1-(1-Methyl-2-indolyl)-1-methylethanol | 29124-11-6

• 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: 1-(1-Methyl-2-indolyl)-1-methylethanol
• 英文别名: 2-(1-Methylindol-2-yl)propan-2-ol
• CAS: 29124-11-6
• 化学式: C₁₂H₁₅NO
• 分子量: 189.257
• InChiKey: BIDBPTAMBLIMKT-UHFFFAOYSA-N

物化性质

• 熔点：
  89-90 °C
• 沸点：
  342.7±17.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 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-Methyl-2-indolyl)-1-methylethanol 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 反应 15.0h， 以59%的产率得到2-异丙基-1-甲基-1H-吲哚
  参考文献：
  名称：

  Abbreviated Ibogaine Congeners. Synthesis and Reactions of Tropan-3-yl-2- and -3-indoles. Investigation of an Unusual Isomerization of 2-Substituted Indoles Using Computational and Spectroscopic Techniques

  摘要：

  The syntheses of several N-methyltropan-3-ylindoles, designed as congeners of ibogaine, are described. The synthetic approach to N-methyltropan-3-yl-2-indole revealed that the tropanyl 3'-center was quite sensitive to acid-catalyzed epimerization. The carbocyclic analog, N-methyl-2-[bicyclo[3.2.1]-oct-3-anyl] indole, also underwent this rearrangement. However, N-methyltropan-3-yl-3-indole was insensitive to acid or base, even under more vigorous conditions. This simple isomerization is quite rare for 2-substituted indoles, especially for cases where the center of reaction is not additionally activated, and normally only takes place under extreme reaction conditions. The mechanism of this reaction was investigated using ab initio molecular orbital calculations, NMR spectroscopy and deuterium labeling studies. These results indicate that, in contrast to those previously obtained for more reactive 2-substituted indoles, the reaction can best be explained using a simple exchange mechanism involving the exocyclic enamine tautomer of the indole ring as an intermediate. The difference in reactivity is suggested to arise from a decrease in the relative energy of the exocyclic enamine tautomer due to the presence of increased strain in the endo bicyclic 2-substituent. The title compounds displayed modest pharmacological activity in a variety of biological assays.

  DOI：

  10.1021/jo00087a037
• 作为产物：
  描述：

  1-甲基吲哚 、 丙酮 在 正丁基锂 作用下， 生成 1-(1-Methyl-2-indolyl)-1-methylethanol
  参考文献：
  名称：

  Akguen, Eyup; Tunali, Mustafa; Erdoenmez, Giray, Journal of Heterocyclic Chemistry, 1989, vol. 26, p. 1869 - 1873

  摘要：

  DOI：

文献信息

• Isoindole derivatives and salts thereof and antitumor agent comprising
  申请人：Toyama Chemical Co., Ltd.

  公开号：US05166204A1

  公开（公告）日：1992-11-24

  A novel isoindole derivative represented by general formula [1] or a salt thereof: ##STR1## which has an excellent antitumor activity and low toxicity.

  由一般式[1]表示的新型异吲哚衍生物或其盐：##STR1##具有优异的抗肿瘤活性和低毒性。
• Mild arylboronic acid catalyzed selective [4 + 3] cycloadditions: access to cyclohepta[b]benzofurans and cyclohepta[b]indoles
  作者：Kou-Sen Cao、Hong-Xu Bian、Wen-Hua Zheng

  DOI：10.1039/c5ob00653h

  日期：——

  The first example of arylboronic acid catalyzed [4 + 3] cycloaddition reaction is reported.

  第一个由芳基硼酸催化的[4 + 3]环加成反应的例子被报道。
• 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.
• AKGUN, EYUP;TUNALI, MUSTAFA;ERDONMEZ, GIRAY, J. HETEROCYCL. CHEM., 26,(1989) N, C. 1869-1873
  作者：AKGUN, EYUP、TUNALI, MUSTAFA、ERDONMEZ, GIRAY

  DOI：——

  日期：——
• US5166204A
  申请人：——

  公开号：US5166204A

  公开（公告）日：1992-11-24