N-(2-bromo)benzylidene propylamine | 386704-59-2

• 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: N-(2-bromo)benzylidene propylamine
• 英文别名: 1-(2-bromophenyl)-N-propylmethanimine
• CAS: 386704-59-2
• 化学式: C₁₀H₁₂BrN
• 分子量: 226.116
• InChiKey: NXSKVIAJXCZHAO-UHFFFAOYSA-N

物化性质

• 沸点：
  281.9±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)：
  3.28
• 重原子数：
  12.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  12.36
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  N-(2-bromo)benzylidene propylamine 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 4-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 、 邻溴苯甲醛 反应 1.0h， 生成 N-(2-bromo)benzylidene propylamine
  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

• Ortho-Nitro Effect on the Diastereoselective Control in Sulfa-Staudinger and Staudinger Cycloadditions
  作者：Zhanhui Yang、Hassane Abdellaoui、Wei He、Jiaxi Xu

  DOI：10.3390/molecules22050784

  日期：——

  The ortho-nitro effect was discovered in sulfa-Staudinger cycloadditions of ethoxycarbonylsulfene with linear imines. When an ortho-nitro group is present at the C-aryl substituents of linear imines, the sulfa-Staudinger cycloadditions deliver cis-β-sultams in considerable amounts, together with the predominant trans-β-sultams. In other cases, the above sulfa-Staudinger cycloadditions give rise to trans-β-sultams

  在乙氧基羰基亚砜与线性亚胺的磺胺-施陶丁格环加成反应中发现了邻硝基作用。当直链亚胺的C-芳基取代基上存在邻硝基时，磺胺-施陶丁格环加成物将以大量的顺式-β-杜鹃花与主要的反式-β-杜鹃花一起递送。在其他情况下，上述磺胺-施陶丁格环加成仅产生反式-β-杜鹃花。进一步的机械合理化揭示了邻硝基效应归因于其强大的吸电子诱导效应。同样，邻硝基效应也存在于乙氧基羰基乙烯酮与亚胺的斯托丁格环加成中。目前的研究为磺胺-施陶丁格和施陶丁格环加成中的非对映选择性控制提供了进一步的见解。
• Direct access to vicinally functionalized and <i>N</i>-trifluoroacetylated (bicyclic)ketopiperazines using a readily affordable N-heterocyclic anhydride
  作者：Antonio Moreno、Timothy K. Beng

  DOI：10.1039/d0ob00049c

  日期：——

  stereoselective, modular, and chemoselective annulation protocol between a novel N-trifluoroacetyl anhydride and several reactive partners, including lactim ethers, imidoyl chlorides, aryl aldimines, and 1,3-azadienes, leading to vicinally functionalized (bicyclic) 2-piperazinones.

  功能化的2-哌嗪酮通过模拟肽中的反向γ-转角，在构象受限的拟肽中起着至关重要的作用。在这里，我们描述了一种新颖的N-三氟乙酰酐与几种反应性伙伴（包括内酰胺醚，亚氨酰氯，芳基醛亚胺和1,3-氮二烯）之间的有效，可扩展，立体选择性，模块化和化学选择性环合方案，从而实现了病毒功能化（双环）2-哌嗪酮。
• 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。
• 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。
• Steric and Electronic Effects in Capsule-Confined Green Fluorescent Protein Chromophores
  作者：Anthony Baldridge、Shampa R. Samanta、Nithyanandhan Jayaraj、V. Ramamurthy、Laren M. Tolbert

  DOI：10.1021/ja1094606

  日期：2011.2.2

  The turn-on of emission in fluorescent protein chromophores sequestered in an "octaacid" capsule is controlled by stereoelectronic effects described by a linear free energy relationship. The stereochemical effects are governed by both the positions and volumes of the aryl substituents, while the electronic effects, including ortho effects, can be treated with Hammett sigma parameters. The use of substituent volumes rather than A values reflects packing of the molecule within the confines of the capsule.