ethyl 3-benzoyl-7-methylindolizine-1-carboxylate | 40624-45-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 3-benzoyl-7-methylindolizine-1-carboxylate
• 英文别名: 3-benzoyl-7-methyl-indolizine-1-carboxylic acid ethyl ester
• CAS: 40624-45-1
• 化学式: C₁₉H₁₇NO₃
• 分子量: 307.349
• InChiKey: GACJVTCYLJMTGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.66
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  47.78
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  ethyl 3-benzoyl-7-methylindolizine-1-carboxylate 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 24.0h， 生成 1H-benzo[d][1,2,3]triazol-1-yl 3-benzoyl-7-methylindolizine-1-carboxylate
  参考文献：
  名称：

  Novel indolizine derivatives with unprecedented inhibitory activity on human farnesyltransferase

  摘要：

  The rational structural modification of new substituted indolizin-3-yl(phenyl) methanones 1a-i, 2a-i and 3a-i has greatly improved human farnesyltransferase inhibition. The para-bromophenyl analog 2f bearing an ester unit on the indolizine ring demonstrates the highest inhibition potential, with IC50 value of 1.3 +/- 0.2 mu M. The amidic series 1a-i proves to be the most promising for future modulations, particularly at the triple bond level. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.10.044
• 作为产物：
  描述：

  4-甲基吡啶 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 ethyl 3-benzoyl-7-methylindolizine-1-carboxylate
  参考文献：
  名称：

  Novel indolizine derivatives with unprecedented inhibitory activity on human farnesyltransferase

  摘要：

  The rational structural modification of new substituted indolizin-3-yl(phenyl) methanones 1a-i, 2a-i and 3a-i has greatly improved human farnesyltransferase inhibition. The para-bromophenyl analog 2f bearing an ester unit on the indolizine ring demonstrates the highest inhibition potential, with IC50 value of 1.3 +/- 0.2 mu M. The amidic series 1a-i proves to be the most promising for future modulations, particularly at the triple bond level. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.10.044

文献信息

• Copper acetate monohydrate: a cheap but efficient oxidant for synthesizing multi-substituted indolizines from pyridinium ylides and electron deficient alkenes
  作者：Huayou Hu、Junjun Feng、Yulan Zhu、Ning Gu、Yuhe Kan

  DOI：10.1039/c2ra21213g

  日期：——

  We report a highly practical one-pot method for synthesizing multi-substituted indolizines from α-halide carbonyl compounds, pyridines and electron deficient alkenes in the presence of copper acetate monohydrate and sodium acetate in DMF. A variety of function groups are tolerable in standard reaction conditions, including aldehyde. 36 examples were presented. The yield of indolizine was from moderate to high. Furthermore, multi-substituted indolizines can be prepared at gram scale by this method.

  我们报道了一种高度实用的、一步合成多取代吲哚嗪的方法，该方法使用α-卤代羰基化合物、吡啶和缺电子烯烃，在醋酸铜一水合物和醋酸钠的DMF溶液中进行。在标准反应条件下，各种功能团（包括醛）都能耐受。我们提供了36个例子，吲哚嗪的产率从中等到高。此外，通过这种方法还能在克级规模上制备多取代吲哚嗪。
• One-pot synthesis of indolizine via 1,3-dipolar cycloaddition using a sub-equivalent amount of K₂Cr₂O₇ as an efficient oxidant under base free conditions
  作者：Chao Wang、Huayou Hu、Juanfang Xu、Weiqiu Kan

  DOI：10.1039/c5ra06019b

  日期：——

  X = Cl or Br; EWG₁, EWG₂ = electron withdrow group, one-pot reaction, 29 examples, yields from moderate to high, gram scale-up potential confirmed.

  X = 氯或溴；EWG1，EWG2 = 电子吸引基团，一锅法反应，29个例子，产率从中等到高，克级放大潜力得到确认。