5-cyclohexyl-1H-indole | 874948-87-5

• 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
• 英文名称: 5-cyclohexyl-1H-indole
• CAS: 874948-87-5
• 化学式: C₁₄H₁₇N
• 分子量: 199.296
• InChiKey: QLGVPOKOQQAAPZ-UHFFFAOYSA-N

物化性质

• 沸点：
  366.8±11.0 °C(Predicted)
• 密度：
  1.088±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  15.8
• 氢给体数：
  1
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  5-cyclohexyl-1H-indole 在 sodium methylate 、 sodium hydride 作用下， 以 甲醇 、 乙醚 、 乙腈 为溶剂， 反应 33.5h， 生成 1-(2-deoxy-β-D-erythropentafuranosyl)-5-cyclohexylindole
  参考文献：
  名称：

  Hydrophobicity, Shape, and π-Electron Contributions during Translesion DNA Synthesis

  摘要：

  Translesion DNA synthesis, the ability of a DNA polymerase to misinsert a nucleotide opposite a damaged DNA template, represents a common route toward mutagenesis and possibly disease development. To further define the mechanism of this promutagenic process, we synthesized and tested the enzymatic incorporation of two isosteric 5-substituted indolyl-2'deoxyriboside triphosphates opposite an abasic site. The catalytic efficiency for the incorporation of the 5-cyclohexene-indole derivative opposite an abasic site is 75-fold greater than that for the 5-cyclohexyl-indole derivative. The higher efficiency reflects a substantial increase in the k(pol) value (compare 25 versus 0.5 s(-1), respectively) as opposed to an influence on ground-state binding of either non-natural nucleotide. The faster k(pol) value for the 5-cyclohexene-indole derivative indicates that pi-electron density enhances the rate of the enzymatic conformational change step required for insertion opposite the abasic site. However, the kinetic dissociation constants for the non-natural nucleotides are identical and indicate that pi-electron density does not directly influence groundstate binding opposite the DNA lesion. Surprisingly, each non-natural nucleotide can be incorporated opposite natural templating bases, albeit with a greatly reduced catalytic efficiency. In this instance, the lower catalytic efficiency is caused by a substantial decrease in the k(pol) value rather than perturbations in ground-state binding. Collectively, these data indicate that the rate of the conformational change during translesion DNA synthesis depends on T-electron density, while the enhancement in ground-state binding appears related to the size and shape of the non-natural nucleotide.

  DOI：

  10.1021/ja0546830
• 作为产物：
  描述：

  4-环己苯胺 在 N-碘代丁二酰亚胺 、 copper(l) iodide 、 四(三苯基膦)钯 、 sodium ethanolate 、 palladium diacetate 、 碳酸氢钠 、 对甲苯磺酸 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 1,2-二氯乙烷 为溶剂， 反应 23.0h， 生成 5-cyclohexyl-1H-indole
  参考文献：
  名称：

  PLANT GROWTH REGULATOR

  摘要：

  提供一种能够更有效地发挥预期效果并减少任何意外效果的生长素衍生物。一种由通用式（1）表示的化合物，在生长素吲哚环的5-和/或6-位置具有特定取代基。

  公开号：

  US20210235697A1

文献信息

• Visible‐Light‐Promoted Iron‐Catalyzed C(sp ² )–C(sp ³ ) Kumada Cross‐Coupling in Flow
  作者：Xiao‐Jing Wei、Irini Abdiaj、Carlo Sambiagio、Chenfei Li、Eli Zysman‐Colman、Jesús Alcázar、Timothy Noël

  DOI：10.1002/anie.201906462

  日期：2019.9.9

  A continuous‐flow, visible‐light‐promoted method has been developed to overcome the limitations of iron‐catalyzed Kumada–Corriu cross‐coupling reactions. A variety of strongly electron rich aryl chlorides, previously hardly reactive, could be efficiently coupled with aliphatic Grignard reagents at room temperature in high yields and within a few minutes’ residence time, considerably enhancing the applicability

  为了克服铁催化的Kumada-Corriu交叉偶联反应的局限性，开发了一种连续流，可见光促进的方法。可以在室温下以高收率和数分钟的停留时间，在室温下与脂肪族格氏试剂有效地偶联各种以前几乎没有反应性的强电子富集的芳基氯化物，从而大大提高了这种铁催化反应的适用性。该协议的鲁棒性已在数克规模上得到了证明，从而为将来的药物应用提供了潜力。
• DNA-Accelerated Copper Catalysis of Friedel–Crafts Conjugate Addition/Enantioselective Protonation Reactions in Water
  作者：Almudena García-Fernández、Rik P. Megens、Lara Villarino、Gerard Roelfes

  DOI：10.1021/jacs.6b08295

  日期：2016.12.21

  the highest reported due to the environment presented by a biomolecular scaffold for any hybrid catalyst, to date. Based on a combination of kinetics and binding studies, it is proposed that the rate acceleration is in part due to the DNA acting as a pseudophase, analogous to micelles, in which all reaction components are concentrated, resulting in a high effective molarity. The involvement of additional

  DNA 诱导的速率加速已被确定为基于 DNA 的催化概念成功的关键因素之一。在这里，我们报告了一种新型的基于 DNA 的催化 Friedel-Crafts 共轭加成/对映选择性质子化反应在水中，它代表了一个反应的第一个例子，该反应严重依赖于 >700 到 990 倍的速率加速。 DNA 支架。迄今为止，由于任何混合催化剂的生物分子支架所呈现的环境，观察到的 DNA 诱导的速率加速是最高的。基于动力学和结合研究的结合，提出速率加速部分是由于 DNA 充当假相，类似于胶束，其中所有反应组分都被浓缩，从而产生高有效摩尔浓度。产品的对映选择性暗示了额外的第二配位球相互作用的参与。这里展示的结果令人信服地表明，由于 DNA 加速效应，基于 DNA 的催化概念可以成为在水中实现具有挑战性的化学反应的有效方法。
• 10.1021/acscatal.4c04002
  作者：Qiu, Canbin、Chen, Qifa、Gong, Hegui

  DOI：10.1021/acscatal.4c04002

  日期：——

  Barton-decarboxylative iodination to afford alkyl iodide as the actual coupling partners. The present method showcases a broad substrate scope for both alkyl acids and aryl/vinyl electrophiles. It offers the advantage of iodo-selectivity for the alkylation of aryl iodides, even those bearing highly competing bromine groups, including the challenging vicinal bromoiodobenzene. Consequently, it enables the development

  在这项工作中，我们利用烷基二酰基过氧化物作为脱羧底物，其衍生自易于获得的烷基酸与mCPBA的缩合，在镍催化的交叉亲电子偶联平台下与各种芳基和乙烯基卤化物偶联，有效地提供C(sp 3 )–C(sp 2 )键。该方法强调烷基二酰基过氧化物作为强氧化剂与 Ni/Zn 介导的还原条件的高度相容性。在 LiI 和催化 CuI 的帮助下，动力学不稳定的烷基二酰基过氧化物可以轻松地进行原位 Barton 脱羧碘化，得到烷基碘作为实际的偶联配偶体。本方法展示了烷基酸和芳基/乙烯基亲电子试剂的广泛底物范围。它为芳基碘化物的烷基化提供了碘选择性的优势，甚至是那些带有高度竞争性溴基团的芳基碘化物，包括具有挑战性的邻位溴碘苯。因此，它使得能够开发一锅选择性二烷基化工艺。
• A Modular, Air-Stable Nickel Precatalyst
  作者：Jason D. Shields、Erin E. Gray、Abigail G. Doyle

  DOI：10.1021/acs.orglett.5b00766

  日期：2015.5.1

  The synthesis and catalytic activity of [(TMEDA)Ni(o-tolyl)Cl], an air-stable, crystalline solid, is described. This complex is an effective precatalyst in a variety of nickel-catalyzed transformations. The lability of TMEDA allows a wide variety of ligands to be used, including mono- and bidentate phosphines, diimines, and N-heterocyclic carbenes. Preliminary mechanistic studies are also reported, which suggest that [(TMEDA)Ni(o-tolyl)Cl] can activate by either a Ni-B or Ni-Ni transmetalation event, depending on the reaction conditions.
• Ni/Photoredox-Catalyzed C(sp²)–C(sp³) Cross-Coupling of Alkyl Pinacolboronates and (Hetero)Aryl Bromides
  作者：Anthony N. Cauley、Antonio Ramirez、Chandan L. Barhate、Andrew F. Donnell、Purnima Khandelwal、Melda Sezen-Edmonds、Trevor C. Sherwood、Jack L. Sloane、Cullen L. Cavallaro、Eric M. Simmons

  DOI：10.1021/acs.orglett.2c01942

  日期：2022.8.12