3-methyl-1,2,3,4-tetrahydrocyclopentindole | 1077-86-7

• 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: 3-methyl-1,2,3,4-tetrahydrocyclopentindole
• 英文别名: 1,2,3,4-tetrahydro-3-methylcyclopent[b]indole；3-methyl-1,2,3,4-tetrahydro-cyclopenta[b]indole；3-Methyl-1,2,3,4-tetrahydro-cyclopentaindol；3-Methyl-1,2,3,4-tetrahydrocyclopenta[b]indole
• CAS: 1077-86-7
• 化学式: C₁₂H₁₃N
• 分子量: 171.242
• InChiKey: SKTOZHWBDMGDDB-UHFFFAOYSA-N

物化性质

• 熔点：
  67-68 °C
• 沸点：
  314.8±11.0 °C(Predicted)
• 密度：
  1.134±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  3-methyl-1,2,3,4-tetrahydrocyclopentindole 、 碘甲烷 在 potassium tert-butylate 作用下， 以 乙醚 为溶剂， 反应 2.0h， 以94%的产率得到N,3-dimethyl-1,2,3,4-tetrahydrocyclopentindole
  参考文献：
  名称：

  Highly regioselective functionalization of 2,3-dialkyl substituents on indoles

  摘要：

  DOI：

  10.1021/jo00006a057
• 作为产物：
  描述：

  2-甲基环戊酮 在 2,4,6-三甲基吡啶 作用下， 以 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 生成 3-methyl-1,2,3,4-tetrahydrocyclopentindole
  参考文献：
  名称：

  Efficient synthesis of indoles using [3,3]-sigmatropic rearrangement of N-trifluoroacetyl enehydrazines

  摘要：

  [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.

  DOI：

  10.1016/j.tet.2006.01.087

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。
• Thermal cyclization of N-trifluoroacetyl enehydrazines under mild conditions: A novel entry into the fischer indole synthesis
  作者：Okiko Miyata、Yasuo Kimura、Kanami Muroya、Hajime Hiramatsu、Takeaki Naito

  DOI：10.1016/s0040-4039(99)00583-3

  日期：1999.4

  An efficient thermal cyclization of N-trifluoroacetyl enehydrazines for the synthesis of indoles is described.

  描述了用于合成吲哚的N-三氟乙酰基乙肼的有效热环化。
• Cycloalkanepyrrolopyridines as dp receptor antagonists
  申请人：Lachance Nicolas

  公开号：US20070027171A1

  公开（公告）日：2007-02-01

  Novel cycloalkanepyrrolopyridine derivatives are antagonists of prostaglandins, and as such are useful for the treatment of prostaglandin mediated diseases.

  新型环状烷基吡咯吡啶衍生物是前列腺素拮抗剂，因此可用于治疗前列腺素介导的疾病。
• Substituted indole derivatives
  申请人：GRÜNENTHAL GMBH

  公开号：US20130116283A1

  公开（公告）日：2013-05-09

  Substituted indole derivatives, processes for the preparation thereof, medicinal products and pharmaceutical compositions containing these compounds and the use of substituted indole derivatives to treat pain and other conditions and for other medical purposes.

  替代吲哚衍生物，其制备方法，含有这些化合物的药物产品和药物组合物，以及使用替代吲哚衍生物治疗疼痛和其他疾病以及其他医疗用途。
• Rodriguez, Jose-Gonzalo; Andres, Angel San, Journal of Heterocyclic Chemistry, 1991, vol. 28, # 5, p. 1293 - 1299
  作者：Rodriguez, Jose-Gonzalo、Andres, Angel San

  DOI：——

  日期：——