1,2,3,4-tetrahydro-8-methoxy-9H-carbazole | 10257-96-2

• 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: 1,2,3,4-tetrahydro-8-methoxy-9H-carbazole
• 英文别名: 8-methoxy-2,3,4,9-tetrahydro-1H-carbazole；8-methoxy-1,2,3,4-tetrahydrocarbazole；8-methoxy-1,2,3,4-tetrahydro-carbazole；8-Methoxy-1,2,3,4-tetrahydro-carbazol；1-Methoxy-5,6,7,8-tetrahydro carbazol；8-Methoxy-1,2,3,4-tetrahydrocarbazol
• CAS: 10257-96-2
• 化学式: C₁₃H₁₅NO
• 分子量: 201.268
• InChiKey: QPJLVSWGLRAESM-UHFFFAOYSA-N

物化性质

• 沸点：
  205-210 °C(Press: 15 Torr)
• 密度：
  1.165±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  25
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,2,3,4-tetrahydro-8-methoxy-9H-carbazole 在 氢氧化钾 作用下， 以 二甲基亚砜 为溶剂， 反应 2.0h， 生成 1-(diethylamino)-3-(8-methoxy-1,2,3,4-tetrahydrocarbazol-9-yl)propan-2-ol
  参考文献：
  名称：

  Giancaspro; Pizzorno; Albonico, Il Farmaco, 1989, vol. 44, # 5, p. 483 - 493

  摘要：

  DOI：
• 作为产物：
  描述：

  (+/-)-cis-3a-[(trifluoroacetyl)amino]-1,2,3,3a,4,8b-hexahydro-5-methoxycyclopent[b]indole 以 xylene 为溶剂， 以100%的产率得到1,2,3,4-tetrahydro-8-methoxy-9H-carbazole
  参考文献：
  名称：

  Unambiguous characterisation of dienylimines as intermediates in Fischer indolisation of o-substituted N-trifluoroacetyl enehydrazines

  摘要：

  经系统研究，发现邻位取代的N-三氟乙酰烯酮肼通过二烯亚胺中间体进行热环化反应，并通过晶体衍射和光谱分析明确鉴定了这些中间体。

  DOI：

  10.1039/a907539i

文献信息

• Fischer Indole Synthesis with Organozinc Reagents
  作者：Benjamin A. Haag、Zhi-Guang Zhang、Jin-Shan Li、Paul Knochel

  DOI：10.1002/anie.201005319

  日期：2010.12.3

  Updated classic: Primary and secondary alkylzinc reagents add to various aryldiazonium salts leading regioselectively to polyfunctional indoles by means of a [3,3]‐sigmatropic shift and subsequent aromatization. This organometallic variation of the Fischer indole synthesis tolerates a wide range of functional groups and displays absolute regioselectivity.

  经典更新：烷基锌一级和二级试剂添加到各种芳基重氮盐中，通过[3,3]-σ移移和随后的芳构化作用，选择性地导致多官能吲哚。Fischer吲哚合成的这种有机金属变化可耐受各种官能团，并显示出绝对的区域选择性。
• Intramolecular cyclization of ortho-(cyclohex-2-enyl) anilines synthesis of ellipticine
  作者：A. G. Mustafin、I. N. Khalilov、E. V. Tal'vinskii、I. B. Abdrakhmanov、L. V. Spirikhin、G. A. Tolstikov

  DOI：10.1007/bf00630657

  日期：1992.9

  method is proposed for the synthesis of the alkaloid ellipticine, which possesses a pronounced antitumoral activity. The interaction of 3-bromocyclohexene (1 equiv.) and 2,5-xylylidine (4 equiv., 150°C, 5 h) gave a mixture of hexa- and tetrahydrocarbazoles which was dehydrogenated in the presence of Pd/C to the key synthon 1,4-dimethylcarbazole. The formylation of the carbazole by the Vilsmeier-Haack reaction

  提出了一种合成具有显着抗肿瘤活性的生物碱玫瑰树碱的简便方法。3-溴环己烯（1 当量）和 2,5-二甲苯胺（4 当量，150°C，5 小时）的相互作用产生六和四氢咔唑的混合物，在 Pd/C 存在下脱氢成为关键合成子 1,4-二甲基咔唑。通过 Vilsmeier-Haack 反应对咔唑进行甲酰化、与 2,2-二乙氧基乙胺的相互作用以及在雷尼镍上形成的亚胺的还原导致 3-(2,2-二乙氧基乙基氨基甲基)-1,4-二甲基咔唑，沸腾其 N-甲苯磺酸盐以高产率得到玫瑰树碱。
• Intramolecular cyclization ofortho-(cyclohex-2-enyl)anilines. Modified synthesis of ellipticine
  作者：A. G. Mustafin、I. N. Khalilov、R. R. Ismagilov、Z. M. Baimetov、L. V. Spirikhin、I. B. Abdrakhmanov、G. A. Tolstikov

  DOI：10.1007/bf02494860

  日期：1999.11

  It was found that the reactions of arylamines with 3-bromocyclohexene afforded hydrocarbazole compounds in 64-78% yields. A modified procedure for the synthesis of antitumor alkaloid ellipticine was proposed.
• Efficient synthesis of indoles using [3,3]-sigmatropic rearrangement of N-trifluoroacetyl enehydrazines
  作者：Okiko Miyata、Norihiko Takeda、Yasuo Kimura、Yoshiji Takemoto、Norimitsu Tohnai、Mikiji Miyata、Takeaki Naito

  DOI：10.1016/j.tet.2006.01.087

  日期：2006.4

  [3,3]-Sigmatropic rearrangement of N-triflluoroacetyl enehydrazines provides a novel method for the construction of indoles. N-Trifluoroacetyl enehydrazine having a cyclopentene ring smoothly underwent [3,3]-sign-tatropic rearrangement followed by cyclization to give indolines in excellent yield. On the other hand, both cyclohexenyl N-trifluoroacetyl enchydrazine and acyclic N-trifluoroacetyl enehydrazine gave indoles in good yield. Additionally, the substituent effect on the benzene ring was also studied. The rearrangement of N-trifluoroacetyl enchydrazines proceeded smoothly even Linder either aqueous or solvent-free conditions. (c) 2006 Elsevier Ltd. All rights reserved.
• McLean et al., Journal of the Chemical Society, 1955, p. 2519
  作者：McLean et al.

  DOI：——

  日期：——