1-(4-chlorobenzyl)-1-phenylhydrazine | 100712-22-9

• 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-(4-chlorobenzyl)-1-phenylhydrazine
• 英文别名: 1-[(4-Chlorophenyl)methyl]-1-phenylhydrazine
• CAS: 100712-22-9
• 化学式: C₁₃H₁₃ClN₂
• 分子量: 232.713
• InChiKey: NQQHGPFWHYLFOZ-UHFFFAOYSA-N

物化性质

• 熔点：
  40-42 °C
• 沸点：
  180-185 °C(Press: 2-3 Torr)
• 密度：
  1.242±0.06 g/cm3(Predicted)

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：

  1-(4-chlorobenzyl)-1-phenylhydrazine 在 溶剂黄146 、 lithium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 0.5h， 生成 6'-chloro-1-(4-chlorobenzyl)-3-phenyl-1H,1'H-[2,3'-biindole]-2'-carboxylic acid
  参考文献：
  名称：

  2,3′-Bis(1′H-indole) heterocycles: New p53/MDM2/MDMX antagonists

  摘要：

  The protein-protein interaction of p53 and MDM2/X is a promising non genotoxic anticancer target. A rapid and efficient methodology was developed to synthesize the 2,3'-bis(1'H-indole) heterocyclic scaffold 2 as ester, acid and amide derivatives. Their binding affinity with MDM2 was evaluated using both fluorescence polarization (FP) assay and HSQC experiments, indicating good inhibition and a perfect starting point for further optimizations. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.11.019
• 作为产物：
  描述：

  2-[(4-Chlorophenyl)methylamino]isoindole-1,3-dione 在 copper diacetate 、 一水合肼 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 1-(4-chlorobenzyl)-1-phenylhydrazine
  参考文献：
  名称：

  A Convenient Synthesis of 1-Alkyl-1-phenylhydrazines fromN-Aminophthalimide

  摘要：

  N-Alkylaminophthalimides were synthesized by condensation of N-aminophthalimide with aldehydes, and subsequent reduction of the intermediate with pyridine-borane in acetic acid. N-Phenylation and removal of the phthalimide group gave 1-alkyl-1-phenylhydrazines in high yield.

  DOI：

  10.1081/scc-120015563

文献信息

• Reductive Hydrazination with Trichlorosilane: A Method for the Preparation of 1,1-Disubstituted Hydrazines
  作者：Tao Wang、Xiao Di、Chao Wang、Li Zhou、Jian Sun

  DOI：10.1021/acs.orglett.6b00675

  日期：2016.4.15

  and facile method has been developed to prepare 1,1-disubstituted hydrazines via Lewis base promoted direct reductive hydrazination. Under the catalysis of hexamethylphosphoramide (HMPA) and N,N-dimethylacetamide (DMAc), respectively, various ketones and aldehydes could react with phenylhdrazines to prepare 1,1-disubstituted hydrazines with good to high yields.

  已经开发了一种简单易行的方法，以通过路易斯碱促进的直接还原酰肼化来制备1,1-二取代的肼。分别在六甲基磷酰胺（HMPA）和N，N-二甲基乙酰胺（DMAc）的催化下，各种酮和醛可以与苯基乙嗪反应制备1,1-二取代肼，产率高至高。
• The Syntheses of Some Aminomethylindoles
  作者：Fumio Yoneda、Takayuki Miyamae、Yoshihiro Nitta

  DOI：10.1248/cpb.15.8

  日期：——

  By treating with secondary amines chloraceto-o-toluidide was converted to aminoaceto-o-toluidides, which were cyclized on heating with sodium amide to give 2-aminomethylindoles. N-Benzyl-N-(N, N-dimethylaminoaceto)-o-toluidide on treatment with sodium amide was converted to 1-benzyl-2-N, N-dimethylaminomethylindole. N-Benzyl-(or N-p-chlorobenzyl-) N-phenylhydrazine was treated with aminoacetones in the presence of a trace of acetic acid to convert the corresponding aminoacetone N-benzyl-(or N-p-chlorobenzyl-) N-phenylhydrazones. The indole cyclization of the latter gave 1-benzyl-2-methyl-3-aminoindoles. On treatment of aminoacetones with phenylhydrazine derivatives in ethyl alcohol, methylglyoxal diphenylhydrazone derivatives were obtained.

  用仲胺处理后，氯乙酰-邻甲基苯胺转化为氨基乙酰-邻甲基苯胺，用酰胺钠加热环化后得到 2-氨基甲基吲哚。N-苄基-N-（N，N-二甲氨基乙酰基）-邻甲基苯胺经酰胺钠处理后转化为 1-苄基-2-N，N-二甲氨基甲基吲哚。N-苄基-（或 N-对氯苄基-）N-苯肼与氨基丙酮在微量乙酸存在下进行处理，可转化为相应的氨基丙酮 N-苄基-（或 N-对氯苄基-）N-苯肼。后者的吲哚环化反应生成 1-苄基-2-甲基-3-氨基吲哚。在乙醇中用苯肼衍生物处理氨基丙酮，可得到甲基乙二醛二苯肼衍生物。
• 10.1021/acs.joc.4c00915
  作者：Shu, Shubing、Yu, Meng、Yu, Wenxin、Wang, Tao、Zhang, Zhenming

  DOI：10.1021/acs.joc.4c00915

  日期：——

  We present a PPh3/DDQ-mediated regiospecific selective N-functionalization of arylhydrazines with primary benzylic alcohols and aryl carboxylic acids for the synthesis of N1-benzyl arylhydrazines and N2-acyl arylhydrazines, respectively. This metal- and base-free approach features very short reaction times (about 10 min), broad substrate scope, good functional group tolerance, and mild reaction conditions

  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。
• DE930444
  申请人：——

  公开号：——

  公开（公告）日：——
• Derivatives of 2-nu-methyl-1, 2, 3, 4-tetrahydro-gamma-carbolines
  申请人：SCHENLEY IND INC

  公开号：US02786059A1

  公开（公告）日：1957-03-19