2-(4-chlorophenyl)-N,N-dimethylethanamine | 2736-31-4

• 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: 2-(4-chlorophenyl)-N,N-dimethylethanamine
• 英文别名: 1-Dimethylamino-2-p-chlorphenylethan；Chloro-N.N-dimethylphenaethylamin；Dimethyl-2--aethyl-amin；N,N-Dimethyl-2-(4-chlorophenyl)ethylamine
• CAS: 2736-31-4
• 化学式: C₁₀H₁₄ClN
• mdl: MFCD25961810
• 分子量: 183.681
• InChiKey: RKLSNRMANRTWPZ-UHFFFAOYSA-N

物化性质

• 沸点：
  240.9±23.0 °C(Predicted)
• 密度：
  1.052±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(4-chlorophenyl)-N,N-dimethylethanamine 、 苯乙炔 在 叔丁基过氧化氢 、 copper(ll) bromide 作用下， 以 乙腈 为溶剂， 反应 6.0h， 以48%的产率得到N-(4-chlorophenethyl)-N-methyl-3-phenylprop-2-yn-1-amine
  参考文献：
  名称：

  CuBr2 催化叔甲胺与末端炔烃在温和条件下使用 TBHP 水溶液进行炔基化反应

  摘要：

  已经开发了一种 CuBr 2催化的叔甲胺与末端炔烃的炔基化反应。与最近主要集中在芳族甲胺的烯基化反应相比，这种转化对脂肪族叔甲胺表现出良好的反应性。反应在室温下使用 TBHP 水溶液进行，无需惰性气氛。

  DOI：

  10.1016/j.tetlet.2022.154136
• 作为产物：
  描述：

  4-氯苯乙胺 生成 2-(4-chlorophenyl)-N,N-dimethylethanamine
  参考文献：
  名称：

  Smith,J.R.L. et al., Journal of the Chemical Society. Perkin transactions I, 1972, p. 228 - 233

  摘要：

  DOI：

文献信息

• Isotope Effect Studies on Elimination Reactions. IX. The Nature of the Transition State for the E2 Reaction of 2-Arylethylammonium Ions with Ethoxide in Ethanol
  作者：P. J. Smith、A. N. Bourns

  DOI：10.1139/v74-118

  日期：1974.3.1

  Kinetic isotope effects have been determined for the E2 reaction of some 2-arylethyltrimethyl-ammonium ions with ethoxide in ethanol at 40°. The nitrogen effect, (k14/k15 − 1)100, decreased with increasing electron-withdrawing ability of the para substituent; i.e. 1.37, 1.33, 1.14, and 0.88 for p-OCH3, p-H, p-Cl, and p-CF3, respectively. Furthermore, the primary hydrogen–deuterium isotope effects increased

  已确定某些 2-芳乙基三甲基铵离子与乙醇在 40° 下的 E2 反应的动力学同位素效应。氮效应，(k14/k15 − 1)100，随着对位取代基吸电子能力的增加而降低；即 p-OCH3、pH、p-Cl 和 p-CF3 分别为 1.37、1.33、1.14 和 0.88。此外，对于相同的取代基，主要的氢-氘同位素效应分别增加；即 kH/kD = 2.64、3.23、3.48 和 4.16。发现 3.66 的大正 ρ 值以及 1.02 的小的二次 α-氘效应对 pH 值。此外，随着乙基三甲基铵离子反应的提取碱强度的增加，氮同位素效应减弱；即与 EtO--EtOH 和 t-BuO--t-BuOH 反应在 60° 时分别为 1.86 和 1.41。
• Dimethylamination of Primary Alcohols Using a Homogeneous Iridium Catalyst: A Synthetic Method for <i>N</i>,<i>N</i>-Dimethylamine Derivatives
  作者：Jaeyoung Jeong、Ken-ichi Fujita

  DOI：10.1021/acs.joc.0c02896

  日期：2021.3.5

  alcohols using aqueous dimethylamine in the absence of additional organic solvents has been developed. The reaction proceeds via borrowing hydrogen processes, which are atom-efficient and environmentally benign. An iridium catalyst bearing an N-heterocyclic carbene (NHC) ligand exhibited high performance, without showing any deactivation under aqueous conditions. In addition, valuable N,N-dimethylamine

  已经开发了在不存在其他有机溶剂的情况下使用二甲胺水溶液进行伯醇的N，N-二甲基氨基化的新催化系统。该反应通过借用氢过程进行，该过程是原子有效的且对环境无害。带有N-杂环卡宾（NHC）配体的铱催化剂表现出高性能，而在水性条件下没有任何失活。另外，合成了有价值的N，N-二甲基胺衍生物，包括生物活性分子和药物分子。这种方法的实际应用已通过克级反应得到了证明。
• A convenient synthesis of o-methylbenzylamine derivatives from benzyl halides: the improved Sommelet–Hauser rearrangement
  作者：Mitsuji Nakano、Yoshiro Sato

  DOI：10.1039/c39850001684

  日期：——

  Desilylation by fluoride anion of benzyldimethyl(trimethylsilylmethyl)ammonium halides having a Cl–, CN–, or AcO– substituent on the benzene ring gave high yields of the Sommelet–Hauser rearrangement products at room temperature.

  由具有氯苄基二甲基（三甲基甲硅烷）卤化铵的氟阴离子脱甲硅烷基-，CN - ，或ACO -在苯环上的取代基，得到Sommelet-Hauser重排反应产物在室温下的高的产率。
• 8-OXODIHYDROPURINE DERIVATIVE
  申请人：Aachi Keiji

  公开号：US20120172347A1

  公开（公告）日：2012-07-05

  The present invention provides a compound represented by the formula (1) or a pharmaceutically acceptable salt thereof (wherein W represents a hydrogen atom, a halogen atom, or the others; A represents an alkyl group optionally substituted by aryl group or the others, an aryl group, or the others; and one of X and Y represents a di-substituted alkylaminocarbonyl group, or the others, and the other represents a hydrogen atom, an alkyl group, an alkylcarbonyl group, or the others); a medicament or a pharmaceutical composition for treatment or prophylaxis of FAAH-related diseases such as depression, anxiety disorder or pains, comprising the compound or the like as an active ingredient; a use of the compound or the like; and a method for treatment or prophylaxis using the compound or the like.

  本发明提供一种由式（1）表示的化合物或其药用可接受的盐（其中W代表氢原子、卤素原子或其他；A代表可选地被芳基取代的烷基基团或其他、芳基团或其他；X和Y中的一个代表二取代的烷基氨基羰基团或其他，另一个代表氢原子、烷基基团、烷基羰基团或其他）；一种治疗或预防FAAH相关疾病如抑郁症、焦虑症或疼痛的药物或药物组合物，包括该化合物或类似物作为活性成分；一种使用该化合物或类似物的用途；以及使用该化合物或类似物的治疗或预防方法。
• Structure–activity correlations for β-phenethylamines at human trace amine receptor 1
  作者：Anita H. Lewin、Hernán A. Navarro、S. Wayne Mascarella

  DOI：10.1016/j.bmc.2008.06.009

  日期：2008.8

  A cell line in which RD-HGA16 cells were stably transfected with the hTAAR 1 receptor was created and utilized to carry out a systematic evaluation of a series of beta-phenethylamines. Fair agreement was observed with data obtained for aryl and ethylene chain substituted analogs in an AV12-664 cell line in which hemagglutinin-tagged hTAAR 1 was stably co-expressed with rat Gas. Analogs with multiple substituents as well as analogs with bulky groups were found to be partial agonists. Analogs in which the primary amino group was converted to a secondary or a tertiary amino group by N-methylation were also partial agonists. Comparative Molecular Field Analysis (CoMFA) using the potency data yielded a regression coefficient r(2) of 0.824. The steric field contribution to the model was 61% with the balance (39%) contributed by the electrostatic field. The collective results suggest that increasing steric bulk both at the amino nitrogen, particularly by N-dimethylation, and at the 4-position of the aromatic ring leads to low efficacy ligands. (C) 2008 Elsevier Ltd. All rights reserved.