5-甲氧基-A,A-二甲基-1H-吲哚-3-乙腈 | 896101-81-8

• 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
• 中文名称: 5-甲氧基-A,A-二甲基-1H-吲哚-3-乙腈
• 英文名称: 2-(5-methoxy-1H-indol-3-yl)-2-methylpropanenitrile
• 英文别名: 2-(5-methoxy-1H-indol-3-yl)-2-methylpropanonitrile；1H-Indole-3-acetonitrile, 5-methoxy-a,a-dimethyl-
• CAS: 896101-81-8
• 化学式: C₁₃H₁₄N₂O
• 分子量: 214.267
• InChiKey: ZHDVNWHEEPLIBL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  48.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-甲氧基-A,A-二甲基-1H-吲哚-3-乙腈 在 lithium aluminium tetrahydride 作用下， 以 乙醚 、 苯 为溶剂， 反应 0.75h， 生成 2-(5-methoxy-1H-indol-3-yl)-2-methylpropane-1-amine
  参考文献：
  名称：

  Mapping the Melatonin Receptor. 7. Subtype Selective Ligands Based on β-Substituted N-Acyl-5-methoxytryptamines and β-Substituted N-Acyl-5-methoxy-1-methyltryptamines

  摘要：

  A series of beta-substituted and beta,beta-disubstituted N-acyl 5-methoxy-1-methyltryptamines and 5-methoxy-tryptamines have been prepared as melatonin analogues to investigate the nature of the binding site of the melatonin receptor. The affinity of analogues was determined in a radioligand binding assay using cloned human MT(1) and MT(2) receptor subtypes expressed in NIH 3T3 cells. Agonist and antagonist potency of all analogues was measured using the pigment aggregation response of a clonal line of Xenopus laevis melanophores. beta-Methylmelatonin ( 17a) and beta,beta-dimethylmelatonin ( 17b), though showing a slight decrease in binding at human receptors, show an increase in potency on Xenopus. N-Butanoyl 5-methoxy-1-methyl-beta,beta-trimethylenetryptamine ( 12c) is an antagonist at human MT1 receptors but an agonist at MT2, while N-butanoyl 5-methoxy-1-methyl-beta,beta-tetramethylenetryptamine ( 13c) is an antagonist at MT1 but had no action at MT2 and is one of the first examples of an MT1 selective antagonist.

  DOI：

  10.1021/jm0512544
• 作为产物：
  描述：

  3- (1-氰基-1-甲基乙基)-5-甲氧基-1H-吲哚-1-羧酸--1,1-二甲基乙酯 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 以0.31 g的产率得到5-甲氧基-A,A-二甲基-1H-吲哚-3-乙腈
  参考文献：
  名称：

  Mapping the Melatonin Receptor. 7. Subtype Selective Ligands Based on β-Substituted N-Acyl-5-methoxytryptamines and β-Substituted N-Acyl-5-methoxy-1-methyltryptamines

  摘要：

  A series of beta-substituted and beta,beta-disubstituted N-acyl 5-methoxy-1-methyltryptamines and 5-methoxy-tryptamines have been prepared as melatonin analogues to investigate the nature of the binding site of the melatonin receptor. The affinity of analogues was determined in a radioligand binding assay using cloned human MT(1) and MT(2) receptor subtypes expressed in NIH 3T3 cells. Agonist and antagonist potency of all analogues was measured using the pigment aggregation response of a clonal line of Xenopus laevis melanophores. beta-Methylmelatonin ( 17a) and beta,beta-dimethylmelatonin ( 17b), though showing a slight decrease in binding at human receptors, show an increase in potency on Xenopus. N-Butanoyl 5-methoxy-1-methyl-beta,beta-trimethylenetryptamine ( 12c) is an antagonist at human MT1 receptors but an agonist at MT2, while N-butanoyl 5-methoxy-1-methyl-beta,beta-tetramethylenetryptamine ( 13c) is an antagonist at MT1 but had no action at MT2 and is one of the first examples of an MT1 selective antagonist.

  DOI：

  10.1021/jm0512544

文献信息

• Tris(pentafluorophenyl)borane-Catalyzed Formal Cyanoalkylation of Indoles with Cyanohydrins
  作者：Kensuke Kiyokawa、Naruyo Urashima、Satoshi Minakata

  DOI：10.1021/acs.joc.1c00808

  日期：2021.6.18

  cyanohydrins in the presence of a tris(pentafluorophenyl)borane (B(C6F5)3) catalyst. It is noteworthy that cyanohydrins are used as a cyanoalkylating reagent in the present reaction, even though they are usually used as only a HCN source. Mechanistic investigations revealed the unique reactivity of the B(C6F5)3 catalyst in promoting the decomposition of a cyanohydrin by a Lewis acidic activation through

  尽管在吲哚的 C3 官能化方面取得了重大成就，但氰基烷基化反应仍然相当有限。我们在此报告了在三（五氟苯基）硼烷（B（C 6 F 5）3）催化剂存在下，吲哚与氰醇的正式 C3 氰基烷基化反应。值得注意的是，氰醇在本反应中用作氰基烷基化试剂，尽管它们通常仅用作 HCN 源。机理研究揭示了 B(C 6 F 5 ) 3的独特反应性通过氰基与硼中心的配位，路易斯酸活化促进氰醇分解的催化剂。此外，还报道了使用吲哚、醛作为碳单元和丙酮氰醇的催化三组分反应，避免了每种醛衍生的氰醇的离散制备。所开发的方法为获得各种类型的合成有用的含有 α-叔或季碳中心的吲哚-3-乙腈衍生物提供了直接、高效和原子经济的途径。
• The discovery of carboline analogs as potent MAPKAP-K2 inhibitors
  作者：Jiang-Ping Wu、Ji Wang、Asitha Abeywardane、Denise Andersen、Michel Emmanuel、Elda Gautschi、Daniel R. Goldberg、Mohammed A. Kashem、Susan Lukas、Wang Mao、Leslie Martin、Tina Morwick、Neil Moss、Christopher Pargellis、Usha R. Patel、Lori Patnaude、Gregory W. Peet、Donna Skow、Roger J. Snow、Yancey Ward、Brian Werneburg、Andre White

  DOI：10.1016/j.bmcl.2007.05.101

  日期：2007.8

  The discovery of a series of potent, carboline-based MK2 inhibitors is described. These compounds inhibit MK2 with IC(50)s as low as 10 nM, as measured in a DELFIA assay. An X-ray crystal structure reveals that they bind in a region near the p-loop and the hinge region of MK2a. (c) 2007 Elsevier Ltd. All rights reserved.
• Mapping the Melatonin Receptor. 7. Subtype Selective Ligands Based on β-Substituted <i>N</i>-Acyl-5-methoxytryptamines and β-Substituted <i>N</i>-Acyl-5-methoxy-1-methyltryptamines
  作者：Andrew Tsotinis、Margarita Vlachou、Demetris P. Papahatjis、Theodora Calogeropoulou、Spyros P. Nikas、Peter J. Garratt、Vincent Piccio、Stefan Vonhoff、Kathryn Davidson、Muy-Teck Teh、David Sugden

  DOI：10.1021/jm0512544

  日期：2006.6.1

  A series of beta-substituted and beta,beta-disubstituted N-acyl 5-methoxy-1-methyltryptamines and 5-methoxy-tryptamines have been prepared as melatonin analogues to investigate the nature of the binding site of the melatonin receptor. The affinity of analogues was determined in a radioligand binding assay using cloned human MT(1) and MT(2) receptor subtypes expressed in NIH 3T3 cells. Agonist and antagonist potency of all analogues was measured using the pigment aggregation response of a clonal line of Xenopus laevis melanophores. beta-Methylmelatonin ( 17a) and beta,beta-dimethylmelatonin ( 17b), though showing a slight decrease in binding at human receptors, show an increase in potency on Xenopus. N-Butanoyl 5-methoxy-1-methyl-beta,beta-trimethylenetryptamine ( 12c) is an antagonist at human MT1 receptors but an agonist at MT2, while N-butanoyl 5-methoxy-1-methyl-beta,beta-tetramethylenetryptamine ( 13c) is an antagonist at MT1 but had no action at MT2 and is one of the first examples of an MT1 selective antagonist.