2-(3,4,7,9-tetrahydro-2H-pyrano[2,3-e]indol-8-one)-methanol | 190730-48-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 2-(3,4,7,9-tetrahydro-2H-pyrano[2,3-e]indol-8-one)-methanol
• 英文别名: 2-(hydroxymethyl)-3,4,7,9-tetrahydro-2H-pyrano[2,3-e]indol-8-one
• CAS: 190730-48-4
• 化学式: C₁₂H₁₃NO₃
• 分子量: 219.24
• InChiKey: YKSFVJWEGJSUEM-UHFFFAOYSA-N

物化性质

• 沸点：
  448.2±45.0 °C(Predicted)
• 密度：
  1.308±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(3,4,7,9-tetrahydro-2H-pyrano[2,3-e]indol-8-one)-methanol 在 三乙胺 作用下， 以 吡啶 、 乙醇 、 二甲基亚砜 为溶剂， 反应 2.0h， 生成 (S)-2-(Benzylamino-methyl)-3,4,7,9-tetrahydro-2H-pyrano[2,3-e]indol-8-one
  参考文献：
  名称：

  New generation dopaminergic agents 4. Exploiting the 2-methyl chroman scaffold. Synthesis and evaluation of two novel series of 2-(aminomethyl)-3,4,7,9-tetrahydro-2H-pyrano[2,3-e]indole and indol-8-one derivatives

  摘要：

  The rational design, synthesis, and evaluation of two novel series of 2-(aminomethyl)-3,4,7,9-tetrahydro-2H-pyrano[2,3-e]indole and indolone derivatives rue disclosed, based on the recently discovered D-2 agonist phenolic template prototype [i.e. the 7-OH-2-(aminomethyl)chroman nucleus]. The indolones were observed to have higher affinity and intrinsic activity than the corresponding indoles. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00349-4
• 作为产物：
  描述：

  (RS)-(7-tert-butoxycarbonylamino-8-methyl-chroman-2-yl)-methanol 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 2-(3,4,7,9-tetrahydro-2H-pyrano[2,3-e]indol-8-one)-methanol
  参考文献：
  名称：

  New generation dopaminergic agents 4. Exploiting the 2-methyl chroman scaffold. Synthesis and evaluation of two novel series of 2-(aminomethyl)-3,4,7,9-tetrahydro-2H-pyrano[2,3-e]indole and indol-8-one derivatives

  摘要：

  The rational design, synthesis, and evaluation of two novel series of 2-(aminomethyl)-3,4,7,9-tetrahydro-2H-pyrano[2,3-e]indole and indolone derivatives rue disclosed, based on the recently discovered D-2 agonist phenolic template prototype [i.e. the 7-OH-2-(aminomethyl)chroman nucleus]. The indolones were observed to have higher affinity and intrinsic activity than the corresponding indoles. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00349-4

文献信息

• 2-(aminomethyl)-3,4,7,9-tetrahydro-2H-pyrano-\x9b2,3-E!indol-8-ones and
  申请人：American Home Products Corporation

  公开号：US05750556A1

  公开（公告）日：1998-05-12

  Compounds of Formula I are selective autoreceptor agonists useful in treating disease states involving hyperactivity of dopamine systems: ##STR1## in which X is --(CH.sub.2).sub.n --; n is 1-3; R.sub.1 is hydrogen, alkyl, hydroxyalkyl, cycloalkyl-methyl, bicyclo-alkylmethyl or --(CH.sub.2).sub.m YAr; where m is 0-4, Y is --CH.sub.2 --, and Ar is phenyl, halophenyl, alkylphenyl, dialkylphenyl or alkoxyphenyl; R.sub.2 is hydrogen or alkyl; R.sub.3 is hydrogen, halogen, alkyl, alkoxy or hydroxy; or a pharmaceutically acceptable salt thereof.

  公式I的化合物是选择性自主受体激动剂，可用于治疗涉及多巴胺系统过度活跃的疾病状态：##STR1## 其中X为--(CH.sub.2).sub.n--; n为1-3; R.sub.1为氢、烷基、羟基烷基、环烷基甲基、双环烷基甲基或--(CH.sub.2).sub.m YAr; 其中m为0-4，Y为--CH.sub.2--，Ar为苯基、卤代苯基、烷基苯基、二烷基苯基或烷氧基苯基; R.sub.2为氢或烷基; R.sub.3为氢、卤素、烷基、烷氧基或羟基; 或其药学上可接受的盐。
• Chromane derivatives
  申请人：AMERICAN HOME PRODUCTS CORPORATION

  公开号：EP0771801B1

  公开（公告）日：1999-03-03
• JPH09169764A
  申请人：——

  公开号：JPH09169764A

  公开（公告）日：1997-06-30
• US5750556A
  申请人：——

  公开号：US5750556A

  公开（公告）日：1998-05-12
• New generation dopaminergic agents 4. Exploiting the 2-methyl chroman scaffold. Synthesis and evaluation of two novel series of 2-(aminomethyl)-3,4,7,9-tetrahydro-2H-pyrano[2,3-e]indole and indol-8-one derivatives
  作者：Richard E. Mewshaw、Karen L. Marquis、Xiaojie Shi、Georgia McGaughey、Gary Stack、Michael B. Webb、Magid Abou-Gharbia、Theodore Wasik、Rosemary Scerni、Taylor Spangler、Julie A. Brennan、Hossein Mazandarani、Joseph Coupet、Terrance H. Andree

  DOI：10.1016/s0040-4020(98)00349-4

  日期：1998.6

  The rational design, synthesis, and evaluation of two novel series of 2-(aminomethyl)-3,4,7,9-tetrahydro-2H-pyrano[2,3-e]indole and indolone derivatives rue disclosed, based on the recently discovered D-2 agonist phenolic template prototype [i.e. the 7-OH-2-(aminomethyl)chroman nucleus]. The indolones were observed to have higher affinity and intrinsic activity than the corresponding indoles. (C) 1998 Elsevier Science Ltd. All rights reserved.