-5-pentanolide
  参考文献：
  名称：

  Ihara, Masataka; Setsu, Fumihito; Shohda, Miyuki, Heterocycles, 1994, vol. 37, # 1, p. 289 - 292

  摘要：

  DOI：

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.
• Ihara, Masataka; Setsu, Fumihito; Shohda, Miyuki, Heterocycles, 1994, vol. 37, # 1, p. 289 - 292
  作者：Ihara, Masataka、Setsu, Fumihito、Shohda, Miyuki、Taniguchi, Nobuaki、Fukumoto, Keiichiro

  DOI：——

  日期：——
• 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).