3-methoxy-11-methyl-5,6,7,8,9,10,11-heptahydrocyclooctindole | 153865-25-9

• 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-methoxy-11-methyl-5,6,7,8,9,10,11-heptahydrocyclooctindole
• 英文别名: 2-methoxy-5-methyl-6,7,8,9,10,11-hexahydro-5H-cycooctindole；2-Methoxy-5-methyl-6,7,8,9,10,11-hexahydrocycloocta[b]indole
• CAS: 153865-25-9
• 化学式: C₁₆H₂₁NO
• 分子量: 243.349
• InChiKey: SIKCGXUYQDQIFV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  14.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-methoxy-11-methyl-5,6,7,8,9,10,11-heptahydrocyclooctindole 在 三氯化铝 、 苄硫醇 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以96%的产率得到5,6,7,8,9,10,11-heptahydro-3-hydroxy-11-methylcyclooctindole
  参考文献：
  名称：

  Functionalisation of the alkoxy group of alkyl aryl ethers. Demethylation, alkylthiolation and reduction of 5-methoxyindoles

  摘要：

  In the presence of AlX(3)-RSH three kinds of reactions may take place with 5-methoxy indoles : demethylation, alkylthiolation and reduction. The two latter reactions have never been observed to the present, with such reagents. Considerable improvement in the selective demethylation was found when PhCH(2)SH replaced EtSH previously used in such transformations. Factors leading to selective alkylthiolations or reductions are shown and mechanisms are proposed to explain these new reactions.

  DOI：

  10.1016/s0040-4020(01)89350-9
• 作为产物：
  描述：

  环辛酮 在 亚磷酸三苯酯 、 copper(l) iodide 、 溴 、 potassium carbonate 、 N,N-二甲基乙二胺 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 45.0h， 生成 3-methoxy-11-methyl-5,6,7,8,9,10,11-heptahydrocyclooctindole
  参考文献：
  名称：

  通过苯肼与乙烯基卤化物的偶联形成中间体肼肼：进入费歇尔吲哚合成

  摘要：

  追逐目标：直接形成烯肼（Fischer吲哚经典合成中的中间体）可解决与吲哚化有关的区域选择性问题。这种方法不仅通过卤乙烯的适当选择实现吲哚的选择性合成，而且导致快速施工desoxyeseroline和esermethole的，以及在关键结构基序Akuammiline生物碱vincorine。

  DOI：

  10.1002/anie.201207173

文献信息

• Complex bases promoted arynic cyclisations of halogenated imines or enamines: A regiochemical synthesis of indole derivatives
  作者：Catherine Caubère、Paul Caubère、Pierre Renard、Jean-Guy Bizot-Espiart、Brigitte Jamart-Grégoire

  DOI：10.1016/s0040-4039(00)91822-7

  日期：1993.10

  The complex base NaNH2-tBuONa allows expeditious synthesis of indole derivatives by arynic cyclization of imines or enamines of chloroanilines. Unstable may be used without purification, complex bases being unsensitive to impurities.

  复杂的碱式NaNH 2 -tBuONa可以通过亚胺或氯苯胺的烯胺的芳基环化反应迅速合成吲哚衍生物。不稳定，无需纯化即可使用，复杂的碱对杂质不敏感。
• Aggregative activation and heterocyclic chemistry I complex bases promoted arynic cyclisation of imines or enaminoketones; regiochemical synthesis of indoles
  作者：Catherine Caubère、Paul Caubère、Sandra Ianelli、Mario Nardelli、Brigitte Jamart-Grégoire

  DOI：10.1016/s0040-4020(01)89304-2

  日期：1994.1

  The complex base NaNH2-t-BuONa allowed expeditious syntheses of indoles by arynic cyclisation of imines or enaminoketones prepared from halogeno anilines and carbonyl derivatives. Unstable imines may be used without purification, complex bases being unsensitive to impurities. It is showed that this kind of reaction may be applied to mixture of substrates suitably halogenated on the benzene ring. Formation of three components aggregates is proposed to explain a number of observations.
• Novel Indole-2-carboxamide and Cycloalkeno[1,2-<i>b</i>]indole Derivatives. Structure−Activity Relationships for High Inhibition of Human LDL Peroxidation
  作者：Catherine Kuehm-Caubere、Paul Caubere、Brigitte Jamart-Gregoire、Anne Negre-Salvayre、Dominique Bonnefont-Rousselot、Jean-Guy Bizot-Espiard、Bruno Pfeiffer、Daniel-Henri Caignard、Béatrice Guardiola-Lemaitre、Pierre Renard

  DOI：10.1021/jm960542k

  日期：1997.4.1

  Series of indole-2-carboxamide and cycloalkeno[1,2-b]indole derivatives were synthesized and evaluated in order to determine the necessary structural requirements for a high inhibition of human LDL copper-induced peroxidation. Various modulations were systematically performed on the indole and cycloalkeno[1,2-b]indole nuclei as well as on the carboxamide moiety. The best compounds (3c, 3e, 7c, 7f, 7h, 7g, and 7o) are between 5 and 30 times more active than probucol itself. Two of these compounds (3c and 70) were selected for complementary in vitro and in vivo investigations, which have shown additional properties of interest for the treatment and the prevention of atherosclerosis injuries. Compound 3e was found to have some antiinflammatory properties while compound 70 was proved to protect endothelial cells from the direct cytotoxicity of oxidized LDL with some additional calcium channel blocking properties.