1,2,3,4-tetrahydro-6-hydroxy-9-methylcarbazole | 156638-83-4

• 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-6-hydroxy-9-methylcarbazole
• 英文别名: 5-Methyl-5,6,7,8,9,10-hexahydrocyclohepta[b]indol-2-ol；5-methyl-7,8,9,10-tetrahydro-6H-cyclohepta[b]indol-2-ol
• CAS: 156638-83-4
• 化学式: C₁₄H₁₇NO
• 分子量: 215.295
• InChiKey: BAHOYABULMMMHV-UHFFFAOYSA-N

物化性质

• 沸点：
  414.8±40.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  25.2
• 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-6-hydroxy-9-methylcarbazole 、 乙硫醇 在 三氯化铝 作用下， 以 二氯甲烷 为溶剂， 以55%的产率得到3-ethylthio-10-methyl-5,6,7,8,9,10-hexahydrocycloheptindole
  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：

  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

文献信息

• 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.
• 7Caubere Catherine, Caubere Paul, Renard Pierre, Bizot-Espiart Jean-Guy, +, Synth. Commun, 24 (1994) N 13, S 1799-1808
  作者：7Caubere Catherine, Caubere Paul, Renard Pierre, Bizot-Espiart Jean-Guy, +

  DOI：——

  日期：——
• 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.
• Selective Demethylation and Demethoxy Thioalkylation of 5-Methoxyindoles
  作者：Catherine Caubère、Paul Caubère、Pierre Renard、Jean-Guy Bizot-Espiart、Brigitte Jamart-Grègoire

  DOI：10.1080/00397919408010187

  日期：1994.7

  Abstract Under appropriate conditions, hard acid and soft nucleophile system lead to selective demethylation and demethoxy- thioalkylation of certain 5-methoxyindoles.

  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。