N-(3-溴苯亚甲基)丙烷-1-胺 | 58646-00-7

• 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-(3-溴苯亚甲基)丙烷-1-胺
• 英文名称: [1-(3-Bromo-phenyl)-meth-(E)-ylidene]-propyl-amine
• 英文别名: (E)-[(3-bromophenyl)methylidene](propyl)amine；1-(3-bromophenyl)-N-propylmethanimine
• CAS: 58646-00-7
• 化学式: C₁₀H₁₂BrN
• 分子量: 226.116
• InChiKey: QCEUSLVMDVPBIA-UHFFFAOYSA-N

物化性质

• 沸点：
  282.8±23.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 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：

  N-(3-溴苯亚甲基)丙烷-1-胺 在 palladium diacetate 、 sodium tetrahydroborate 、 copper diacetate 、 air 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 3.0h， 生成 5-bromo-2-propylisoindolin-1-one
  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 、 间溴苯甲醛 反应 1.0h， 生成 N-(3-溴苯亚甲基)丙烷-1-胺
  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

• Decarboxylative Mannich Reactions with N‐Alkyl Imines
  作者：Marine Pinaud、Leïla Vaïtilingom、Gayathiri Gnanalingam、Tania Xavier、Erwan Le Gall、Marc Presset

  DOI：10.1002/ejoc.202300198

  日期：2023.5.8

  Decarboxylative Mannich reactions with substituted malonic acids half oxyesters as pronucleophiles has been applied to N-alkyl imines. Key to success was the use of an organocatalyst in combination with acid additives to favor the desired pathway. These conditions were also found to be compatible with the in situ generation of the imine, leading to an original multicomponent reaction.

  用取代的丙二酸半氧化酯作为亲核试剂的脱羧曼尼希反应已应用于N-烷基亚胺。成功的关键是将有机催化剂与酸添加剂结合使用以促进所需的途径。还发现这些条件与亚胺的原位生成相容，从而导致原始的多组分反应。
• 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.