ethyl 1-phenyl-9H-carbazole-2-carboxylate | 126979-11-1

• 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 1-phenyl-9H-carbazole-2-carboxylate
• CAS: 126979-11-1
• 化学式: C₂₁H₁₇NO₂
• 分子量: 315.371
• InChiKey: PPOHAFGLLPXJBY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  吲哚 、 ethyl 2-benzoyl-4-(tert-butylperoxy)-4-phenylbutanoate 在 三氟甲磺酸 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以65%的产率得到ethyl 1-phenyl-9H-carbazole-2-carboxylate
  参考文献：
  名称：

  Benzannulation of Indoles to Carbazoles and Its Applications for Syntheses of Carbazole Alkaloids

  摘要：

  A novel and efficient method for the benzannulation of indoles to carbzaoles is reported gamma-Carbonyl tert butylperoxide is applied as a new diene building block for the pi-extension of simple indoles. The synthetic utility of this method is demonstrated by concise and selective total syntheses of naturally occurring carbazole alkaloids, olivacine, and asteropusazole A.

  DOI：

  10.1021/ol5025053

文献信息

• Expedient Synthesis of Substituted Benzoheterocycles using 2-Butoxy-2,3-dihydrofurans as [4+2] Benzannulation Reagents
  作者：Changhui Liu、Wenbo Huang、Man Wang、Bin Pan、Yanlong Gu

  DOI：10.1002/adsc.201600185

  日期：2016.7.14

  2‐Alkoxy‐2,3‐dihydrofurans were found to be versatile benzannulation reagents. Indoles can be synthesized in good to excellent yields via the [4+2] annulation of 2‐butoxy‐2,3‐dihydrofuran with pyrroles catalyzed by copper bromide. With the same protocol, carbazoles can also be obtained when indoles are used as starting material with the aid of p‐toluenesulfonic acid. This type of benzannulation reagent

  发现2-烷氧基-2,3-二氢呋喃是通用的苯环化试剂。吲哚可以通过2-丁氧基-2,3-二氢呋喃与溴化铜催化的吡咯的[4 + 2]环合反应以良好的产率合成。按照相同的方案，当将吲哚用作对甲苯磺酸的起始原料时，也可以获得咔唑。在催化量的三氟甲磺酸存在下，这种类型的苯环化试剂也可用于合成苯并呋喃，苯并噻吩和萘衍生物。该苯环化方案具有广泛的底物范围和温和的反应条件。此外，大多数示例具有良好的区域反射性。
• Pindur, Ulf; Erfanian-Abdoust, Houshang, Liebigs Annalen der Chemie, 1990, # 8, p. 771 - 773
  作者：Pindur, Ulf、Erfanian-Abdoust, Houshang

  DOI：——

  日期：——
• PINDUR, ULF;ERFANIAN-ABDOUST, HOUSHANG, LIEBIGS ANN. CHEM.,(1990) N, C. 771-773
  作者：PINDUR, ULF、ERFANIAN-ABDOUST, HOUSHANG

  DOI：——

  日期：——
• Benzannulation of Indoles to Carbazoles and Its Applications for Syntheses of Carbazole Alkaloids
  作者：Xiaojian Zheng、Leiyang Lv、Shenglin Lu、Wenxiao Wang、Zhiping Li

  DOI：10.1021/ol5025053

  日期：2014.10.3

  A novel and efficient method for the benzannulation of indoles to carbzaoles is reported gamma-Carbonyl tert butylperoxide is applied as a new diene building block for the pi-extension of simple indoles. The synthetic utility of this method is demonstrated by concise and selective total syntheses of naturally occurring carbazole alkaloids, olivacine, and asteropusazole A.