N-(1-ethoxypropyl)carbazole | 68204-38-6

• 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: N-(1-ethoxypropyl)carbazole
• 英文别名: 9-(1-ethoxy-propyl)-carbazole；9-(1-Ethoxypropyl)-carbazol；9-(1-Ethoxypropyl)carbazole
• CAS: 68204-38-6
• 化学式: C₁₇H₁₉NO
• 分子量: 253.344
• InChiKey: CAZNEUXKDFXASB-UHFFFAOYSA-N

物化性质

• 熔点：
  87.5-88 °C(Solv: ethanol (64-17-5))
• 沸点：
  195-197 °C(Press: 3 Torr)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  14.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(1-ethoxypropyl)carbazole 在 吡啶 、 乙酰氯 作用下， 以 1,4-二氧六环 为溶剂， 反应 20.0h， 以62%的产率得到trans-9-propenylcarbazole
  参考文献：
  名称：

  The Cation Radical Chain Cycloaddition Polymerization of N,3-Bis(trans-1-propenyl)carbazole: The Critical Importance of Intramolecular Hole Transfer in Cation Radical Cycloaddition Polymerization

  摘要：

  The synthesis and polymerization of N,3-[bis (trans-1-propenyl)] carbazole (1) is reported. Using either the stable cation radical salt tris(4-bromophenyl)aminium hexachloroantimonate (2(+.)) or anodic oxidation to initiate the reaction, novel cycloaddition polymers are obtained in which the intermonomer linkages are of the cyclobutane, and to some extent of the Diels-Alder, type. A novel cation radical chain mechanism is proposed for the reaction, and extensive support for this mechanism is presented. The greatly enhanced reactivity of difunctional, as opposed to monofunctional, substrates in cation radical cycloadditions is dramatically highlighted by a comparison of the cycloaddition reactivity (rapid polymerization) of 1 versus N-propenylcarbazole (inefficient cyclodimerization) under electrochemical oxidation conditions. The sharply enhanced reactivity of 1 is attributed to the availability of intramolecular hole transfer in the bifunctional but not the monofunctional case.

  DOI：

  10.1002/1615-4169(200107)343:5<481::aid-adsc481>3.3.co;2-j
• 作为产物：
  描述：

  trans-9-propenylcarbazole 、 乙醇 以80%的产率得到
  参考文献：
  名称：

  FILIMONOV V. D.; ANFINOGENOV V. A.; SIROTKINA E. E., XIMIYA GETEROTSIKL. SOEDIN., 1979, HO 4, 497-502

  摘要：

  DOI：

文献信息

• FILIMONOV, V. D.;RODIONOV, V. A.;ANFINOGENOV, V. A.;SIROTKINA, E. E., ZH. ORGAN. XIMII, 1985, 21, N 6, 1256-1261
  作者：FILIMONOV, V. D.、RODIONOV, V. A.、ANFINOGENOV, V. A.、SIROTKINA, E. E.

  DOI：——

  日期：——
• ANFINOGENOV V. A.; FILIMONOV V. D.; SIROTKINA E. E., ZH. ORGAN. XIMII, 1978, 14, HO 8, 1723-1729
  作者：ANFINOGENOV V. A.、 FILIMONOV V. D.、 SIROTKINA E. E.

  DOI：——

  日期：——
• FILIMONOV V. D.; ANFINOGENOV V. A.; SIROTKINA E. E., ZH. ORGAN. XIMII, 1978, 14, HO 12, 2607-2611
  作者：FILIMONOV V. D.、 ANFINOGENOV V. A.、 SIROTKINA E. E.

  DOI：——

  日期：——
• The Cation Radical Chain Cycloaddition Polymerization of N,3-Bis(trans-1-propenyl)carbazole: The Critical Importance of Intramolecular Hole Transfer in Cation Radical Cycloaddition Polymerization
  作者：Yeonsuk Roh、Daxin Gao、Nathan L. Bauld

  DOI：10.1002/1615-4169(200107)343:5<481::aid-adsc481>3.3.co;2-j

  日期：2001.7

  The synthesis and polymerization of N,3-[bis (trans-1-propenyl)] carbazole (1) is reported. Using either the stable cation radical salt tris(4-bromophenyl)aminium hexachloroantimonate (2(+.)) or anodic oxidation to initiate the reaction, novel cycloaddition polymers are obtained in which the intermonomer linkages are of the cyclobutane, and to some extent of the Diels-Alder, type. A novel cation radical chain mechanism is proposed for the reaction, and extensive support for this mechanism is presented. The greatly enhanced reactivity of difunctional, as opposed to monofunctional, substrates in cation radical cycloadditions is dramatically highlighted by a comparison of the cycloaddition reactivity (rapid polymerization) of 1 versus N-propenylcarbazole (inefficient cyclodimerization) under electrochemical oxidation conditions. The sharply enhanced reactivity of 1 is attributed to the availability of intramolecular hole transfer in the bifunctional but not the monofunctional case.
• FILIMONOV V. D.; ANFINOGENOV V. A.; SIROTKINA E. E., XIMIYA GETEROTSIKL. SOEDIN., 1979, HO 4, 497-502
  作者：FILIMONOV V. D.、 ANFINOGENOV V. A.、 SIROTKINA E. E.

  DOI：——

  日期：——