2-methoxy-5-methyl-5,6,7,8,9,10-hexahydrocycloheptindole | 51207-99-9

• 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: 2-methoxy-5-methyl-5,6,7,8,9,10-hexahydrocycloheptindole
• 英文别名: 5-methoxy-10-methyl-5,6,7,8,9,10-hexahydrocycloheptindole；2-methoxy-5-methyl-5,6,7,8,9,10-hexahydrocyclohepta[b]indole；5,6,7,8,9,10-Hexahydro-2-methoxy-5-methylcycloheptindol；5,6,7,8,9,10-Hexahydro-2-methoxy-5-methylcyclohept[b]indole；2-methoxy-5-methyl-7,8,9,10-tetrahydro-6H-cyclohepta[b]indole
• CAS: 51207-99-9
• 化学式: C₁₅H₁₉NO
• 分子量: 229.322
• InChiKey: QNYNIZXEJWNZNG-UHFFFAOYSA-N

物化性质

• 沸点：
  391.9±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)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 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：

  2-methoxy-5-methyl-5,6,7,8,9,10-hexahydrocycloheptindole 在 三氯化铝 、 乙硫醇 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以72%的产率得到1,2,3,4-tetrahydro-6-hydroxy-9-methylcarbazole
  参考文献：
  名称：

  5-甲氧基吲哚的选择性去甲基化和去甲氧基硫代烷基化

  摘要：

  摘要 在适当条件下，硬酸和软亲核试剂体系导致某些5-甲氧基吲哚选择性去甲基化和脱甲氧基硫代烷基化。

  DOI：

  10.1080/00397919408010187
• 作为产物：
  描述：

  3-氯-4-甲氧基苯胺 在 sodium amide 、 sodium t-butanolate 作用下， 以 四氢呋喃 、 叔丁醇 、 苯 为溶剂， 反应 64.0h， 生成 2-methoxy-5-methyl-5,6,7,8,9,10-hexahydrocycloheptindole
  参考文献：
  名称：

  Aggregative activation and heterocyclic chemistry I complex bases promoted arynic cyclisation of imines or enaminoketones; regiochemical synthesis of indoles

  摘要：

  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.

  DOI：

  10.1016/s0040-4020(01)89304-2

文献信息

• Formation of Enehydrazine Intermediates through Coupling of Phenylhydrazines with Vinyl Halides: Entry into the Fischer Indole Synthesis
  作者：Fuxu Zhan、Guangxin Liang

  DOI：10.1002/anie.201207173

  日期：2013.1.21

  Cut to the chase: Direct formation of an enehydrazine, an intermediate in the classic Fischer indole synthesis, solves the regioselectivity problem associated with indolization. This approach not only achieves selective synthesis of indoles through proper selection of the vinyl halide, but also leads to quick construction of desoxyeseroline and esermethole, as well as the key structural motif in the

  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。
• 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。
• Catalytic Cascade: Efficient Synthesis of Cyclohepta[b]indoles and Cyclohepta[b]indole‐Indoline Conjugates via RCM, Hydrogenation, and Acid‐Catalyzed Ring Expansion
  作者：Nabin Parui、Tirtha Mandal、Sandip Maiti、Jyotirmayee Dash

  DOI：10.1002/chem.202401059

  日期：——

  Efficient catalytic assembly for cyclohepta[b]indoles is achieved through sequential transformations: ring-closing metathesis, catalytic hydrogenation, and acid-catalyzed ring expansion. Ring closing metathesis (RCM) and hydrogenation of oxindoles yield spirocyclohexane-3-oxindoles. A subsequent spontaneous ring expansion-aromatization sequence, catalyzed by either Lewis or Brønsted acid, results in

  环庚[b]吲哚的有效催化组装是通过顺序转化实现的：闭环复分解、催化氢化和酸催化扩环。羟吲哚的闭环复分解（RCM）和氢化产生螺环己烷-3-羟吲哚。随后由路易斯或布朗斯台德酸催化的自发扩环芳构化序列产生环庚[ b ]吲哚或环庚[ b ]吲哚-二氢吲哚缀合物。
• Functionalisation of the alkoxy group of alkyl aryl ethers. Demethylation, alkylthiolation and reduction of 5-methoxyindoles
  作者：Catherine Caubère、Paul Caubère、Pierre Renard、Jean-Guy Bizot-Espiart、Sandra Ianelli、Mario Nardelli、Brigitte Jamart-Grégoiref

  DOI：10.1016/s0040-4020(01)89350-9

  日期：1994.1

  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.
• 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.