[1-(3-Chloro-phenyl)-meth-(E)-ylidene]-propyl-amine | 1032080-61-7

• 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-(3-Chloro-phenyl)-meth-(E)-ylidene]-propyl-amine
• 英文别名: 1-(3-chlorophenyl)-N-propylmethanimine
• CAS: 1032080-61-7
• 化学式: C₁₀H₁₂ClN
• 分子量: 181.665
• InChiKey: DMQRCGUHWWCLAO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  12.4
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  [1-(3-Chloro-phenyl)-meth-(E)-ylidene]-propyl-amine 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以1.78 g的产率得到3-氯-N-丙基-苯甲胺
  参考文献：
  名称：

  Preparation of Benzolactams by Pd(OAc)₂-Catalyzed Direct Aromatic Carbonylation

  摘要：

  We developed a new method for Pd(II)-catalyzed direct aromatic carbonylation in a phosphine-free catalytic system using Pd(OAc)2 and Cu(OAc)2 in an atmosphere of CO gas containing air. The carbonylation proceeded with ortho-palladation, inducing a remarkable site selectivity to afford a variety of five- or six-membered benzolactams from secondary omega-arylalkylamines, such as N-alkylbenzylamines or N-alkylphenethylamines.

  DOI：

  10.1021/ja045342+
• 作为产物：
  描述：

  正丙胺 、 3-氯苯甲醛 反应 1.0h， 生成 [1-(3-Chloro-phenyl)-meth-(E)-ylidene]-propyl-amine
  参考文献：
  名称：

  限制条件下揭示的GFP型发色团中的潜在反应：邻-卤代苯并亚苄基-3-甲基咪唑啉酮经电化过程的光羟基化

  摘要：

  在乙腈溶液中以及在辛酸胶囊在水中提供的密闭环境中，研究了卤素取代的GFP型发色团的激发态行为。在邻位，间位和对位卤素取代的GFP生色团中，仅邻位化合物会产生新产物，这是由于卤素通过羟基空前的光解而产生的。这种不寻常的反应凸显了密闭空间在实现某些无法实现的光反应中的重要性。

  DOI：

  10.1021/ol5013058

文献信息

• Antimykobakterielle 1-Phenyl-1-alkylaminoalkane
  作者：Wolfgang Meindl

  DOI：10.1002/ardp.19933260506

  日期：——

  wird die Synthese und die Prüfung auf antimykobakterielle Eigenschaften (M. tuberculosis H 37 Ra, Middlebrook‐7H9‐Nährlösung) von 1‐Phenyl‐1‐alkylaminoalkanen, die sich von antimykobakteriellen N‐Alkylbenzylaminen durch eine zusätzliche Alkylgruppe in α‐Stellung unterscheiden. Durch Variation beider Alkylketten und Ringsubstitution mit 1 oder 2 Cl‐Atomen steigt die Wirksamkeit bis zu einem Optimum innerhalb

  描述了 1-苯基-1-烷基氨基烷烃的抗分枝杆菌特性（结核分枝杆菌 H 37 Ra，Middlebrook-7H9 营养液）的合成和测试，其与抗分枝杆菌 N-烷基苄胺的不同之处在于 α 位有一个额外的烷基。通过用 1 或 2 个 Cl 原子改变烷基链和环取代，效​​率增加到同源系列内的最佳状态。超过最佳亲脂性和烷基链支化会降低活性。
• Mannich‐Type Reactions of Alkylzinc Reagents
  作者：Marine Pinaud、Emilie Plantiveau、Eric Huet、Erwan Le Gall、Marc Presset

  DOI：10.1002/ejoc.202300572

  日期：2023.8.21

  The addition of alkylzinc halides to imines has been studied under different conditions. Whereas Mannich-type reactions with sulfonyl imines occurs upon simple heating, the use N-alkyl imines required an additional activation: the use of acetyl chloride led to the preparation of N-acyl tertiary amines whereas trimethylsilyl chloride afforded a direct access to unprotected secondary amines.

  在不同条件下研究了烷基卤化锌与亚胺的加成反应。虽然与磺酰亚胺的曼尼希型反应在简单加热时发生，但使用N-烷基亚胺需要额外的活化：使用乙酰氯导致制备N-酰基叔胺，而三甲基氯硅烷可直接获得未保护的仲胺。
• Benzylamines: synthesis and evaluation of antimycobacterial properties
  作者：Wolfgang R. Meindl、Erwin Von Angerer、Helmut Schoenenberger、Gotthard Ruckdeschel

  DOI：10.1021/jm00375a005

  日期：1984.9

  The synthesis of benzylamines with various N-alkyl chains and substituents in the aromatic system as well as their evaluation on Mycobacterium tuberculosis H 37 Ra are described. The most active compounds in this test, N-methyl-3-chlorobenzylamine (19, MIC 10.2 micrograms/mL), N-methyl-3,5-dichlorobenzylamine (93, MIC 10.2 micrograms/mL), and N-butyl-3,5-difluorobenzylamine (103, MIC 6.4 micrograms/mL), also exhibited a marked inhibitory effect on Mycobacterium marinum and Mycobacterium lufu used for the determination of antileprotic properties. The combinations of 93 with aminosalicylic acid, streptomycin, or dapsone exert marked supra-additive effects on M. tuberculosis H 37 Ra.
• Separation of Ring Polar and Resonance Effects on the Rate Constants for Uncatalyzed N-Arylidenepropylamine Formation in Methanol
  作者：Jean Toullec、Didier Milin

  DOI：10.1021/jo00089a033

  日期：1994.5

  Rate constants are reported for the reaction of a series of 19 ring-substituted benzaldehydes with propylamine in methanol and in O-d-methanol at different temperatures and of three of them with 2-methoxyethylamine and 2,2-dimethoxyethylamine. The large direct solvent kinetic isotope effects (KSIE) (2.1-2.9), as well as the Delta H* (4.7-7.6 kcal mol(-1)) values vary smoothly with substituent. Delta S* (ca. -45 cal mol(-1) K-1) is almost independent of substituent. These data indicate that there in no change in the rate-limiting step, and since the large KSIE and \Delta S*\ can be related to significant solvation of the leading OH- group at the transition state, they agree with a mechanism involving cu-amino alcohol formation in a fast preequilibrium followed by rate-limiting OH- detachment yielding iminium ions. When corrected for parallel hemiacetal formation, the second-order rate constants are accounted for by the Young-Jencks equation with p(n) = 0.08 and p(r) = 0.57, this equation allowing a separation of the direct resonance effects from the polar effects of the substituted ring. The very low p(n) value indicates that the polar effects for the rate-limiting OH- detachment are almost compensated by those on the constant of the alpha-amino alcohol-formation preequilibrium. In contrast, the relatively large p(r) coefficient, which means that the overall rate constants depend almost exclusively on resonance, is due to predominance of the direct resonance effects on the preequilibrium. The KSIE and Delta S* data, as well as the beta(nucl) parameters (close to unity) observed when the reacting amine was changed (slopes of the straight lines obtained by plotting the logarithm of the rate constants vs the pK(a) of the ammonium ions) favor a late transition state. In contrast, the low p(r) value for the rate-limiting step (ca. -0.5) shows that the transition state is not iminium ion-like.
• Synthesis and SAR of 1,2,3,4-tetrahydroisoquinolin-1-ones as novel G-protein-coupled receptor 40 (GPR40) antagonists
  作者：Paul S. Humphries、John W. Benbow、Paul D. Bonin、David Boyer、Shawn D. Doran、Richard K. Frisbie、David W. Piotrowski、Gayatri Balan、Bruce M. Bechle、Edward L. Conn、Kenneth J. Dirico、Robert M. Oliver、Walter C. Soeller、James A. Southers、Xiaojing Yang

  DOI：10.1016/j.bmcl.2009.03.082

  日期：2009.5

  The development of a series of novel 1,2,3,4-tetrahydroisoquinolin-1-ones as antagonists of G protein-coupled receptor 40 (GPR40) is described. The synthesis, in vitro inhibitory values for GPR40, in vitro microsomal clearance and rat in vivo clearance data are discussed. Initial hits displayed high rat in vivo clearances that were higher than liver blood flow. Optimization of rat in vivo clearance was achieved and led to the identification of 15i, whose rat oral pharmacokinetic data is reported. (c) 2009 Elsevier Ltd. All rights reserved.