2,2-di(1H-indol-3-yl)ethan-1-ol | 95331-90-1

• 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: 2,2-di(1H-indol-3-yl)ethan-1-ol
• 英文别名: 2,2-bis(1H-indol-3-yl)ethanol
• CAS: 95331-90-1
• 化学式: C₁₈H₁₆N₂O
• 分子量: 276.338
• InChiKey: CEPLSEHCKRCRCO-UHFFFAOYSA-N

物化性质

• 熔点：
  47-49 °C(Solv: dichloromethane (75-09-2); ligroine (8032-32-4))
• 沸点：
  557.2±40.0 °C(Predicted)
• 密度：
  1.325±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  51.8
• 氢给体数：
  3
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,2-di(1H-indol-3-yl)ethan-1-ol 、 丁酸 在 4-二甲氨基吡啶 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以79%的产率得到arsindoline B
  参考文献：
  名称：

  One-Pot Construction of 3,3′-Bisindolylmethanes through Bartoli Indole Synthesis

  摘要：

  A one-pot approach to 3,3'-bisindolylmethane derivatives from nitrobenzene derivatives through the Bartoli indole synthesis was developed, in which the acid used to quench the reaction markedly affected its outcome. Quenching the reaction with concd HCl produced 3,3'-bisindolylmethane in contrast to the formation of 7-substituted indole by quenching with NH4Cl.

  DOI：

  10.1021/ol401486s
• 作为产物：
  描述：

  Di-indol-3-yl-essigsaeure 在 lithium aluminium tetrahydride 、 氯化亚砜 作用下， 以 乙醚 为溶剂， 反应 0.33h， 生成 2,2-di(1H-indol-3-yl)ethan-1-ol
  参考文献：
  名称：

  An Efficient Synthesis of Streptindole

  摘要：

  DOI：

  10.1055/s-1984-31004

文献信息

• Carbon transfer reactions with heterocycles-IV
  作者：Harjit Singh、Kamaljit Singh

  DOI：10.1016/s0040-4020(01)81447-2

  日期：1988.1

  Oxazolidines and tetrahydro-(2H)-1,3-oxazines transfer their C(2) units at the carbonyl group oxidation level to indoles and provide diindolylmethane derivatives. 2-Acetoxymethyl-4,4,6-trimethyltetrahydro-(2H)-1,3-oxazine and indole give streptindole.

  恶唑烷和四氢-（2H）-1,3-恶嗪将其C（2）单元在羰基氧化水平下转移至吲哚并提供二吲哚甲烷衍生物。2-乙酰氧基甲基-4,4,6-三甲基四氢-（2H）-1,3-恶嗪和吲哚生成链吲哚。
• Straight Access to Indoles from Anilines and Ethylene Glycol by Heterogeneous Acceptorless Dehydrogenative Condensation
  作者：Pedro Juan Llabres-Campaner、Rafael Ballesteros-Garrido、Rafael Ballesteros、Belén Abarca

  DOI：10.1021/acs.joc.7b02722

  日期：2018.1.5

  The development of original strategies for the preparation of indole derivatives is a major goal in drug design. Herein, we report the first straight access to indoles from anilines and ethylene glycol by heterogeneous catalysis, based on an acceptorless dehydrogenative condensation, under noninert conditions. In order to achieve high selectivity, a combination of Pt/Al2O3 and ZnO have been found to

  制备吲哚衍生物的原始策略的开发是药物设计的主要目标。本文中，我们报告了在非惰性条件下，基于无受体脱氢缩合反应，通过非均相催化从苯胺和乙二醇中首次直接获得吲哚。为了获得高选择性，已经发现Pt / Al 2 O 3和ZnO的组合物使乙二醇缓慢脱氢，在与胺缩合和互变异构平衡之后，生成相应的吡咯环未取代的吲哚。
• Solvent-Free Indoles Addition to Carbonyl Compounds Promoted by CeCl₃·7H₂O-NaI-SiO₂: An Efficient Method for the Synthesis of Streptindole
  作者：Enrico Marcantoni、Giuseppe Bartoli、Marcella Bosco、Gioia Foglia、Arianna Giuliani、Letizia Sambri

  DOI：10.1055/s-2004-815967

  日期：——

  Efficient electrophilic substitution reactions of indoles with various carbonyl compounds proceed easily in solvent-free conditions using CeCl3·7H2O-NaI-SiO2 system promoter, to afford the corresponding bis(1H-indol-3-yl)alkanes in high yields. The synthetic value of the present procedure is demonstrated by the synthesis of streptindole (9), human intestinal bacteria metabolite.

  在无溶剂条件下，使用CeCl3·7H2O-NaI-SiO2催化剂系统，吲哚与各种羰基化合物的高效亲电取代反应容易进行，生成相应的二(1H-吲哚-3-基)烷烃，产率高。通过合成抗生素streptindole（9），人类肠道细菌代谢物，证明了该方法的合成价值。
• 生物碱st reptindole及其衍生物在防治植物病毒病菌病中的应用
  申请人：天津师范大学

  公开号：CN113040151A

  公开（公告）日：2021-06-29

  本发明涉及一种生物碱streptindole及其衍生物在治疗植物病毒病菌病中的应用，本发明首次发现streptindole及其衍生物I‑1～I‑14表现出很好的抗植物病毒病菌活性，能很好地抑制烟草花叶病毒(TMV)和黄瓜枯萎，花生褐斑，苹果轮纹，小麦纹枯，玉米小斑，西瓜炭疽，水稻恶苗，番茄早疫，小麦赤霉，水稻稻瘟，辣椒疫霉，油菜菌核，黄瓜灰霉，水稻纹枯14种植物病菌。
• The Reactions of Nitrones with Indoles
  作者：Hélène Chalaye-Mauger、Jean-Noël Denis、Marie-Thérèse Averbuch-Pouchot、Yannick Vallée

  DOI：10.1016/s0040-4020(99)01051-0

  日期：2000.1

  The reaction of nitrones with various indole derivatives has been studied. When the reaction was promoted by ClSiMe3, the isolated products were 3,3'-diindolylalkanes. With HCl as the activating reagent, 3-indolylhydroxylamines were isolated. The diastereoselectivity of this condensation with a nitrone derived from cysteine was investigated. A method for the introduction of an alkylhydroxylamino group onto position 2 of indole, the synthesis of three natural 3,3'-diindolylalkanes and of non-symmetric diindolylalkanes are also reported. (C) 2000 Elsevier Science Ltd. All rights reserved.