3-(7-methoxy-1H-indol-3-yl)propan-1-ol | 29957-89-9

• 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-(7-methoxy-1H-indol-3-yl)propan-1-ol
• 英文别名: 3-(7-methoxy-indol-3-yl)-propan-1-ol；7-Methoxy-1H-indole-3-propanol
• CAS: 29957-89-9
• 化学式: C₁₂H₁₅NO₂
• 分子量: 205.257
• InChiKey: VYZAEDIFRGLVFI-UHFFFAOYSA-N

物化性质

• 沸点：
  413.0±30.0 °C(Predicted)
• 密度：
  1.188±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  45.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(7-methoxy-1H-indol-3-yl)propan-1-ol 在 吡啶 、 二甲基亚砜 、 N,N'-二环己基碳二亚胺 作用下， 以 氯苯 为溶剂， 反应 16.0h， 以38%的产率得到3-(7-methoxy-1H-indol-3-yl)propanal
  参考文献：
  名称：

  Advances toward New Antidepressants with Dual Serotonin Transporter and 5-HT_1A Receptor Affinity within a Class of 3-Aminochroman Derivatives. Part 2

  摘要：

  Novel compounds combining a 5-HT1A moiety (3-aminochroman scaffold) and a 5-HT transporter (indole analogues) linked through,a common basic nitrogen via an alkyl chain attached at the 1- or 3-position of the indole were evaluated for dual affinity at both the 5-HT reuptake site and the 5-HT1A receptor. Compounds of most interest were found to have a 5-carbamoyl-8-fluoro-3-amino-3,4-dihydro-2H-1-benzopyran linked to a 3-alkylindole (straight chain), more specifically substituted with a 5-fluoro ((R)-(-)-35c), 5-cyano ((-)-52a), or 5,7-difluoro ((-)-52g). Several factors contributed to 5-HT1A affinity, serotonin rat transporter affinity, and functional antagonism in vitro. Although most of our analogues showed good to excellent affinities at both targets, specific features such as cyclobutyl substitution on the basic nitrogen and stereochemistry at the 3-position of the chroman moiety seemed necessary for antagonism at the 5-HT1A receptor. Branched linkers seemed to impart antagonism even as racemates, however, potency of these analogues in the functional assay was not desirable enough to further pursue these compounds.

  DOI：

  10.1021/jm8007097
• 作为产物：
  描述：

  3,4-二氢-2H-吡喃 、 2-甲氧基苯肼盐酸盐 在 溶剂黄146 作用下， 以 水 为溶剂， 反应 3.0h， 以32%的产率得到3-(7-methoxy-1H-indol-3-yl)propan-1-ol
  参考文献：
  名称：

  对多环杂芳烃的无金属光氧好氧分子内脱氢环化反应

  摘要：

  我们通过吲哚与丙二酸的两个CH键实现了无金属的无氧好氧分子内脱氢偶联反应。该催化体系在室温下在可见光照射下以空气中的氧作为末端氧化剂进行，并以良好至极好的收率获得环化产物。

  DOI：

  10.1002/adsc.201600291

文献信息

• Rare Metal-Free Photo-Aerobic Intramolecular Dehydrogenative Cyclization Reaction towards Polycyclic Heteroarenes
  作者：Eiji Yamaguchi、Yusuke Sudo、Norihiro Tada、Akichika Itoh

  DOI：10.1002/adsc.201600291

  日期：2016.10.20

  We have achieved a rare‐metal‐free photo‐aerobic intramolecular dehydrogenative coupling reaction from two C—H bonds of indole with malonate. This catalytic system proceeded at room temperature under visible light irradiation with oxygen in the air as a terminal oxidant, and the cyclization products were obtained in good to excellent yields.

  我们通过吲哚与丙二酸的两个CH键实现了无金属的无氧好氧分子内脱氢偶联反应。该催化体系在室温下在可见光照射下以空气中的氧作为末端氧化剂进行，并以良好至极好的收率获得环化产物。
• Advances toward New Antidepressants with Dual Serotonin Transporter and 5-HT_1A Receptor Affinity within a Class of 3-Aminochroman Derivatives. Part 2
  作者：Nicole T. Hatzenbuhler、Reinhardt Baudy、Deborah A. Evrard、Amedeo Failli、Boyd L. Harrison、Steven Lenicek、Richard E. Mewshaw、Annmarie Saab、Uresh Shah、Jean Sze、Minsheng Zhang、Dahui Zhou、Michael Chlenov、Michael Kagan、Jeannette Golembieski、Geoffrey Hornby、Margaret Lai、Deborah L. Smith、Kelly M. Sullivan、Lee E. Schechter、Terrance H. Andree

  DOI：10.1021/jm8007097

  日期：2008.11.13

  Novel compounds combining a 5-HT1A moiety (3-aminochroman scaffold) and a 5-HT transporter (indole analogues) linked through,a common basic nitrogen via an alkyl chain attached at the 1- or 3-position of the indole were evaluated for dual affinity at both the 5-HT reuptake site and the 5-HT1A receptor. Compounds of most interest were found to have a 5-carbamoyl-8-fluoro-3-amino-3,4-dihydro-2H-1-benzopyran linked to a 3-alkylindole (straight chain), more specifically substituted with a 5-fluoro ((R)-(-)-35c), 5-cyano ((-)-52a), or 5,7-difluoro ((-)-52g). Several factors contributed to 5-HT1A affinity, serotonin rat transporter affinity, and functional antagonism in vitro. Although most of our analogues showed good to excellent affinities at both targets, specific features such as cyclobutyl substitution on the basic nitrogen and stereochemistry at the 3-position of the chroman moiety seemed necessary for antagonism at the 5-HT1A receptor. Branched linkers seemed to impart antagonism even as racemates, however, potency of these analogues in the functional assay was not desirable enough to further pursue these compounds.