ethyl 5-chloro-1-methyl-3-phenylindole-2-carboxylate | 21139-26-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: ethyl 5-chloro-1-methyl-3-phenylindole-2-carboxylate
• 英文别名: 5-chloro-1-methyl-3-phenyl-indole-2-carboxylic acid ethyl ester；5-Chlor-1-methyl-3-phenyl-indol-carbonsaeure-(2)-ethylester；5-Chloro-1-methyl-3-phenylindol-2-carbonsaeureethylester
• CAS: 21139-26-4
• 化学式: C₁₈H₁₆ClNO₂
• 分子量: 313.784
• InChiKey: OLNZCYBOYVBQDT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-甲氨基-5-氯二苯甲酮 在 dirhodium tetraacetate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲苯 为溶剂， 生成 ethyl 5-chloro-1-methyl-3-phenylindole-2-carboxylate
  参考文献：
  名称：

  Construction of Heterocyclic Compounds by Use of α-Diazophosphonates:  New One-Pot Syntheses of Indoles and Isocoumarins

  摘要：

  [GRAPHICS]alpha-Diazophosphonates, which have extremely useful properties from a synthetic point of view, are disclosed as 1,1-ambiphilic one-carbon building blocks for one-pot construction of various heterocyclic compounds. They are easily prepared and have higher stability by the effect of the phosphoryl group than corresponding alpha-diazocarbonyl compounds. Using this synthon, we have developed a novel, mild, and efficient synthetic method of 2,3-disubstituted indoles and 3,4-disubstituted isocoumarins.

  DOI：

  10.1021/ol025916k

文献信息

• The acid-promoted reactions of phenyliodonium ylides with substituted anilines and their applications to the synthesis of indoles
  作者：Xianpei Wang、Bing Han、Junyan Wang、Wei Yu

  DOI：10.1039/c0ob00201a

  日期：——

  N-substituted anilines 1 react readily with phenyliodonium ylides 2 derived from 1,3-dicarbonyl compounds in the presence of a catalytic amount of BF3·Et2O, forming the C–N coupling products 3, which are precursors for the synthesis of indoles. On the basis of this result, the direct synthesis of indoles from 1 and 2 under thermal conditions and photochemical conditions was explored. The transformations could

  这 ñ取代的苯胺1容易与苯碘鎓叶立德2衍生自1,3-二羰基在催化量的BF 3 ·Et 2 O存在下，这些化合物形成C–N偶联产物3，它们是吲哚合成的前体。基于该结果，探索了在热条件和光化学条件下从1和2直接合成吲哚的方法。转化可以在热条件下以单锅方式或在光化学条件下以串联方式实现。
• Reversed chemoselectivity in titanium-induced coupling reactions: syntheses of salvadoricine and diazepam
  作者：Alois Fürstner、Denis N. Jumbam

  DOI：10.1039/c39930000211

  日期：——

  Titanium/graphite-promoted indole formation is favoured over inter- as well as intra-molecular McMurry coupling as evidenced by chemoselective syntheses of compounds 2 and 5–7.

  钛/石墨促进的吲哚形成优于间以及分子内的McMurry偶合如由化合物的化学选择性合成2和5 - 7。