1-methyl-2,3,4,9-tetrahydro-1H-carbazole | 17058-12-7

• 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: 1-methyl-2,3,4,9-tetrahydro-1H-carbazole
• 英文别名: 1-Methyl-1,2,3,4-tetrahydro-carbazol；1-methyl-1,2,3,4-tetrahydrocarbazole
• CAS: 17058-12-7
• 化学式: C₁₃H₁₅N
• 分子量: 185.269
• InChiKey: SARCNUIGPNZEDI-UHFFFAOYSA-N

物化性质

• 熔点：
  98 °C
• 沸点：
  185 °C
• 密度：
  1.098±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  15.8
• 氢给体数：
  1
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1-methyl-2,3,4,9-tetrahydro-1H-carbazole 在 platinum(IV) oxide 盐酸 、 氢气 作用下， 以 乙醇 为溶剂， 反应 8.0h， 以82%的产率得到4a-methyl-2,3,4,4a,9,9a-hexahydro-1H-carbazole
  参考文献：
  名称：

  酪氨酸羟化酶和多巴胺-β-羟化酶的潜在抑制剂

  摘要：

  合成了一系列甲基取代的1,2,3,4-四氢咔唑，并筛选了针对酪氨酸羟化酶和多巴胺-β-羟化酶的体外活性。评价了最有效的化合物对大鼠去甲肾上腺素生物合成的抑制作用。结果表明在三种剂量水平下去甲肾上腺素水平没有显着降低。

  DOI：

  10.1002/jps.2600731109
• 作为产物：
  描述：

  3-(pent-4-en-1-yl)-1H-indole 在 ruthenium trichloride silver trifluoromethanesulfonate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 38.0h， 以21%的产率得到1-methyl-2,3,4,9-tetrahydro-1H-carbazole
  参考文献：
  名称：

  Ru(III)-Catalyzed Cyclization of Arene-Alkene Substrates via Intramolecular Electrophilic Hydroarylation

  摘要：

  We herein report that RuCl3/AgOTf has proven to be a hydroarylation catalyst with an efficiency and scope superior to previously known methods. This catalyst demonstrated consistent performance with arene-ene substrates of diverse structural features, providing good to excellent yields of cyclization products (chromanes, tetralins, terpenoids, dihydrocoumarins).

  DOI：

  10.1021/ol036385i

文献信息

• Regiocontrolled Synthesis of Carbocycle-Fused Indoles via Arylation of Silyl Enol Ethers with <i>o</i>-Nitrophenylphenyliodonium Fluoride
  作者：Tetsuo Iwama、Vladimir B. Birman、Sergey A. Kozmin、Viresh H. Rawal

  DOI：10.1021/ol990759j

  日期：1999.8.1

  [formula: see text] A new, regiocontrolled synthesis of carbocycle-fused indoles has been developed. The two-step procedure involves first the regiospecific arylation of silyl enol ethers with o-nitrophenylphenyliodonium fluoride (1). Reduction of the nitro group on the aromatic ring with TiCl3 followed by spontaneous condensation of the aniline with the ketone then affords the indole products.

  [公式：见正文]已开发了一种新的，受区域控制的碳环稠合吲哚合成方法。分两步进行的程序涉及首先将甲硅烷基烯醇醚与邻硝基苯基苯基氟化碘鎓（1）进行区域特异性芳基化。用TiCl 3还原芳环上的硝基，然后苯胺与酮自发缩合，得到吲哚产物。
• Ene-hydrazide from Enol Triflate for the Regioselective Fischer Indole Synthesis
  作者：Byeong-Yun Lim、Bo-Eun Jung、Cheon-Gyu Cho

  DOI：10.1021/ol502031q

  日期：2014.9.5

  Ene-hydrazide prepared from enol triflate undergoes a Fischer indolization reaction to give the corresponding indole with complete regioselectivity. The starting enol triflate is readily accessed in regiochemically defined form from the ketone precursor via various well-established methods. This new protocol was successfully applied to the synthesis of desbromoarborescidine A, a natural β-carboline

  由三氟甲磺酸烯醇制备的乙酰肼经过费歇尔吲哚化反应，得到具有完全区域选择性的相应吲哚。起始烯醇三氟甲磺酸酯易于通过各种公认的方法从酮前体以区域化学定义的形式获得。该新方案已成功应用于合成天然Fischer吲哚难以制备的天然β-咔啉生物碱去溴阿糖胞苷A。
• Synthesis of 1,2,3,4-tetrahydrocarbazoles and related tricyclic indoles
  作者：Tricia L. Scott、Nicholas Burke、Grissell Carrero-Martínez、Björn C.G. Söderberg

  DOI：10.1016/j.tet.2006.11.052

  日期：2007.1

  Reduction of 2-(2-nitrophenyl)-2-cyclohexene-1-ones using palladium on carbon under 1 atm of hydrogen gas at ambient temperature affords 1,2,3,4-tetrahydrocarbazoles in excellent isolated yields. The starting materials were prepared by intermolecular Stille coupling of 2-iodo-2-cyclohexen-1-ones with 2-(tributylstannyl)-1-nitrobenzenes.

  在室温下在氢气中，在1个大气压下，使用钯碳还原2-（2-硝基苯基）-2-环己烯-1-酮，可得到1,2,3,4-四氢咔唑，分离产率极佳。通过2-碘-2-环己烯-1-酮与2-（三丁基锡烷基）-1-硝基苯的分子间Stille偶联制备起始原料。
• ß-CARBOLINE, DIHYDRO-ß-CARBOLINE AND TETRAHYDRO-ß-CARBOLINE ALKALOID DERIVATIVES AND PREPARATION METHODS SAME AND USE IN ASPECTS OF PREVENTING AND TREATING PLANT VIRUSES, FUNGICIDES AND INSECTICIDES
  申请人：NANKAI UNIVERSITY

  公开号：US20160326166A1

  公开（公告）日：2016-11-10

  The present invention relates to β-carboline, dihydro-β-carboline and tetrahydro-β-carboline alkaloid derivatives (I) and a method for preparing same and the use in the aspects of preventing and treating plant viruses, fungicides and insecticides. For the meaning of each group in formula (I) see the description. The β-carboline, dihydro-β-carboline and tetrahydro-β-carboline alkaloid derivatives of the present invention show a particularly ourstanding anti-plant virus activity, and also have fungicidal and insecticidal activities.

  本发明涉及β-咔啉、二氢β-咔啉和四氢β-咔啉生物碱衍生物(I)，以及其制备方法和在预防和治疗植物病毒、杀菌剂和杀虫剂方面的用途。本发明中的β-咔啉、二氢β-咔啉和四氢β-咔啉生物碱衍生物显示出特别出色的抗植物病毒活性，同时还具有杀菌和杀虫活性。
• Compositions and Methods for Viral Inhibition
  申请人：Ni Zhi-Jie

  公开号：US20070276009A1

  公开（公告）日：2007-11-29

  The present invention discloses methods and compositions for viral inhibition, particularly inhibition of HCV and SARS. The invention also provides compositions including carbazole derivatives useful for viral inhibition.

  本发明揭示了病毒抑制的方法和组合物，特别是对HCV和SARS的抑制。本发明还提供了包括咔唑衍生物的组合物，用于病毒抑制。