3,6-双(溴甲基)-9-乙基咔唑 | 174815-05-5

• 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
• 中文名称: 3,6-双(溴甲基)-9-乙基咔唑
• 英文名称: 3,6-bis(bromomethyl)-9-ethylcarbazole
• 英文别名: 3,6-bis(bromomethyl)-N-ethylcarbazole；3,6-Bis(bromomethyl)-9-ethyl-9H-carbazole
• CAS: 174815-05-5
• 化学式: C₁₆H₁₅Br₂N
• 分子量: 381.11
• InChiKey: XFSOZBXINMWQSD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  3,6-双(溴甲基)-9-乙基咔唑 在 sodium tetrahydroborate 作用下， 生成 24-Ethyl-3,16-diselena-24-azapentacyclo[16.2.2.15,9.18,11.110,14]pentacosa-1(21),5(25),6,8,10,12,14(23),18(22),19-nonaene
  参考文献：
  名称：

  Synthesis and Properties of [2.2]Paracyclo- and [2.2](1,4)Naphthaleno-(3,6)carbazolophanes

  摘要：

  [2.2]制备了(3,6)咔唑并(1a)和(1,4)萘并(3,6)咔唑并(1b)。1a和1b的结构通过1H NMR表征。1a的X射线分析表明，咔唑环与共轭平面偏离极大。1a和1b的电子光谱与参考光谱相比，出现了展宽和向红移。

  DOI：

  10.1246/cl.2002.934
• 作为产物：
  描述：

  9-乙基咔唑-3,6-二甲醛 在 sodium tetrahydroborate 、 氢溴酸 作用下， 以 乙醇 、 氯仿 为溶剂， 生成 3,6-双(溴甲基)-9-乙基咔唑
  参考文献：
  名称：

  Synthesis and Properties of Dioxa[3.3](3,6)carbazolophane

  摘要：

  通过3,6-双(羟甲基)咔唑与相应的二溴化物之间的环化反应合成了二氧杂[3.3](3,6)咔唑啉1。通过吸收和发射光谱检查了溶液中1的跨环π-π电子性质。通过X射线晶体分析证实了1的结构。

  DOI：

  10.1246/cl.1996.145

文献信息

• Exciplex Emission of Carbazole–Terephthalate Cyclophane and Its Application as a Fluorescent Probe for Local Polarity of Solvents
  作者：Hiroaki Benten、Hideo Ohkita、Shinzaburo Ito、Masahide Yamamoto、Yasuo Tohda、Keita Tani

  DOI：10.1246/bcsj.77.393

  日期：2004.2

  Photophysical properties of carbazole–terephthalate cyclophane (Cz–TP) were studied. The absorption spectra of Cz–TP in various solvents were slightly broadened due to the distortion of the carbazole (Cz) moiety and became similar to that of a reference compound of carbazole–benzene cyclophane (Cz–Bz). The absorption spectrum and the peak wavelengths of Cz–TP were insensitive to the solvent polarity. These findings show that there is transannular π–π electronic interaction between the Cz and TP moieties but that the charge transfer interaction from the Cz to TP moieties is small in the ground state. On the other hand, the emission spectrum was broad, structureless, and red-shifted compared with that of the reference compound. The peak wavelength of the emission was shifted to a longer wavelength with increases in the dielectric constant of solvents. The peak shift was quantitatively explained by the Lippert–Mataga formula. Therefore, we conclude that the broad emission is due to the intramolecular exciplex in Cz–TP. The dielectric constant of 2-methyl tetrahydrofuran was evaluated from the exciplex emission of Cz–TP ranging from 77 to 292 K, indicating that the Cz–TP molecule is an excellent polarity probe not only in a liquid phase but also in a solid phase over a wide temperature range.

  研究了咔唑-对苯二甲酸酯环芳烷（Cz-TP）的光物理性质。由于咔唑 (Cz) 部分的变形，Cz-TP 在各种溶剂中的吸收光谱略有展宽，并且与咔唑-苯环芳 (Cz-Bz) 参考化合物的吸收光谱相似。 Cz-TP 的吸收光谱和峰值波长对溶剂极性不敏感。这些发现表明，Cz 和 TP 部分之间存在跨环 π-π 电子相互作用，但基态下从 Cz 到 TP 部分的电荷转移相互作用很小。另一方面，与参考化合物相比，发射光谱较宽、无结构且红移。随着溶剂介电常数的增加，发射的峰值波长移动到更长的波长。峰移由 Lippert-Mataga 公式定量解释。因此，我们得出结论，宽发射是由于 Cz-TP 中的分子内激基复合物造成的。通过 Cz-TP 在 77 至 292 K 范围内的激基复合物发射评估了 2-甲基四氢呋喃的介电常数，表明 Cz-TP 分子不仅在液相中而且在固相中都是优异的极性探针。温度范围宽。
• Synthesis of novel carbazole based macrocyclic amides as potential antimicrobial agents
  作者：Perumal Rajakumar、Karuppannan Sekar、Vellasamy Shanmugaiah、Narayanasamy Mathivanan

  DOI：10.1016/j.ejmech.2008.07.031

  日期：2009.7

  A series of carbazole based macrocyclic diamides with thia and oxy linkages have been synthesized and the inhibitory activity of the cyclophane amides against human pathogenic bacteria and plant pathogenic fungi are documented. (S)-1,10-Bi-2-naphthol [(S)-BINOL] based chiral carbazolophane amide emerged as the most interesting compound in this series exhibiting excellent antibacterial and antifungal activities. (C) 2008 Elsevier Masson SAS. All rights reserved.
• Synthesis and properties of 4,4′-bipyridine based tetracationic carbazolophanes
  作者：Perumal Rajakumar、Karuppannan Sekar

  DOI：10.1016/j.tetlet.2006.04.012

  日期：2006.6

  The precyclophane derived from, 3,6-bis(bromomethyl) -9-ethylcarbazole and 5 equiv of 4,4'-bipyridine underwent macrocyclization on quaternization with various dibromides including 3,6-bis(bromomethyl)-9-ethylcarbazole to give carbazole-paraquat, self-complementary, cyclophanes revealing distinct charge-transfer and electrostatic interactions. The macrocyclic carbazolophane I was also obtained by a one-pot quaternization technique using equimolar amounts of 3,6-bis(bromomethyl)-9-ethylcarbazole and 4,4'-bipyridine. (c) 2006 Elsevier Ltd. All rights reserved.
• Synthesis and Properties of Dioxa[3.3](3,6)carbazolophane
  作者：Keita Tani、Yasuo Tohda、Kenji Hisada、Masahide Yamamoto

  DOI：10.1246/cl.1996.145

  日期：1996.2

  Dioxa[3.3](3,6)carbazolophane 1 has been synthesized by the cyclization reaction between 3,6-bis(hydroxymethyl)carbazole and corresponding dibromide. The transannular π-π electronic properties of 1 in solution were examined by absorption and emission spectra. The structure of 1 was confirmed by X-ray crystal analysis.

  通过3,6-双(羟甲基)咔唑与相应的二溴化物之间的环化反应合成了二氧杂[3.3](3,6)咔唑啉1。通过吸收和发射光谱检查了溶液中1的跨环π-π电子性质。通过X射线晶体分析证实了1的结构。
• Synthesis and Properties of [2.2]Paracyclo- and [2.2](1,4)Naphthaleno-(3,6)carbazolophanes
  作者：Keita Tani、Koh Matsumura、Kazushige Hori、Yasuo Tohda、Hiroyuki Takemura、Hideo Ohkita、Shinzaburo Ito、Masahide Yamamoto

  DOI：10.1246/cl.2002.934

  日期：2002.9

  [2.2]Paracyclo(3,6)carbazolophane (1a) and [2.2](1,4)naphthaleno(3,6)carbazolophane (1b) were prepared. The structures of 1a and 1b were characterized by 1H NMR. X-ray analysis of 1a revealed that the carbazole ring extremely deviates from the conjugated plane. Electronic spectra of 1a and 1b showed the broadening and bathochromic shift compared with the references.

  [2.2]制备了(3,6)咔唑并(1a)和(1,4)萘并(3,6)咔唑并(1b)。1a和1b的结构通过1H NMR表征。1a的X射线分析表明，咔唑环与共轭平面偏离极大。1a和1b的电子光谱与参考光谱相比，出现了展宽和向红移。