5-chloro-1-ethylindole | 112194-57-7

• 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: 5-chloro-1-ethylindole
• 英文别名: 5-Chloro-1-ethyl-1H-indole
• CAS: 112194-57-7
• 化学式: C₁₀H₁₀ClN
• 分子量: 179.649
• InChiKey: RXECDNSWOFHZKW-UHFFFAOYSA-N

物化性质

• 沸点：
  290.7±13.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  5-chloro-1-ethylindole 在 叔丁基锂 、 二氧化硫 、 N-氯代丁二酰亚胺 作用下， 以 乙醚 、 正戊烷 、 二氯甲烷 为溶剂， 反应 8.0h， 以40%的产率得到(5-chloro-1-ethylindol-2-yl)sulfonyl chloride
  参考文献：
  名称：

  Design, synthesis, and biological activity of non-basic compounds as factor Xa inhibitors: SAR study of S1 and aryl binding sites

  摘要：

  Compound 7 was identified as the active metabolite of 6 by HPLC and mass spectral analysis. Modification of lead compound 7 by transformation of its N-oxide 6-6 biaryl ring system and fused aromatics produced a series of non-basic fxa inhibitors with excellent potency in anti-fXa and anticoagulant assays. The optimized compounds 73b and 75b showed sub to one digit micromolar anticoagulant activity (PTCT2). Particularly, anti-fXa activity was detected in plasma of rats orally administered with 1 mg/kg of compound 75b. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.04.006
• 作为产物：
  描述：

  溴乙烷 、 5-氯吲哚 在 potassium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 5-chloro-1-ethylindole
  参考文献：
  名称：

  Palladium catalyzed dual C–H functionalization of indoles with cyclic diaryliodoniums, an approach to ring fused carbazole derivatives

  摘要：

  正如标题反应所示，在单次操作中通过吲哚与环状二芳基碘鎓的双C-H官能化反应获得了一系列二苯并咔唑化合物。

  DOI：

  10.1039/c4ob02170c

文献信息

• NOVEL SULFONYL DERIVATIVES
  申请人：DAIICHI PHARMACEUTICAL CO., LTD.

  公开号：EP1104754A1

  公开（公告）日：2001-06-06

  Sulfonyl derivatives represented by the following general formula (I): Q1-Q2-T1-Q3-SO2-QA and drugs containing the same (wherein Q1 is an optionally substituted, saturated or unsaturated, five- or six-membered cyclic hydrocarbon group, a five- or six-membered heterocyclic group, or the like; Q2 is a single band, oxygen, sulfur, C1-C6 alkylene or the like; QA is optionally substituted arylalkenyl, heteroarylalkenyl or the like; and T1 is carbonyl or the like). These compounds have potent FXa-inhibitory effects and promptly exert satisfactory and persistent antithrombotic effects through oral administration, thus being useful as anticoagulant agents little accompanied with side effects.

  以下是通用公式（I）所代表的磺酰衍生物：Q1-Q2-T1-Q3-SO2-QA以及含有这些衍生物的药物（其中Q1是可选择地取代的饱和或不饱和的五元或六元环烃基团，五元或六元杂环基团等；Q2是单键，氧，硫，C1-C6烷基或类似物；QA是可选择地取代的芳基烯烃基团，杂环芳基烯烃基团或类似物；T1是羰基或类似物）。这些化合物具有强大的FXa抑制作用，并通过口服迅速产生令人满意且持久的抗血栓作用，因此可作为几乎不伴随副作用的抗凝血剂。
• Controllable synthesis of 3-chloro- and 3,3-dichloro-2-oxindoles <i>via</i> hypervalent iodine-mediated chlorooxidation
  作者：Xinpeng Jiang、Liechao Yang、Wenlong Yang、Yu Zhu、Liyun Fang、Chuanming Yu

  DOI：10.1039/c9ob01173k

  日期：——

  3-dichloro-2-oxindoles has been developed via hypervalent iodine-promoted chlorooxidation. By using two equivalents of 1-chloro-1,2-benziodoxol-3-(1H)-one, a wide range of indoles were transformed into 3-chloro-2-oxindoles in DMF/CF3CO2H/H2O at room temperature with good yields. As far as we know, this is the first report on the selective C-2 oxidation and C-3 monochlorination of simple indoles. In

  通过高价碘促进的氯氧化，已经开发出一种有效且可控制的合成3-氯-和3,3-二氯-2-氧吲哚的方案。通过在室温下使用两当量的1-氯-1,2-苯并恶唑-3-（1H）-一，将各种吲哚在DMF / CF3CO2H / H2O中转化为3-氯-2-氧吲哚。据我们所知，这是有关简单吲哚选择性C-2氧化和C-3单氯化的首次报道。此外，在优化的条件下（二恶烷/ H2O，80°C），三当量的相同高价碘以高达99％的产率提供3,3-二氯-2-氧吲哚。该方法具有温和的反应条件，广泛的底物可用性和良好的官能团耐受性。
• Mechanochemically Activated Oxidative Coupling of Indoles with Acrylates through C–H Activation: Synthesis of 3-Vinylindoles and β,β-Diindolyl Propionates and Study of the Mechanism
  作者：Kan-Yan Jia、Jing-Bo Yu、Zhi-Jiang Jiang、Wei-Ke Su

  DOI：10.1021/acs.joc.6b01138

  日期：2016.7.15

  Construction of 3-vinylindoles (3) and β,β-diindolyl propionates (4) through solvent-free C–H functionalization has been explored under high-speed ball-milling conditions. The reaction selectivity is influenced by the catalyst dramatically: Pd(OAc)2 provides 3 in moderate to good yields, whereas PdX2 (X = Cl, I) affords 4 as the major products. The reaction mechanism has been further studied by using

  在高速球磨条件下，已经探索了通过无溶剂的C–H功能化来构建3-乙烯基吲哚（3）和β，β-二吲哚基丙酸酯（4）。反应选择性受到催化剂的极大影响：Pd（OAc）2提供3到中等至良好的收率，而PdX 2（X = Cl，I）提供4作为主要产物。通过使用电喷雾电离质谱法进一步研究了反应机理，其中以二聚钯配合物A为关键中间体解释了选择性。
• Cu(ii)-catalyzed C–H (SP3) oxidation and C–N cleavage: base-switched methylenation and formylation using tetramethylethylenediamine as a carbon source
  作者：Lei Zhang、Chen Peng、Dan Zhao、Yue Wang、Hai-Jian Fu、Qi Shen、Jian-Xin Li

  DOI：10.1039/c2cc32009f

  日期：——

  Base-switched methylenation and formylation using tetramethylethylenediamine (TMEDA) as a carbon source have been achieved under mild conditions, catalyzed by CuCl(2), with atmospheric oxygen as oxidant. Bisindolylmethanes, diphenylmethanes and 3-formylindoles were synthesized with excellent regioselectivity and good yield.

  使用四甲基乙二胺（TMEDA）作为碳源的碱转换的甲基化和甲酰化反应已在温和的条件下实现，由CuCl（2）催化，大气中的氧气作为氧化剂。合成了双吲哚甲烷，二苯基甲烷和3-甲酰基吲哚，具有良好的区域选择性和良好的收率。
• Brønsted acidic ionic liquid–catalyzed tandem trimerization of indoles: An efficient approach towards the synthesis of indole 3,3′‐trimers under solvent‐free conditions
  作者：Rana Chatterjee、Sougata Santra、Grigory V. Zyryanov、Adinath Majee

  DOI：10.1002/jhet.3914

  日期：2020.4

  1‐butane sulfonic acid‐3‐methylimidazolium tosylate, [BSMIM]OTs, as an organocatalyst for the tandem type trimerization of indoles to synthesize indole 3,3′‐trimers under neat conditions. Using this developed protocol synthesis of indole trimers with various substituted indoles, which are biologically important, has been reported. From the control experiments and literature, a possible mechanism has

  我们已经观察到1-丁烷磺酸-3-甲基咪唑鎓甲苯磺酸盐[BSMIM] OTs在纯净条件下作为吲哚串联型三聚反应有机化合物合成吲哚3,3'-三聚体的作用。已经报道了使用这种开发的方案合成具有生物学重要性的各种取代的吲哚的吲哚三聚体。从对照实验和文献中，已经提出了通过在离子液体催化剂存在下生成吲哚阳离子的可能机理。催化剂已循环使用了几次。我们方法的显着优势是反应时间短，反应纯净，无需纯化即可进行色谱分离，可购得的底物，反应条件纯净且无金属。使用协议，