1-(1-甲基吲哚-2-基)乙醇 | 29124-10-5

• 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
• 中文名称: 1-(1-甲基吲哚-2-基)乙醇
• 英文名称: 1-(1-methyl-1H-indol-2-yl)ethanol
• 英文别名: 1-Methyl-2-(α-hydroxyethyl)-indol；1-(1-methyl-indol-2-yl)-ethanol；2-(1-Methylindole)ethanol；1-(1-Methylindol-2-yl)ethanol
• CAS: 29124-10-5
• 化学式: C₁₁H₁₃NO
• 分子量: 175.23
• InChiKey: KKMMTRPLGRQILS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 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-(1-甲基吲哚-2-基)乙醇 在 2-碘酰基苯甲酸 作用下， 以 乙酸乙酯 为溶剂， 以1.1g的产率得到1-(1-甲基-1H-吲哚-2-基)乙酮
  参考文献：
  名称：

  通过不间断的炔丙基化/羟基苯甲酸酯化反应一锅法组装3-羟基咔唑。

  摘要：

  已经开发了一种新的合成3-羟基咔唑的策略，该策略涉及用炔丙醇进行吲哚-2-羰基的连续炔丙基化/钯催化的羟基化苯甲环化反应。这种一锅法可高产率地产生广泛范围的取代3-羟基咔唑，并具有广泛的底物范围。该方法进一步扩展为通过串联环环法从二烷基醇中获得呋喃并咔唑衍生物。

  DOI：

  10.1021/acs.orglett.9b04472
• 作为产物：
  描述：

  N-甲基-2-吡咯甲醛 在 methyl magnesium or lithium compound 作用下， 以 四氢呋喃 为溶剂， 生成 1-(1-甲基吲哚-2-基)乙醇
  参考文献：
  名称：

  二-和triheteroarylalkanes通过自缩合和分子内的杂芳基醇的弗里德尔-克拉夫茨型反应†

  摘要：

  通过Yb（III）催化2-糠基（或2-噻吩基或3-吲哚基）醇的顺序自缩合反应，然后进行分子内Friedel-Crafts型反应，开发了一种有效的合成方法，用于二杂芳基甲烷和1,3-二杂芳基丙烯。消除醛。该方法为传统的二杂芳基烷烃的合成提供了有力的途径和潜在的替代方法，后者是几种有趣的杂芳基化合物的合成的前体，更重要的是生物燃料的合成。

  DOI：

  10.1039/c3ob41945b

文献信息

• Pyranoindole derivatives as antiulcer agents
  申请人：Ayerst McKenna and Harrison Ltd.

  公开号：US04066780A1

  公开（公告）日：1978-01-03

  Pyranoindole and thiopyranoindole derivatives characterized by having an amino(lower)alkyl radical attached to either or both the 1 and 9 position of a pyrano[3,4-b]indole or thiopyrano[3,4-b]indole nucleus or having said radical attached to the 1 position of a pyrano[4,3-b]indole or thiopyrano[4,3-b]indole nucleus are disclosed. The amino portion of the amino(lower)alkyl radical may be further substituted with one or two lower alkyl groups or incorporated into a heterocyclic amine radical. The derivatives having the amino(lower)alkyl radical only at position 1 are further substituted at position 1 and may be optionally substituted at positions 3,4,5,6,7,8, and 9. The pyrano[3,4-b]indole or thiopyrano[3,4-b]indole derivatives having the amino(lower)alkyl radical only at position 9 possess two substitutents at position 1 and may be optionally substituted at position 3,4,5,6,7, and 8; the derivatives having an amino(lower)alkyl radical at both positions 1 and 9 are further substituted at position 1 and may be optionally substituted at positions 3,4,5,6,7 and 8. The pyrano-and thiopyranoindole derivatives of this invention are useful antidepressant and antiulcer agents. Methods for the preparation and use of these derivatives are also disclosed.

  Pyranoindole和thiopyranoindole衍生物的特征在于在pyrano[3,4-b]indole或thiopyrano[3,4-b]indole核的1和9位置之一或两者上附加有氨基(较低)烷基基团，或者在pyrano[4,3-b]indole或thiopyrano[4,3-b]indole核的1位置上附加有该基团。氨基(较低)烷基基团的氨基部分可能进一步被一个或两个较低烷基基团取代，或者被并入一个杂环胺基团。只在位置1具有氨基(较低)烷基基团的衍生物在位置1进一步被取代，并且可以选择在位置3,4,5,6,7,8和9处被取代。只在位置9具有氨基(较低)烷基基团的pyrano[3,4-b]indole或thiopyrano[3,4-b]indole衍生物在位置1处具有两个取代基，并且可以选择在位置3,4,5,6,7和8处被取代；在位置1和9处都具有氨基(较低)烷基基团的衍生物在位置1处进一步被取代，并且可以选择在位置3,4,5,6,7和8处被取代。本发明的pyrano和thiopyranoindole衍生物可用作抗抑郁和抗溃疡剂。还公开了这些衍生物的制备和使用方法。
• Synthesis of highly substituted indene derivatives by Brønsted acid catalyzed Friedel–Crafts reaction of homoallylic alcohols
  作者：Xiaoxiang Zhang、Wan Teng Teo、Weidong Rao、Dik-Lung Ma、Chung-Hang Leung、Philip Wai Hong Chan

  DOI：10.1016/j.tetlet.2014.05.027

  日期：2014.7

  An efficient synthetic method to prepare highly substituted indenes in moderate to excellent yields that relies on Brønsted acid catalyzed Friedel–Crafts reaction of homoallylic alcohols under mild conditions is described.

  描述了一种有效的合成方法，该方法以温和的条件下依赖于布朗斯台德酸催化的均丙醇的Friedel-Crafts反应来制备中等至优异收率的高度取代的茚满。
• Indolecarbonyl Coupling Reactions Promoted by Samarium Diiodide. Application to the Synthesis of Indole-Fused Compounds
  作者：Shu-Chen Lin、Fwu-Duo Yang、Jiann-Shyng Shiue、Shyh-Ming Yang、Jim-Min Fang

  DOI：10.1021/jo9720795

  日期：1998.5.1

  By the assistance of an N-sulfonyl group or a cyano group at the C-2 position, hydroxyalkylations of indole-3-carbonyls were achieved by the promotion of samarium diiodide. The indolecarbonyl coupling reactions proceeded in high stereoselectivity via chelate transition states. Intramolecular indolecarbonyl couplings of 1-(3-oxopropyl)indole-3-carboxaldehydes were realized as the indole-carbonyl group was more reactive toward SmI2 than the aliphatic carbonyl group. Elaboration of the coupling products with oxidizing agents, acid, phosphorus pentasulfide (or Lawesson's reagent), amines, and hydrazine led to a variety of indole derivatives and indole-fused polycyclic compounds of synthetic interest and pharmaceutical uses.
• Synthesis of β-heteroaryl propionates via trapping of carbocations with π-nucleophiles
  作者：Tsung-hao Fu、Amy Bonaparte、Stephen F. Martin

  DOI：10.1016/j.tetlet.2009.02.018

  日期：2009.7

  A variety of heterocyclic alcohols and acetates were Coupled with silyl ketene acetals and other pi-nucleophiles in the presence of trimethylsilyl trifluoromethanesulfonate to provide an array Of Substituted beta-heteroaryl propionates, including those with contiguous quaternary centers, as well as vinylogs thereof. This reaction also proceeds with high diastereoselectivity when the pi-nucleophile bears a chiral auxiliary. (C) 2009 Elsevier Ltd. All rights reserved.
• US4003913A
  申请人：——

  公开号：US4003913A

  公开（公告）日：1977-01-18