3-(9-methyl-9H-3-carbazolyl)-2-propenal | 460354-16-9

• 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: 3-(9-methyl-9H-3-carbazolyl)-2-propenal
• 英文别名: (2E)-3-(9-Methyl-9H-carbazol-3-yl)-2-propenal；(E)-3-(9-methylcarbazol-3-yl)prop-2-enal
• CAS: 460354-16-9
• 化学式: C₁₆H₁₃NO
• 分子量: 235.285
• InChiKey: HHRLNGAGSKGLIN-SNAWJCMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-(9-methyl-9H-3-carbazolyl)-2-propenal 在 Schwartz's reagent 、 sodium acetate 、 乙酸酐 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 4.25h， 生成 (4E)-4-[(2E,4E)-5-(9-methylcarbazol-3-yl)penta-2,4-dienylidene]-2-(4-nitrophenyl)-1,3-oxazol-5-one
  参考文献：
  名称：

  Synthesis of polyconjugated carbazolyl–oxazolones by a tandem hydrozirconation–Erlenmeyer reaction. Study of their hyperpolarizability values

  摘要：

  New push-pull systems with carbazole as donor moiety and oxazolone as electron withdrawing group have been synthesized by an AgClO4-catalyzed hydrozirconation and ulterior Erlenmeyer reaction. Studies carried out with the semiempirical quantum method PM3 (MOPAC93) pointed a low dependence of the hyperpolarizability value on the number of double bonds at the conjugated bridge by beta(0)proportional ton(0.8). Introduction of rigidity in the polyene chain or additional donor groups in the carbazole moiety pointed to exertion of a large effect on hyperpolarizability values that could avoid unnecessary efforts in costly path elongation synthesis. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00806-7
• 作为产物：
  描述：

  N-甲基咔唑 在 Schwartz's reagent 、 三氯氧磷 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 2.75h， 生成 3-(9-methyl-9H-3-carbazolyl)-2-propenal
  参考文献：
  名称：

  Synthesis of polyconjugated carbazolyl–oxazolones by a tandem hydrozirconation–Erlenmeyer reaction. Study of their hyperpolarizability values

  摘要：

  New push-pull systems with carbazole as donor moiety and oxazolone as electron withdrawing group have been synthesized by an AgClO4-catalyzed hydrozirconation and ulterior Erlenmeyer reaction. Studies carried out with the semiempirical quantum method PM3 (MOPAC93) pointed a low dependence of the hyperpolarizability value on the number of double bonds at the conjugated bridge by beta(0)proportional ton(0.8). Introduction of rigidity in the polyene chain or additional donor groups in the carbazole moiety pointed to exertion of a large effect on hyperpolarizability values that could avoid unnecessary efforts in costly path elongation synthesis. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00806-7