4-(9H-carbazol-9-yl)butan-1-ol | 80772-72-1

• 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: 4-(9H-carbazol-9-yl)butan-1-ol
• 英文别名: 4-carbazol-9-ylbutan-1-ol
• CAS: 80772-72-1
• 化学式: C₁₆H₁₇NO
• mdl: MFCD12073850
• 分子量: 239.317
• InChiKey: AAYHPNFUILQYNU-UHFFFAOYSA-N

物化性质

• 沸点：
  435.4±37.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  25.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-(9H-carbazol-9-yl)butan-1-ol 在 N-溴代丁二酰亚胺(NBS) 、 三苯基膦 、 sodium t-butanolate 作用下， 以 N,N-二甲基乙酰胺 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.75h， 生成 9-(4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)butyl)-9H-carbazole
  参考文献：
  名称：

  碱介导的烷基砜自由基硼化反应

  摘要：

  据报道，在与 B 2 neop 2的碱介导的硼基化反应中，利用失活的烷基砜作为烷基自由基前体，从而无需进一步酯交换即可直接获得有价值的烷基硼酸酯。这种方法具有可扩展性，并且能够耐受各种官能团和底物，包括复杂分子。

  DOI：

  10.1002/chem.202103866
• 作为产物：
  描述：

  2-硝基联苯 在 盐酸 、 copper(l) iodide 、 copper diacetate 、 sodium carbonate 、 一水合肼 、 乙二醇 、 间氯过氧苯甲酸 、 sodium nitrite 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 异丙醇 为溶剂， 反应 19.33h， 生成 4-(9H-carbazol-9-yl)butan-1-ol
  参考文献：
  名称：

  通过将一锅铜催化的胺插入环状二苯并碘鎓中来合成咔唑，作为生成类似药物的化学文库的策略

  摘要：

  AbstractCarbazoles have attracted high interest among synthetic chemists due to their unique structural features and potential pharmacological activities. Compared to linear aryliodoniums, cyclic diphenyleneiodoniums are more inert and have not attracted much attention to their application as building blocks. Employing our synthetic strategy, diversified carbazoles can be efficiently obtained from a single cyclic diphenyleneiodonium under mild conditions. The reactions catalyzed by copper(II) acetate have provided a variety of carbazoles in modest to good yields with a broad range of amines including anilines, aliphatic amines and sulfonamides. Moreover, one of the obtained carbazoles has displayed an outstanding ability to protect HT‐22 neuronal cells from the damage induced by neurotoxins glutamate and homocysteic acid.magnified image

  DOI：

  10.1002/adsc.201300271
• 作为试剂：
  描述：

  4-(9H-carbazol-9-yl)butyl acetate 、 单水氢氧化锂 在 crude product 、 silica gel 、 乙酸乙酯 、 二氯甲烷 、 4-(9H-carbazol-9-yl)butan-1-ol 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以to yield 26 g (86%) of 4-(9H-carbazol-9-yl)butan-1-ol (Compound 10)的产率得到4-(9H-carbazol-9-yl)butan-1-ol
  参考文献：
  名称：

  IRIDIUM PHOSPHORESCENT DENDRIMER, METHOD OF PREPARING THE SAME AND ELECTROLUMINESCENT DEVICE INCLUDING THE IRIDIUM PHOSPHORESCENT DENDRIMER

  摘要：

  一种以公式1表示的铱磷光树状分子，其中A是基于咔唑的树状分支。还公开了一种制备铱磷光树状分子的方法以及包括铱磷光树状分子的电致发光装置。

  公开号：

  US20100084970A1

文献信息

• Design, synthesis and biological evaluation of <i>N</i>-arylsulfonyl carbazoles as novel anticancer agents
  作者：Xin You、Daqian Zhu、Wenhua Lu、Yichen Sun、Shuang Qiao、Bingling Luo、Yongliang Du、Rongbiao Pi、Yumin Hu、Peng Huang、Shijun Wen

  DOI：10.1039/c8ra02939c

  日期：——

  this work, a set of structurally diverse synthetic carbazoles was screened for their anticancer activities. According to structure–activity relationship studies, carbazoles with an N-substituted sulfonyl group exhibited better anticancer activity. Moreover, compound 8h was discovered to show the most potent anticancer effects on Capan-2 cells by inducing apoptosis and cell cycle arrest in G2/M phase

  在这项工作中，筛选了一组结构多样的合成咔唑的抗癌活性。根据构效关系研究，具有N-取代磺酰基的咔唑表现出更好的抗癌活性。此外，发现化合物8h通过诱导 G2/M 期细胞凋亡和细胞周期停滞对 Capan-2 细胞显示出最有效的抗癌作用。最后，体内研究表明，8h在 PANC-1 和 Capan-2 异种移植模型中阻止了肿瘤生长，没有明显的毒性。
• Synthesis of Heterocycle-linked Thioureas and Their Inhibitory Activities of NO Production in LPS Activated Macrophages
  作者：Ye-Jin Cheon、Hyo-Jin Gim、Hee-Ryun Jang、Jae-Ha Ryu、Raok Jeon

  DOI：10.5012/bkcs.2010.31.01.027

  日期：2010.1.20

  A series of thioureas were synthesized as inhibitors of NO production in lipopolysaccharide-activated macrophages. We investigated the effect of lipophilic moiety and N-substituents of the thioureas on the activity. Phenoxazine and carbazole-containing derivatives revealed higher activity than indole-containing thioureas. The appropriate spacer between lipophilic tail and thiourea head and methyl substituent at N3 position of thiourea brought beneficial effect on the inhibition of NO production. Among prepared compounds, phenoxazine-containing derivative 2a was the most potent with $2.32 \mu}M$ of $IC_50}$ value. RT-PCR analysis suggested that the prepared thioureas inhibited NO production through the suppression of iNOS mRNA expression.

  合成了一系列的硫脲作为脂多糖激活的巨噬细胞中NO产生的抑制剂。我们研究了硫脲的亲脂基团和N取代基对活性的影响。含有苯氧噻嗪和咔唑的衍生物表现出比含有吲哚的硫脲更高的活性。亲脂尾和硫脲头之间适当的间隔，以及在硫脲的N3位置上的甲基取代基对NO产生的抑制效果有利。 在所制备的化合物中，含有苯氧噻嗪的衍生物2a是最有效的，其< TEX>$IC_50}$值为< TEX>$2.32 \mu}M$。RT-PCR分析表明，所制备的硫脲通过抑制iNOS mRNA表达来抑制NO的产生。
• Hydroxyalkylation with Cyclic Sulfates: Synthesis of Carbazole Derived CB₂Ligands with Increased Polarity
  作者：Corinna Lueg、Fabian Galla、Bastian Frehland、Dirk Schepmann、Constantin G. Daniliuc、Winnie Deuther-Conrad、Peter Brust、Bernhard Wünsch

  DOI：10.1002/ardp.201300255

  日期：2014.1

  In order to increase the polarity of the potent CB2 ligand 1a, the homologous hydroxyalkyl carbazoles 2a–c were prepared and pharmacologically evaluated. An important step in the synthesis is the hydroxyalkylation of carbazole with cyclic sulfates providing the 2‐hydroxyethyl and 3‐hydroxypropyl derivatives 5a and 5b in a one‐step reaction. The final propionamides 2a–c were prepared using the recently

  为了增加有效的 CB2 配体 1a 的极性，制备了同源的羟烷基咔唑 2a-c 并对其进行了药理学评估。合成中的一个重要步骤是咔唑与环状硫酸盐的羟烷基化，在一步反应中提供 2-羟乙基和 3-羟丙基衍生物 5a 和 5b。最终的丙酰胺 2a-c 是使用最近报道的偶联试剂 COMU® 制备的。2c 的 X 射线晶体结构显示出 3-苯基-1,2,4-恶二唑联芳基系统的几乎共面排列。2a 极性增加与 CB2 亲和力降低近 100 倍有关。3-羟丙基衍生物 2b 代表了亲脂性和 CB2 亲和力之间的最佳折衷（Ki = 33 nM）。
• Iridium phosphorescent dendrimer, method of preparing the same and electroluminescent device including the iridium phosphorescent dendrimer
  申请人：Choi Dong-hoon

  公开号：US08420231B2

  公开（公告）日：2013-04-16

  An iridium phosphorescent dendrimer represented by Formula 1: wherein A is a carbazole-based dendron. Also disclosed is a method of preparing the iridium phosphorescent dendrimer and an electroluminescent device including the iridium phosphorescent dendrimer.

  一种以公式1所示的铱磷光树状分子为代表的铱磷光树状分子，其中A是基于咔唑的树状分子。还公开了制备铱磷光树状分子的方法以及包括铱磷光树状分子的电致发光装置。
• Manipulation of Förster Energy Transfer of Coupled Fluorophores Through Biotransformation by Pseudomonas resinovorans CA10
  作者：Michael A. Daniele、Yuriy P. Bandera、Stephen H. Foulger

  DOI：10.1111/j.1751-1097.2011.01023.x

  日期：2012.1

  AbstractAn alkyne‐terminated anthracene and azide‐terminated carbazole were joined through a copper‐catalyzed cycloaddition to form a joined donor/acceptor pair. The photonic pair exhibited energy transfer when excited at the peak absorbance of carbazole and fluoresced with an anthracene spectral response. The fluorescent behavior was confirmed as Förster energy transfer (FRET). The lysate of Pseudomonas resinovorans CA10, a member of a predominant group of soil microorganisms that can metabolize a host of substrates, was employed to degrade the pair and alter the luminance spectral characteristics. The FRET was diminished and the corresponding, individual fluorescence of carbazole and anthracene returned. This general approach may find applications in single‐cell metabolic studies and bioactivity assays.