N-苄基-1-(4-溴苯基)甲胺 | 55096-89-4

• 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-苄基-1-(4-溴苯基)甲胺
• 英文名称: N-benzyl-1-(4-bromophenyl)methanamine
• 英文别名: 4-bromodibenzylamine；N-[(4-bromophenyl)methyl]-1-phenylmethanamine
• CAS: 55096-89-4
• 化学式: C₁₄H₁₄BrN
• mdl: MFCD02656614
• 分子量: 276.176
• InChiKey: QXBYDLUZMIWCRP-UHFFFAOYSA-N

物化性质

• 沸点：
  358.3±22.0 °C(Predicted)
• 密度：
  1.328±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2921499090

反应信息

• 作为反应物：
  描述：

  N-苄基-1-(4-溴苯基)甲胺 在 四(三苯基膦)钯 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 三溴化磷 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 6.0h， 生成 benzyl-(4'-bromomethyl-biphenyl-4-ylmethyl)-carbamic acid tert-butyl ester
  参考文献：
  名称：

  A Molecular Plug−Socket Connector

  摘要：

  A monocationic plug-socket connector that is composed, at the molecular level, of three components, (1) a secondary dialkylammonium center (CH2NH2+CH2), which can play the role of a plug toward dibenzo[24]crown-8 (DB24C8), (2) a rigid and conducting biphenyl spacer, and (3) 1,4-benzo-1,5-naphtho[36]crown-10 (BN36C10), capable of playing the role of a socket toward a 4,4'-bipyridinium dicationic plug, was synthesized and displays the ability to act as a plug-socket connector. The fluorescent signal changes associated with the 1,5-dioxynaphthalene unit of its BN36C10 portion were monitored to investigate the association of this plug-socket connector with the complementary socket and plug compounds. The results indicate that (1) the CH2NH2+CH2 part of the molecular connector can thread DB24C8 in a trivial manner and (2) the BN36C10 ring of the connector can be threaded by a 1,1'-dioctyl-4,4'-bipyridinium ion only after the CH2NH2+CH2 site is occupied by a DB24C8 ring. The two connections of the three-component assembly are shown to be controlled reversibly by acid/base and red/ox external inputs, respectively. The results obtained represent a key step for the design and construction of a self-assembling supramolecular system in which the molecular electron source can be connected to the molecular electron drain by a molecular elongation cable.

  DOI：

  10.1021/ja067739e
• 作为产物：
  描述：

  N-苄基-1-(4-溴苯基)甲亚胺 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.0h， 以2.91 g的产率得到N-苄基-1-(4-溴苯基)甲胺
  参考文献：
  名称：

  Discrete multiporphyrin pseudorotaxane assemblies from di- and tetravalent porphyrin building blocks

  摘要：

  两对二价和四价卟啉基团，携带互补超分子冠醚/次级铵离子结合基团，已经被合成，并通过溶液中的NMR光谱和气相中的ESI质谱研究了它们的伪转轮烷衍生物。通过简单混合组分，离散的二聚体和三聚体（金属）卟啉复合物的形成占主导地位，符合结合化学计量学，而替代结构的数量可以忽略不计。我们的结果说明了多价性的强大作用，可以将特定实体的多组分自组装成离散的功能纳米结构。

  DOI：

  10.3762/bjoc.11.85

文献信息

• Homoleptic Bis(trimethylsilyl)amides of Yttrium Complexes Catalyzed Hydroboration Reduction of Amides to Amines
  作者：Pengqing Ye、Yinlin Shao、Xuanzeng Ye、Fangjun Zhang、Renhao Li、Jiani Sun、Beihang Xu、Jiuxi Chen

  DOI：10.1021/acs.orglett.9b04606

  日期：2020.2.21

  Homoleptic lanthanide complex Y[N(TMS)2]3 is an efficient homogeneous catalyst for the hydroboration reduction of secondary amides and tertiary amides to corresponding amines. A series of amides containing different functional groups such as cyano, nitro, and vinyl groups were found to be well-tolerated. This transformation has also been nicely applied to the synthesis of indoles and piribedil. Detailed

  均一的镧系元素络合物Y [N（TMS）2] 3是一种高效的均相催化剂，可用于将硼化的仲酰胺和叔酰胺还原为相应的胺。发现一系列含有不同官能团如氰基，硝基和乙烯基的酰胺具有良好的耐受性。该转化也已经很好地应用于吲哚和吡哌贝地的合成。详细的同位素标记实验，对照实验和动力学研究为阐明反应机理提供了累积的证据。
• Enantioselective Synthesis of α‐Aryl‐β ² ‐Amino‐Esters by Cooperative Isothiourea and Brønsted Acid Catalysis
  作者：Feng Zhao、Chang Shu、Claire M. Young、Cameron Carpenter‐Warren、Alexandra M. Z. Slawin、Andrew D. Smith

  DOI：10.1002/anie.202016220

  日期：2021.5.17

  The synthesis of α‐aryl‐β2‐amino esters through enantioselective aminomethylation of an arylacetic acid ester in high yields and enantioselectivity via cooperative isothiourea and Brønsted acid catalysis is demonstrated. The scope and limitations of this process are explored (25 examples, up to 94 % yield and 96:4 er), with applications to the synthesis of (S)‐Venlafaxine⋅HCl and (S)‐Nakinadine B.

  证明了通过异硫脲和布朗斯台德酸协同催化，对芳基乙酸酯进行对映选择性氨甲基化，以高收率和对映选择性合成α-芳基-β 2 -氨基酯。探索了该过程的范围和局限性（25 个示例，产率高达 94% 和 96:4 er），并应用于 ( S )-文拉法辛·HCl 和 ( S )-Nakinadine B的合成。机理研究是一致的遵循 C(1)-烯醇化铵途径，而不是替代的动态动力学解析过程。对照研究表明 (i) 观察到催化剂和产物 er 之间存在线性效应；(ii)酰基铵离子可以用作预催化剂；（iii）可逆的异硫脲加成到原位生成的亚胺离子上，产生可用作生产性预催化剂的非循环中间体。
• Cobalt(II) Phthalocyanine-Catalyzed Highly Chemoselective Reductive Amination of Carbonyl Compounds in a Green Solvent
  作者：Vishal Kumar、Upendra Sharma、Praveen K. Verma、Neeraj Kumar、Bikram Singh

  DOI：10.1002/adsc.201100645

  日期：2012.3.16

  Cobalt phthalocyanine has been employed for the highly chemoselective reductive amination of aldehydes and ketones in ethanol as a green solvent. A large range of functional groups such as nitro, acid, amide, ester, nitrile, halogen, lactone, methoxy, hydroxy, alkene, N‐benzyl, O‐benzyl and heterocyclic rings were well tolerated under the present reaction conditions.

  酞菁钴已被用于乙醇中作为绿色溶剂的醛和酮的高度化学选择性还原胺化。在目前的反应条件下，对硝基，酸，酰胺，酯，腈，卤素，内酯，甲氧基，羟基，烯烃，N-苄基，O-苄基和杂环等各种官能团的耐受性都很好。
• Expanding the Boundaries of Water-Tolerant Frustrated Lewis Pair Hydrogenation: Enhanced Back Strain in the Lewis Acid Enables the Reductive Amination of Carbonyls
  作者：Éva Dorkó、Márk Szabó、Bianka Kótai、Imre Pápai、Attila Domján、Tibor Soós

  DOI：10.1002/anie.201703591

  日期：2017.8.1

  The development of a boron/nitrogen‐centered frustrated Lewis pair (FLP) with remarkably high water tolerance is presented. As systematic steric tuning of the boron‐based Lewis acid (LA) component revealed, the enhanced back‐strain makes water binding increasingly reversible in the presence of relatively strong base. This advance allows the limits of FLP's hydrogenation to be expanded, as demonstrated

  提出了以硼/氮为中心的失水路易斯对（FLP）的开发，该对具有极高的耐水性。随着对基于硼的路易斯酸（LA）组分的系统空间位阻揭示，增强的反向应变使水结合在存在相对强碱的情况下越来越可逆。这种进步使得FLP氢化的极限得以扩展，正如FLP羰基还原胺化所证明的那样。这种无金属的催化变体显示出广泛的化学选择性和通用性。
• <i>o</i>-Iodoxybenzoic Acid (IBX) as a Viable Reagent in the Manipulation of Nitrogen- and Sulfur-Containing Substrates:  Scope, Generality, and Mechanism of IBX-Mediated Amine Oxidations and Dithiane Deprotections
  作者：K. C. Nicolaou、Casey J. N. Mathison、Tamsyn Montagnon

  DOI：10.1021/ja0400382

  日期：2004.4.28

  o-Iodoxybenzoic acid (IBX), a highly versatile hypervalent iodine(V) reagent, was found to efficiently mediate the dehydrogenation of amines in addition to facilitating the oxidative cleavage of dithioacetals and dithioketals. Through the development of relevant IBX-based protocols, a plethora of useful synthetic intermediates, including imines, oximes, ketones, and aromatic N-heterocycles, were found

  发现邻碘苯甲酸 (IBX) 是一种用途广泛的高价碘 (V) 试剂，除了促进二硫缩醛和二硫缩酮的氧化裂解外，还可以有效介导胺的脱氢。通过开发相关的基于 IBX 的协议，发现大量有用的合成中间体，包括亚胺、肟、酮和芳香族 N-杂环，在特别温和的条件下很容易获得。对这些转化的进一步研究导致了对有价值的机械细节的阐明，从而得出结论，它们是通过离子而不是单电子转移 (SET) 途径进行的。