1-benzyl-5-chloro-1H-indole-3-carbaldehyde | 226883-77-8

• 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
• 英文名称: 1-benzyl-5-chloro-1H-indole-3-carbaldehyde
• 英文别名: 1-benzyl-5-chloroindole-3-carbaldehyde
• CAS: 226883-77-8
• 化学式: C₁₆H₁₂ClNO
• mdl: MFCD12027459
• 分子量: 269.73
• InChiKey: WREQGSQUZRGXDB-UHFFFAOYSA-N

物化性质

• 沸点：
  468.2±35.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  1-benzyl-5-chloro-1H-indole-3-carbaldehyde 在 potassium permanganate 、 N,N'-羰基二咪唑 作用下， 以 丙酮 为溶剂， 反应 16.0h， 生成 1-benzyl-5-chloro-N-(2-piperidin-1-ylethyl)indole-3-carboxamide
  参考文献：
  名称：

  Indole amide derivatives: synthesis, structure–activity relationships and molecular modelling studies of a new series of histamine H1-receptor antagonists

  摘要：

  A number of indole amide derivatives bearing a basic side chain, in which the indole ring replaces the isoster benzimidazole nucleus typical of some well-known antihistamines, were prepared and tested for their H-1-antihistaminic activity. The 1-benzyl-3-indolecarboxamides 32-42 showed antihistaminic (H-1) activity (pA(2) 6-8); the 3-indolylglyoxylylamides 7-16 and the 2-indolecarboxamides 48-56 showed little or no activity. Insertion of the basic side chain of the active 3-indolecarboxamide derivatives into a piperazine ring (compounds 57-59) led to a dramatic loss of activity. All the active compounds proved to be competitive antagonists, since the values of the regression slope were not statistically different from 1. The most active compounds, 32, 33, 38-41, were also tested both in vitro for their anticholinergic activity and in vivo for their ability to antagonize histamine-induced cutaneous vascular permeability in rats. The biological results and the structure-activity relationships of the novel compounds are discussed in the light of molecular modelling studies, taking the molecule of astemizole as a model, and referring to proposed H-1-receptor pharmacophore models. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(99)80044-0
• 作为产物：
  描述：

  5-氯吲哚 在 sodium hydride 、 三氯氧磷 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 2.58h， 生成 1-benzyl-5-chloro-1H-indole-3-carbaldehyde
  参考文献：
  名称：

  镍(II)催化吲哚与供体-受体环丙烷之间的形式[3+2]环加成反应

  摘要：

  本文描述了镍催化的区域和非对映选择性形式 [3+2] 环加成反应，N-取代吲哚和供体-受体环丙烷之间的加成反应，以合成环戊[b]吲哚。优化的反应条件提供了所需的含氮环加合物，产率高达 93%，dr 为 8.6:1，具有完全的区域选择性。该底物范围对各种取代的吲哚和环丙烷表现出高度耐受性，从而合成了六种新的环戊二烯[b]吲哚，并分离了文献中报道的五种衍生物。此外，通过 ESI-MS 在线反应监测研究了该反应的机理建议，从而可以识别 Ni(II) 催化过程中的反应中间体。 X射线晶体学证实了产物的结构和相关内切立体化学。该方法能够从容易获得的起始材料快速有效地构建稠合二氢吲哚。

  DOI：

  10.3390/molecules29071604

文献信息

• Domino Cyclodimerization of Indole-Derived Donor-Acceptor Cyclopropanes: One-Step Construction of the Pentaleno[1,6-a,b]indole Skeleton
  作者：Olga A. Ivanova、Ekaterina M. Budynina、Alexey O. Chagarovskiy、Eduard R. Rakhmankulov、Igor V. Trushkov、Alexander V. Semeykin、Nikolay L. Shimanovskii、Mikhail Ya. Melnikov

  DOI：10.1002/chem.201101687

  日期：2011.10.10

  The fellowship of the rings: The previously undiscovered ability of indole‐derived donor–acceptor cyclopropanes to involve four reaction centers simultaneously was revealed by their domino cyclodimerization (see scheme). This SnCl4‐induced reaction affords bisindole products with the pentaleno[1,6‐a,b]indole framework. In the course of this process, two new rings, three CC bonds, and four stereocenters

  环的团契：以前未被发现的吲哚衍生的供体-受体环丙烷同时参与四个反应中心的能力通过其多米诺环二聚反应得以揭示（参见方案）。SnCl 4诱导的反应提供了具有pentaleno [1,6- a，b ]吲哚骨架的双吲哚产物。在此过程中，形成了两个新的环，三个CC键和四个立体中心，它们具有出色的化学，区域和立体选择性。
• Catalytic Enantioselective Diels–Alder Reactions of Benzoquinones and Vinylindoles with Chiral Magnesium Phosphate Complexes
  作者：Yujia Bai、Jinping Yuan、Xiaoyue Hu、Jon C. Antilla

  DOI：10.1021/acs.orglett.9b01437

  日期：2019.6.21

  Tetrahydrocarbazole and its derivatives have received much attention due to the prevalence of this scaffold in natural products and their use in organic synthesis. We have developed a Diels–Alder reaction of benzoquinones and 3-vinylindoles catalyzed by chiral magnesium phosphate complexes to provide tetrahydrocarbazole derivatives in excellent yields and enantioselectivities (up to >99% yield, 99%

  由于该支架在天然产物中的普遍存在及其在有机合成中的用途，因此四氢咔唑及其衍生物受到了广泛的关注。我们已经开发了由手性磷酸镁络合物催化的苯醌和3-乙烯基吲哚的Diels-Alder反应，从而以优异的收率和对映选择性（高达> 99％，99％ee）提供四氢咔唑衍生物。这种转化具有广泛的底物范围，出色的对映选择性和温和的条件。
• HETEROCYCLIC COMPOUNDS AS ANTIBIOTIC POTENTIATORS
  申请人：THE UNIVERSITY OF NORTH CAROLINA AT CHAPEL HILL

  公开号：US20160168140A1

  公开（公告）日：2016-06-16

  The invention relates to heterocyclic compounds and their use as antibiotics and/or as antibiotic potentiators. The compounds may act as colistin potentiators and SOS inhibitors.

  这项发明涉及杂环化合物及其作为抗生素和/或抗生素增效剂的用途。这些化合物可能作为科利斯汀增效剂和SOS抑制剂起作用。
• Rhodium‐Catalyzed Vinyl Sulfonylation of 3‐Carbonyl‐Substituted Indoles with Ethenesulfonyl Fluoride by Cross‐Dehydrogenative Coupling: An Application in (3+2) Cycloaddition
  作者：K. Sandeep、A. Sanjeeva Kumar、K. C. Kumara Swamy

  DOI：10.1002/ejoc.202201037

  日期：2022.11.18

  An aldehyde-directed, Rh(III)-catalyzed site-selective C(4)−H vinyl sulfonylation of indoles with ESF (Ethene SulfonylFluoride) is reported. Potential synthetic utility of the products is demonstrated by using click chemistry to access indole C4-appended triazoles.

  报道了用 ESF（乙烯磺酰氟）对吲哚进行醛定向、Rh(III) 催化的位点选择性 C(4)-H 乙烯基磺酰化。通过使用点击化学来获得吲哚 C4 附加的三唑，证明了产品的潜在合成效用。
• Palladium‐Catalyzed C3‐Carbaldehyde Directed Regioselective C2‐Thioarylation of Indoles
  作者：Sandip Kumar Gupta、Niranjan Panda

  DOI：10.1002/asia.202400272

  日期：2024.6.3

  directing potential of weakly coordinating aldehyde group present at 3-position of indole was exploited for regioselective C2-H thioarylation over the possible C4-H functionalization. Mechanistic studies reveal that the process involves initial generation of thioaryl radical followed by sequential C−H activation, thiolate transfer, and reductive elimination.

  据报道，在苯基碘二乙酸酯存在下，二芳基二硫化物发生钯催化的吲哚硫代芳基化反应。利用吲哚 3 位弱配位醛基的定向潜力，对可能的 C4-H 官能化进行区域选择性 C2-H 硫代芳基化。机理研究表明，该过程涉及硫代芳基自由基的初始生成，随后依次进行 CH 激活、硫醇盐转移和还原消除。