N-[1-(4-氯苯基)乙基氨基甲醛 | 188125-52-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-[1-(4-氯苯基)乙基氨基甲醛
• 英文名称: N-[1-(4-chloro-phenyl)-ethyl]-formamide
• 英文别名: N-[1-(4-chlorophenyl)ethyl]formamide；N-formyl-1-(4-chlorophenyl)ethylamine
• CAS: 188125-52-2
• 化学式: C₉H₁₀ClNO
• 分子量: 183.637
• InChiKey: CKHXBSSJPVBUNY-UHFFFAOYSA-N

物化性质

• 沸点：
  353.9±25.0 °C(Predicted)
• 密度：
  1.165±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-[1-(4-氯苯基)乙基氨基甲醛 在 盐酸 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 1.0h， 生成 1-(4-氯苯基)乙胺
  参考文献：
  名称：

  Bioinspired Organocatalytic Aerobic C–H Oxidation of Amines with an ortho-Quinone Catalyst

  摘要：

  A simple bioinspired ortho-quinone catalyst for the aerobic oxidative dehydrogenation of amines to imines is reported. Without any metal cocatalysts, the identified optimal ortho-quinone catalyst enables the oxidations of alpha-branched primary amines and cyclic secondary amines. Mechanistic studies have disclosed the origins of different performances of ortho-quinone vs para-quinone in biomimetic amine oxidations.

  DOI：

  10.1021/acs.orglett.5b00351
• 作为产物：
  描述：

  对氯苯乙酮 在 甲酸 、 formamide 作用下， 生成 N-[1-(4-氯苯基)乙基氨基甲醛
  参考文献：
  名称：

  N-(.alpha.-alkylbenzylidene)-.alpha.-phenylalkylamine, its use and

  摘要：

  公开了一种由通式（1）表示的N-（α-烷基苯基亚甲基）-α-苯基烷胺：其中R.sup.1代表较低的烷基基团，R.sup.2代表氢原子、卤原子、较低的烷基基团或较低的烷氧基团，X代表卤原子或较低的烷氧基团，其用途及其生产方法，以及用于生产其中间体的方法。

  公开号：

  US05739401A1

文献信息

• N-(alpha-alkylbenzylidene)-alpha-phenylalkylamine, its use and process for producing the same and process for producing intermediate therefor
  申请人：SUMITOMO CHEMICAL COMPANY LIMITED

  公开号：EP0735018A1

  公开（公告）日：1996-10-02

  There is disclosed an N-(α-alkylbenzylidene)-α-phenylalkylamine represented by the general formula (1): wherein R1 represents a lower alkyl group, R2 represents a hydrogen atom, a halogen atom, a lower alkyl group or a lower alkoxy group and X represents a halogen atom or a lower alkoxy group, its use and a process for producing the same and processes for producing intermediates therefor.

  本发明公开了通式(1)代表的N-(α-烷基亚苄基)-α-苯基烷基胺： 其中 R1 代表低级烷基，R2 代表氢原子、卤素原子、低级烷基或低级烷氧基，X 代表卤素原子或低级烷氧基。
• Verfahren zur Herstellung von racemischen Amino-Derivaten
  申请人：BAYER AG

  公开号：EP0757981A1

  公开（公告）日：1997-02-12

  Nach einem neuen Verfahren lassen sich racemische Amino-Derivate der Formel in welcher R, R1, R2 und n die in der Beschreibung angegebenen Bedeutungen haben, herstellen, indem man optisch aktive Amide der Formel in welcher R1, R2, R3 und n die in der Beschreibung angegebenen Bedeutungen haben, mit starken Basen, gegebenenfalls in Gegenwart eines organischen Verdünnungsmittels umsetzt und gegebenenfalls die dabei entstehenden racemischen Amide entweder a) mit Wasser in Gegenwart einer Base oder einer Säure und gegebenenfalls in Gegenwart eines organischen Verdünnungsmittels umsetzt, oder b) sofern es sich bei den Verbindungen der Formel (Ia) um Amide handelt, in denen R3 für Wasserstoff steht, mit Alkalimetallhydroxid oder Erdalkalimetallhydroxid umsetzt.

  根据一种新方法，外消旋氨基衍生物的化学式为 其中 R、R1、R2 和 n 具有说明中给出的含义、 通过与式中 R、R1、R2 和 n 的光学活性酰胺反应 式中 R1、R2、R3 和 n 的含义见说明、 酌情在有机稀释剂存在下与强碱反应，并酌情使得到的外消旋酰胺 或 a) 在有碱或酸存在的情况下，也可选择在有有机稀释剂存在的情况下，用水、 或 b) 如果式 (Ia) 的化合物是 R3 为氢的酰胺，则与碱金属氢氧化物或碱土金属氢氧化物。
• Synthesis and structure–activity relationships of potential anticonvulsants based on 2-piperidinecarboxylic acid and related pharmacophores
  作者：Bin Ho、A Michael Crider、James P Stables

  DOI：10.1016/s0223-5234(00)01206-x

  日期：2001.3

  Using N-(2,6-dimethyl)phenyl-2-piperidinecarboxamide (1) and N-(alpha -methylbenzyl)-2-piperidinecarboxamide (2) as structural leads, a variety of analogues were synthesised and evaluated for anticonvulsant activity in the MES test in mice. In the N-benzyl series, introduction of 3-Cl, 4-Cl, 3,4-Cl-2, or 3-CF3 groups on the aromatic ring led to an increase in MES activity. Replacement of the alpha -methyl group by either i-Pr or benzyl groups enhanced MES activity with no increase in neurotoxicity. Substitution on the piperidine ring nitrogen led to a decrease in MES activity and neurotoxicity, while reduction of the amide carbonyl led to a complete loss of activity. Movement of the carboxamide group to either the 3- or 4-positions of the piperidine ring decreased MES activity and neurotoxicity. Incorporation of the piperidine ring into a tetrahydroisoquinoline or diazahydrinone nucleus led to increased neurotoxicity. In the N-(2,6-dimethyl)phenyl series, opening of the piperidine ring between the 1- and 6-positions gave the active norleucine derivative 75 (ED50 = 5.8 mg kg(-1), TD50 = 36.4 mg kg(-1), PI = 6.3). Replacement of the piperidine ring of I by cycloalkane (cyclohexane, cyclopentane, and cyclobutane) resulted in compounds with decreased MES activity and neurotoxicity, whereas replacement of the piperidine ring by a 4-pyridyl group led to a retention of MES activity with a comparable PI. Simplification of the 2-piperidinecarboxamide nucleus of 1 into a glycinecarboxamide nucleus led to about a six-fold decrease in MES activity. The 2,6-dimethylanilides were the most potent compounds in the MES test in each group of compounds evaluated, and compounds 50 and 75 should be useful leads in the development of agents for the treatment of tonic-clonic and partial seizures in man. (C) 2001 Editions scientifiques et medicales Elsevier SAS.
• Chiral additive induced self-disproportionation of enantiomers under MPLC conditions: preparation of enantiomerically pure samples of 1-(aryl)ethylamines from racemates
  作者：Mitsuhiro Goto、Kaori Tateishi、Kenki Ebine、Vadim A. Soloshonok、Christian Roussel、Osamu Kitagawa

  DOI：10.1016/j.tetasy.2016.03.004

  日期：2016.5
• Synthesis of 3,4-Dihydroisoquinolines by Cyclization of 1-Bromo-2-(2-isocyanoalkyl)benzenes with Butyllithium
  作者：Kazuhiro Kobayashi、Naoki Matsumoto、Kota Matsumoto

  DOI：10.3987/com-12-12620

  日期：——

  A new and convenient method for the preparation of 3,3-disubstituted 3,4-dihydroisoquinolines has been developed. Thus, the reaction of 1-bromo-2-(bromomethyl)benzenes with (1-isocyano-1-lithioalkyl)benzenes, generated by the treatment of (1-isocyanoalkyl)benzenes with butyllithium, in THF at -78 degrees C gave the corresponding 1-(2-aryl-2-isocyanoalkyl)-2-bromobenzenes, which in turn were transformed into the desired products on treatment with butyllithium in THF at -78 degrees C.