4-氯-3-二甲氨基甲基吲哚 | 40247-57-2

• 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
• 中文名称: 4-氯-3-二甲氨基甲基吲哚
• 英文名称: 4-chloro-3-dimethylaminomethylindole
• 英文别名: 4-chlorogramine；(4-chloro-indol-3-ylmethyl)-dimethyl-amine；(4-Chlor-indol-3-ylmethyl)-dimethyl-amin；3-dimethyl-aminomethyl-4-chloroindole；1-(4-chloro-1H-indol-3-yl)-N,N-dimethylmethanamine
• CAS: 40247-57-2
• 化学式: C₁₁H₁₃ClN₂
• 分子量: 208.691
• InChiKey: QSRHZMVQLWOTMN-UHFFFAOYSA-N

物化性质

• 熔点：
  147.6-148.4 °C(Solv: acetone (67-64-1))
• 沸点：
  327.4±27.0 °C(Predicted)
• 密度：
  1.224±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  19
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  4-氯-3-二甲氨基甲基吲哚 在 4-二甲氨基吡啶 N-碘代丁二酰亚胺 、 TEA 作用下， 以 二氯甲烷 为溶剂， 反应 0.42h， 生成 4-氯-3-碘吲唑-1-羧酸叔一丁
  参考文献：
  名称：

  Rapid Route to 3,4-Substituted Indoles via a Directed Ortho Metalation−Retro-Mannich Sequence

  摘要：

  [GRAPHICS]In the presence of NXS (X = Br, I, Cl), gramine derivatives 1, derived by combined directed ortho metalation (DoM)-cross-coupling sequences, rapidly undergo retro-Mannich fragmentation (2) to afford 3-halo indoles 3 in 37-88% yields. A conceptually new methodology to diverse 3,4-substituted indoles (10, 11, 13) is thereby introduced.

  DOI：

  10.1021/ol017310m
• 作为产物：
  描述：

  methyl 4-chloro-indole-1-carboxylate 在 sodium hydroxide 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 18.25h， 生成 4-氯-3-二甲氨基甲基吲哚
  参考文献：
  名称：

  The chemistry of indoles. XVI. A convenient synthesis of substituted indoles carrying a hydroxy group, a halogeno group, or a carbon side chain at the 4-position via 4-indolediazonium salts and a total synthesis of (.+-.)-6,7-secoagroclavine.

  摘要：

  通过对 4-氨基吲哚衍生物进行重氮化，首次制备出了各种 4-吲哚重氮盐。它们经历了与一般炔重氮盐相似的各种反应，并被发现是制备在 4 位上带有羟基、卤代或氰基的取代吲哚的合适中间体。在 4-碘吲哚衍生物中引入各种碳侧链的尝试取得了令人满意的结果，而且还制备出了合成 (±)-6, 7-海泡石碱的关键中间体 4-（3-羟基）3-甲基-1-丁烯-1-基）吲哚。

  DOI：

  10.1248/cpb.29.3145

文献信息

• Tryptamine analogues, their synthesis and their use as 5-HT.sub.1 -like
  申请人：SmithKline Beecham plc

  公开号：US05571833A1

  公开（公告）日：1996-11-05

  The present invention relates to known and novel tryptamine analogues, processes and intermediates useful in their preparation, pharmaceutical compositions containing them and their use in therapy, in particular for the treatment and/or prophylaxis of disorders characterized by excessive vasodilatation, such as migraine and portal hypertension.

  本发明涉及已知和新颖的色胺类似物，用于制备它们的过程和中间体，含有它们的药物组合物以及它们在治疗中的使用，特别是用于治疗和/或预防由过度血管扩张所特征的疾病，如偏头痛和门静脉高压症。
• Hydrazone Compounds and Their Use
  申请人：STEIN Philip

  公开号：US20110033393A1

  公开（公告）日：2011-02-10

  The present invention relates to hydrazone compounds of Formula I: and pharmaceutically acceptable salts and stereoisomers thereof, wherein R 1 , R 2 , R 3 , R 4 , L 1 , and L 2 are defined as set forth in the specification. The invention is also directed to the use of compounds of Formula I as inhibitors of TRPM5 protein.

  本发明涉及式I的腙化合物及其药用可接受的盐和立体异构体，其中R1、R2、R3、R4、L1和L2的定义如规范中所述。本发明还涉及将式I的化合物用作TRPM5蛋白质的抑制剂。
• Transition-Metal-Free Base-Promoted Deaminative Coupling of Gramines with Aminomaleimides
  作者：Qiwen Gao、Liuting Luo、Chen Chen、Kangmei Wen、Zhibo Zhu、Xiaodong Tang

  DOI：10.1021/acs.joc.3c01610

  日期：2023.9.15

  The direct utilization of amines for C–C bond formation without prefunctionalization remains a significant challenge. Herein, we report the base-promoted deaminative coupling of gramines with aminomalaimides under redox-neutral conditions. In this operationally simple reaction, a series of indolmethyl-substituted aminomaleimides that emitted fluorescence were synthesized in good-to-excellent yields

  直接利用胺形成 C-C 键而不进行预官能化仍然是一个重大挑战。在此，我们报道了在氧化还原中性条件下碱促进的禾本科胺与氨基马来酰亚胺的脱氨基偶联。在这个操作简单的反应中，合成了一系列发出荧光的吲哚甲基取代的氨基马来酰亚胺，收率非常好。生物学评价显示，一些产品对人类癌细胞系表现出抗增殖活性。
• Cooperative Triple Catalysis Enables Deaminative α-Indolmethylation of Carbonyl Compounds with Gramines
  作者：Kangmei Wen、Chen Chen、Weiya Kong、Qiwen Gao、Jie Shi、Xiaodong Tang

  DOI：10.1021/acs.joc.3c02170

  日期：2024.1.19

  α-Functionalization of carbonyl compounds is an important reaction in synthetic chemistry. However, the development of novel synthetic strategies to realize this reaction is challenging. This study describes the α-indolmethylation of carbonyl compounds using cooperative copper, amine, and hydrogen-bond catalysis. This reaction provides a novel and efficient strategy for developing indolmethylated carbonyl compounds

  羰基化合物的α-官能化是合成化学中的重要反应。然而，开发新的合成策略来实现这种反应具有挑战性。本研究描述了使用铜、胺和氢键协同催化的羰基化合物的 α-吲哚甲基化。该反应为通过禾本科胺的脱氨偶联开发吲哚甲基化羰基化合物提供了一种新颖且有效的策略。
• Directed Lithiation of 1-Triisopropylsilylgramine. A Short Access to 3,4-Disubstituted Indoles
  作者：Masatomo Iwao

  DOI：10.3987/com-92-6185

  日期：——

  1-Triisopropylsilylgramine was lithiated regioselectively at C-4 by treatment with t-BuLi in ether at 0-degrees-C for 1 h. The lithiated species was trapped with a variety of electrophiles to furnish 4-functionalized gramine derivatives in good yields. Replacement of the triisopropylsilyl protecting group by a methyl group resulted in C-2 selective lithiation under the similar reaction conditions.