3-(2-hydroxyethyl)-5-methoxy-2-methylindole | 26766-01-8

• 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-(2-hydroxyethyl)-5-methoxy-2-methylindole
• 英文别名: 2-(5-methoxy-2-methyl-1H-indol-3-yl)-ethan-1-ol；2-(5-methoxy-2-methyl-1H-indol-3-yl)ethanol
• CAS: 26766-01-8
• 化学式: C₁₂H₁₅NO₂
• 分子量: 205.257
• InChiKey: VVIGWEDFRYYXJJ-UHFFFAOYSA-N

物化性质

• 熔点：
  102-103 °C(Solv: dichloromethane (75-09-2); hexane (110-54-3))
• 沸点：
  402.4±40.0 °C(Predicted)
• 密度：
  1.190±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：
  3
• 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-(2-hydroxyethyl)-5-methoxy-2-methylindole 在 4-二甲氨基吡啶 、 sodium hydride 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-[1-(4-Chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]ethyl 4-iodobenzoate
  参考文献：
  名称：

  Indolyl esters and amides related to indomethacin are selective COX-2 inhibitors

  摘要：

  Previous studies from our laboratory have revealed that esterification/amidation of the carboxylic acid moiety in the nonsteroidal anti-inflammatory drug, indomethacin, generates potent and selective COX-2 inhibitors. In the present study, a series of reverse ester/amide derivatives were synthesized and evaluated as selective COX-2 inhibitors. Most of the reverse esters/amides displayed time-dependent COX-2 inhibition with IC50 values in the low nanomolar range. Replacement of the 4-chlorobenzoyl group on the indole nitrogen with a 4-bromobenzyl moiety resulted in compounds that retained selective COX-2 inhibitory potency. In addition to inhibiting COX-2 activity in vitro, the reverse esters/amides also inhibited COX-2 activity in the mouse macrophage-like cell line, RAW264.7. Overall, this strategy broadens the scope of our previous methodology of neutralizing the carboxylic acid group in NSAIDs as a means of generating COX-2-selective inhibitors and is potentially applicable to other NSAIDs. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.07.073
• 作为产物：
  描述：

  methyl 2-(5-methoxy-2-methyl-1H-indol-3-yl)-2-oxoacetate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 3-(2-hydroxyethyl)-5-methoxy-2-methylindole
  参考文献：
  名称：

  铜（I）催化2-取代的三苯酚与芳基鎓盐的级联脱芳香化

  摘要：

  在随后的环化反应中，实现了铜（I）催化的2-取代的三苯酚的脱芳基芳基化和乙烯基化。级联脱芳香化序列提供了具有两个季碳中心的多用途呋喃二氢吲哚衍生物，收率好至极好。

  DOI：

  10.1021/ol301939w

文献信息

• 1H-Indole Derivatives as Calcium Antagonists
  作者：Laura Garuti、Giuseppe Giovanninetti、Sergio Bova、Alberto Chiarini

  DOI：10.1002/ardp.19883210702

  日期：——

  Two short series of compounds with 1H‐indole skeleton, bearing hydantoin and piperazine nuclei respectively, were synthesized. Some compounds of these two series were tested for their calcium‐antagonistic activity on K+‐depolarized smooth muscle (rabbit auricolar artery and guinea‐pig taenia caeci) and their negative inotropic action on atrial muscle from guinea‐pig hearts.

  合成了两个具有 1H-吲哚骨架的短系列化合物，分别带有乙内酰脲和哌嗪核。测试了这两个系列中的一些化合物对 K + 去极化平滑肌（兔耳廓动脉和豚鼠绦虫）的钙拮抗活性及其对豚鼠心脏心房肌的负性肌力作用。
• BF₃-Promoted Divergent Reactions between Tryptophols and Propargylic Alcohols
  作者：Kai Huang、Guorong Sheng、Ping Lu、Yanguang Wang

  DOI：10.1021/acs.orglett.7b01769

  日期：2017.8.4

  Trifluoroboron-promoted cascade reactions between tryptophols and propagylic alcohols furnished three types of skeletons, including carbazoles, cyclopenta[b]furo[2,3-b]indoles, and allenyl furo[2,3-b]indoles, with excellent selectivity based on the substrate structure. Tryptophols without a substituent on the 2-position of the indole ring reacted with 1,1,3-triphenylprop-2-yn-1-ol and 9-(phenyleth

  三氟化硼促进的tryptophols和propagylic醇之间的级联反应提供三种类型的骨架，包括咔唑，环戊二烯并[ b ]呋喃并[2,3- b ]吲哚，和丙二烯基呋喃并[2,3- b ]吲哚，具有优良的选择性基于基板结构。在吲哚环的2位上没有取代基的色酚与1,1,3-三苯基丙-2-yn-1-ol和9-（苯基乙炔基）-9 H-芴-9 -ol反应生成咔唑和环戊[b]呋喃并[2，3- b ]吲哚，而2-取代的三甲基酚反应生成了烯基呋喃并[2，3 - b ]吲哚。
• Asymmetric Fluorinative Dearomatization of Tryptophol Derivatives by Chiral Anion Phase-Transfer Catalysis
  作者：Xiao-Wei Liang、Yue Cai、Shu-Li You

  DOI：10.1002/cjoc.201800319

  日期：2018.10

  An asymmetric fluorinative dearomatization reaction of tryptophol derivatives was developed via chiral anion phase‐transfer catalysis. Various fluorinated furoindolines were obtained in moderate to excellent yields and enantioselectivity in the presence of Selectfluor. The preliminary mechanistic studies suggested the existence of an in situ formed tryptophol boronic ester plays a critical role in

  通过手性阴离子相转移催化开发了三氯酚衍生物的不对称氟化脱芳香化反应。在存在Selectfluor的情况下，以中等至极好的收率和对映选择性获得了各种氟化呋喃二氢。初步的力学研究表明，原位形成的胰多酚硼酸酯的存在在确定对映选择性方面起着至关重要的作用。该方法的特点是易于以高度对映选择性的方式引入氟原子，并构建了两个连续的四级立体异构中心。
• 1-Acyl-3-(amino-lower-alkyl)indoles
  申请人：Sterling Drug Inc.

  公开号：US04160862A1

  公开（公告）日：1979-07-10

  1-Acyl-3-(amino-lower-alkyl)indoles, useful as anti-inflammatory agents, are prepared either by acylation of a 3-(amino-lower-alkyl)indole; by Fisher indole synthesis from an N'-acylphenylhydrazine and an amino-lower-alkanone; by alkylation of an amine with a 1-acyl-3-(halo-lower-alkyl)indole; or by reductive alkylation of a 1-acyl-3-indole-lower-alkylcarboxaldehyde.

  1-酰基-3-(氨基低碳基)吲哚是一种有用的抗炎药物，可以通过以下方式制备：通过对3-(氨基低碳基)吲哚进行酰化反应；通过N'-酰基苯肼和氨基低碳酮的费舍尔吲哚合成反应；通过胺与1-酰基-3-(卤代低碳基)吲哚的烷基化反应；或通过1-酰基-3-吲哚-低碳基羧醛的还原烷基化反应制备。
• 3-(Piperidino-lower-alkyl)-indoles
  申请人：Sterling Drug Inc.

  公开号：US04021431A1

  公开（公告）日：1977-05-03

  1-Acyl-3-(amino-lower-alkyl)indoles, useful as anti-inflammatory agents, are prepared either by acylation of a 3-(amino-lower-alkyl)indole; by Fisher indole synthesis from an N'-acylphenylhydrazine and an amino-lower-alkanone; by alkylation of an amine with a 1-acyl-3-(halo-lower-alkyl)indole; or by reductive alkylation of a 1-acyl-3-indole-lower-alkylcarboxaldehyde.

  1-酰基-3-(氨基-较低烷基)吲哚是一种有用的抗炎剂，可以通过以下方法制备：通过对3-(氨基-较低烷基)吲哚进行酰化；通过使用N'-酰基苯肼和氨基-较低烷酮进行Fisher吲哚合成；通过使用1-酰基-3-(卤代-较低烷基)吲哚烷基化胺基；或通过还原烷基化1-酰基-3-吲哚-较低烷基羧醛制备。