1-benzyl-1-(4-chlorophenyl)hydrazine | 35188-65-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-benzyl-1-(4-chlorophenyl)hydrazine
• CAS: 35188-65-9
• 化学式: C₁₃H₁₃ClN₂
• 分子量: 232.713
• InChiKey: YDLDGRGWTVZRNE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  29.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  叔丁基二甲基(2-丙炔氧基)硅烷 、 1-benzyl-1-(4-chlorophenyl)hydrazine 在 tetrakis(diethylamido)titanium(IV) 、 2,6-二叔丁基-4-甲基苯酚 、 zinc(II) chloride 作用下， 以 甲苯 为溶剂， 反应 48.0h， 生成 (1-Benzyl-5-chloro-2-methylindol-3-yl)oxy-tert-butyl-dimethylsilane
  参考文献：
  名称：

  合成3-（2-N，N-二乙基氨基乙氧基）吲哚作为潜在的5-HT6受体配体。

  摘要：

  描述了新的药物学上令人感兴趣的3-（2-N，N-二乙基氨基乙氧基）吲哚衍生物的合成。从3-甲硅烷氧基-2-甲基吲哚开始，脱保护和原位氨基烷基化以良好的产率提供了3-（2-N，N-二乙基氨基乙氧基）吲哚。这些新颖的吲哚的进一步磺酰化使访问潜在的5-HT（6）受体配体。

  DOI：

  10.1039/b802054j
• 作为产物：
  描述：

  苯甲醇 、 4-氯苯肼 在 三苯基膦 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 乙酸乙酯 为溶剂， 以64 %的产率得到1-benzyl-1-(4-chlorophenyl)hydrazine
  参考文献：
  名称：

  PPh3/DDQ 体系下芳基肼与伯醇和酸的选择性 N 官能化

  摘要：

  我们提出了PPh 3 /DDQ介导的芳基肼与伯苄醇和芳基羧酸的区域特异性选择性N-官能化，分别用于合成N 1 -苄基芳基肼和N 2 -酰基芳基肼。这种无金属、无碱的方法具有反应时间极短（约10分钟）、底物范围广、官能团耐受性好、反应条件温和等特点。此外， N 1 -苯甲基化产物还成功应用于N -取代吲哚和抗癌药物MDM2抑制剂的简洁合成。

  DOI：

  10.1021/acs.joc.4c00915

文献信息

• A Convenient and General Method for the Synthesis of Indole-2,3-dicarboxylates and 2-Arylindole-3-carboxylates
  作者：Iliyas Ali Sayyed、Karolin Alex、Annegret Tillack、Nicolle Schwarz、Dirk Michalik、Matthias Beller

  DOI：10.1002/ejoc.200700310

  日期：2007.9

  A transition-metal-free, simple and efficient one-pot method for the synthesis of indole-2,3-dicarboxylates and 2-arylindole-3-carboxylates is described. The corresponding products are obtained by a domino hydroamination/Fischerindole cyclization in good-to-excellent yields from easily available 1-alkyl-1-phenylhydrazines and acetylene carboxylates.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim

  描述了一种无过渡金属、简单有效的单锅法合成 indole-2,3-dicarboxylates 和 2-arylindole-3-carboxylates。相应的产物是通过多米诺加氢胺化/费歇吲哚环化以从容易获得的 1-烷基-1-苯肼和乙炔羧酸盐的良好收率获得的。 (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
• Titanium-Catalyzed Hydroamination of Propargyl Alcohol Derivatives: Synthesis of 3-Silyloxy-2-methylindoles via Hydrohydrazination
  作者：Matthias Beller、Nicolle Schwarz、Karolin Alex、Iliyas Sayyed、Vivek Khedkar、Annegret Tillack

  DOI：10.1055/s-2007-973892

  日期：2007.4

  A general method for the one-pot synthesis of substituted 3-(tert-butyldimethylsilyloxy)indoles via hydrohydrazination of alkynes and subsequent Fischer indole synthesis has been developed. For the first time titanium-catalyzed hydroaminations of ­propargyl alcohol derivatives are shown.

  通过炔烃的氢肼化和随后的费歇尔吲哚合成，开发出了一种单锅合成取代的 3-(叔丁基二甲基硅氧基)吲哚的通用方法。首次展示了钛催化的丙炔醇衍生物加氢氨化反应。
• Indole amide derivatives: synthesis, structure–activity relationships and molecular modelling studies of a new series of histamine H1-receptor antagonists
  作者：Sandra Battaglia、Enrico Boldrini、Federico Da Settimo、Giulio Dondio、Concettina La Motta、Anna Maria Marini、Giampaolo Primofiore

  DOI：10.1016/s0223-5234(99)80044-0

  日期：1999.2

  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.
• Hoerlein, Chemische Berichte, 1954, vol. 87, p. 463,467, 470
  作者：Hoerlein

  DOI：——

  日期：——
• Synthesis of 3-(2-N,N-diethylaminoethoxy)indoles as potential 5-HT6 receptor ligands
  作者：Karolin Alex、Nicolle Schwarz、Vivek Khedkar、Iliyas Ali Sayyed、Annegret Tillack、Dirk Michalik、Jörg Holenz、José Luis Díaz、Matthias Beller

  DOI：10.1039/b802054j

  日期：——

  The synthesis of new pharmaceutically interesting 3-(2-N,N-diethylaminoethoxy)indole derivatives is described. Starting from 3-silyloxy-2-methylindoles, deprotection and in situ aminoalkylation provided 3-(2-N,N-diethylaminoethoxy)indoles in good yield. Further sulfonylation of these novel indoles gave access to potential 5-HT(6) receptor ligands.

  描述了新的药物学上令人感兴趣的3-（2-N，N-二乙基氨基乙氧基）吲哚衍生物的合成。从3-甲硅烷氧基-2-甲基吲哚开始，脱保护和原位氨基烷基化以良好的产率提供了3-（2-N，N-二乙基氨基乙氧基）吲哚。这些新颖的吲哚的进一步磺酰化使访问潜在的5-HT（6）受体配体。