ethyl 2-(8-methoxy-3,4-dihydro-2H-thiopyrano[3,2-b]indol-5-yl)acetate | 162321-37-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl 2-(8-methoxy-3,4-dihydro-2H-thiopyrano[3,2-b]indol-5-yl)acetate
• CAS: 162321-37-1
• 化学式: C₁₆H₁₉NO₃S
• 分子量: 305.398
• InChiKey: OVYRCMCPTBVOCA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  65.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2-(8-methoxy-3,4-dihydro-2H-thiopyrano[3,2-b]indol-5-yl)acetate 在 三氯化铝 、 苄硫醇 作用下， 反应 2.5h， 以70%的产率得到ethyl 2-[5-hydroxy-2-(3-sulfanylpropyl)-1H-indol-1-yl]acetate
  参考文献：
  名称：

  Efficient selective synthesis of 2-substituted indoles from complex-base-promoted arynic cyclisations

  摘要：

  在络合碱 NaNH2-ButONa 的存在下，通过对甲基酮的卤代芳基亚胺进行选择性芳基环化，以及通过 PhCH2SH-AlCl3 开启四氢硫代吡喃吲哚（也是从亚胺的芳基环化中获得），可以有效地获得 2-取代的吲哚。

  DOI：

  10.1039/a702548c
• 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 、 N,N-二甲基甲酰胺 、 叔丁醇 、 苯 为溶剂， 反应 12.0h， 生成 ethyl 2-(8-methoxy-3,4-dihydro-2H-thiopyrano[3,2-b]indol-5-yl)acetate
  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

• 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.
• Efficient selective synthesis of 2-substituted indoles from complex-base-promoted arynic cyclisations
  作者：Catherine Kuehm-Caubère、Ivan Rodriguez、Bruno Pfeiffer、Pierre Renard、Paul Caubère

  DOI：10.1039/a702548c

  日期：——

  2-Substituted indoles have been efficiently obtained by selective arynic cyclisation of halogenated aryl imines of methyl ketones in the presence of the complex-base NaNH2–ButONa and by PhCH2SH–AlCl3 opening of tetrahydrothiopyranoindoles also obtained from arynic cyclisation of imines.

  在络合碱 NaNH2-ButONa 的存在下，通过对甲基酮的卤代芳基亚胺进行选择性芳基环化，以及通过 PhCH2SH-AlCl3 开启四氢硫代吡喃吲哚（也是从亚胺的芳基环化中获得），可以有效地获得 2-取代的吲哚。
• Novel thiopyrano[3,2-b] and cycloalkeno[1,2-b]indole derivatives with high inhibitory properties in LTB4 production
  作者：C KUEHMCAUBERE、P CAUBERE、B JAMARTGREGOIRE、B PFEIFFER、B GUARDIOLALEMAITRE、D MANECHEZ、P RENARD

  DOI：10.1016/s0223-5234(99)80040-3

  日期：1999.1