2,2-diphenylethylammonium chloride | 7351-52-2

• 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: 2,2-diphenylethylammonium chloride
• 英文别名: 2,2-diphenylethan-1-amine hydrochloride；2,2-diphenylethanaminium chloride；2,2-Diphenylethylamine hydrochloride；2,2-Diphenylethanamine hydrochloride；2,2-diphenylethanamine;hydrochloride
• CAS: 7351-52-2
• 化学式: C₁₄H₁₅N*ClH
• mdl: MFCD02089460
• 分子量: 233.741
• InChiKey: NMKWKTZCPBLCJI-UHFFFAOYSA-N

物化性质

• 熔点：
  253 °C

计算性质

• 辛醇/水分配系数(LogP)：
  2.89
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  27.6
• 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：

  2,2-diphenylethylammonium chloride 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三氟甲磺酸 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (1R,2R,3S,4R,5S)-4-(2-((3-chlorophenyl)ethynyl)-6-(2,2-diphenylethylamino)-9H-purin-9-yl)bicyclo[3.1.0]hexane-2,3-diol
  参考文献：
  名称：

  Truncated Nucleosides as A₃ Adenosine Receptor Ligands: Combined 2-Arylethynyl and Bicyclohexane Substitutions

  摘要：

  C2-Arylethynyladenosine-5'-N-methyluronamides containing a bicyclo[3.1.0]hexane [(N)-methanocarba] ring are selective A(3) adenosine receptor (AR) agonists. Similar 4'-truncated C2-arylethynyl-(N)-methanocarba nucleosides containing alkyl or alkylaryl groups at the N-6 position were low-efficacy agonists or antagonists of the human A(3)AR with high selectivity. Higher hA(3)AR affinity was associated with N-6-methyl and ethyl (K-i = 3-6 nM) than with N-6-arylallcyl groups. However, combined C2-phenylethynyl and N-6-2-phenylethyl substitutions in selective antagonist 15 provided a K-i of 20 nM. Differences between 4'-truncated and nontruncated analogues of extended C2-p-biphenylethynyl substitution suggested a ligand reorientation in AR binding, dominated by bulky N-6 groups in analogues lacking a stabilizing S'-uronamide moiety. Thus, 4'-truncation of C2-arylethynyl-(N)-methanocarba adenosine derivatives is compatible with general preservation of A(3)AR selectivity, especially with small N-6 groups, but reduced efficacy in A(3)AR-induced inhibition of adenylate cyclase.

  DOI：

  10.1021/ml300107e
• 作为产物：
  描述：

  二苯乙腈 在 bis(bis(trimethylsilyl)amido)zinc(II) 、 苯硅烷 、 盐酸 作用下， 以 水 为溶剂， 以80 %的产率得到2,2-diphenylethylammonium chloride
  参考文献：
  名称：

  使用锌前体对腈和叔酰胺进行氢化硅烷化

  摘要：

  我们报告了在无溶剂和温和条件下，由现成的双（六甲基二硅氮基）锌催化的腈和叔酰胺的有效和选择性氢化硅烷化，使其成为现有方法的可持续且理想的替代方案。两种方案均提供高转化率、优异的选择性和广泛的底物范围（从吸电子到供电子和杂环取代）。

  DOI：

  10.1039/d4ob00161c

文献信息

• Boron-Catalyzed Silylative Reduction of Nitriles in Accessing Primary Amines and Imines
  作者：Narasimhulu Gandhamsetty、Jinseong Jeong、Juhyeon Park、Sehoon Park、Sukbok Chang

  DOI：10.1021/acs.joc.5b00941

  日期：2015.7.17

  Silylative reduction of nitriles was studied under transition metal-free conditions by using B(C6F5)3 as a catalyst with hydrosilanes as a reductant. Alkyl and (hetero)aryl nitriles were efficiently converted to primary amines or imines under mild conditions. The choice of silanes was found to determine the selectivity: while a full reduction of nitriles was highly facile, the use of sterically bulky

  在无过渡金属的条件下，通过使用B（C 6 F 5）3作为催化剂，以氢硅烷作为还原剂，研究了腈的甲硅烷基化还原反应。在温和的条件下，烷基和（杂）芳基腈被有效地转化为伯胺或亚胺。发现硅烷的选择决定了选择性：虽然腈的完全还原非常容易，但是使用空间大体积的硅烷允许部分还原，从而生成N-甲硅烷基亚胺。
• Hydrogenation of Nitriles and Ketones Catalyzed by an Air-Stable Bisphosphine Mn(I) Complex
  作者：Stefan Weber、Berthold Stöger、Karl Kirchner

  DOI：10.1021/acs.orglett.8b03132

  日期：2018.11.16

  Efficient hydrogenations of nitriles and ketones with molecular hydrogen catalyzed by a well-defined bench-stable bisphosphine Mn(I) complex are described. These reactions are environmentally benign and atomically economic, implementing an inexpensive, earth-abundant nonprecious metal catalyst. A range of aromatic and aliphatic nitriles and ketones were efficiently converted into primary amines and

  描述了由定义明确的台式稳定双膦Mn（I）配合物催化的分子氢对腈和酮的有效加氢反应。这些反应在环境上是无害的，并且在原子上是经济的，从而实现了廉价的，富含地球的非贵金属催化剂。一系列芳香族和脂肪族腈和酮分别以良好或优异的收率有效地转化为伯胺和醇。腈的氢化反应在100°C下进行，催化剂负载量为2 mol％和20 mol％的碱（t- BuOK），而酮的氢化反应已经在50°C下进行，催化剂负载量为1 mol％和5摩尔％的碱。在两种情况下，均施加50 bar的氢气压力。
• Old Concepts, New Application – Additive‐Free Hydrogenation of Nitriles Catalyzed by an Air Stable Alkyl Mn(I) Complex
  作者：Stefan Weber、Luis F. Veiros、Karl Kirchner

  DOI：10.1002/adsc.201901040

  日期：2019.12.3

  additive-free manganese-catalyzed hydrogenation of nitriles to primary amines with molecular hydrogen is described. The pre-catalyst, a well-defined bench-stable alkyl bisphosphine Mn(I) complex fac-[Mn(dpre)(CO)3(CH3)] (dpre=1,2-bis(di-n-propylphosphino)ethane), undergoes CO migratory insertion into the manganese-alkyl bond to form acyl complexes which upon hydrogenolysis yields the active coordinatively

  描述了一种有效的无添加剂锰催化的分子氢将腈氢化为伯胺的方法。预催化剂，定义明确的台式稳定烷基双膦Mn（I）配合物fac- [Mn（dpre）（CO）3（CH3）]（dpre = 1,2-双（二-正丙基膦基）乙烷），经过CO迁移插入到锰-烷基键中以形成酰基络合物，该络合物经氢解后生成活性的配位不饱和的Mn（I）氢化物催化剂[Mn（dpre）（CO）2（H）]。一系列芳香族和脂肪族腈被有效地和选择性地转化为伯胺，收率良好至极佳。腈的氢化反应在100℃下进行，催化剂负载量为2 mol％，氢气压力为50 bar。通过DFT计算提供了机械方面的见解。
• Synthesis, Characterization, and Catalytic Reactivity of {CoNO}⁸ PCP Pincer Complexes
  作者：Jan Pecak、Wolfgang Eder、Berthold Stöger、Sara Realista、Paulo N. Martinho、Maria José Calhorda、Wolfgang Linert、Karl Kirchner

  DOI：10.1021/acs.organomet.0c00167

  日期：2020.7.27

  reaction of coordinatively unsaturated Co(II) PCP pincer complexes with nitric oxide leads to the formation of new, air-stable, diamagnetic mono nitrosyl compounds. The synthesis and characterization of five- and four-coordinate Co(III) and Co(I) nitrosyl pincer complexes based on three different ligand scaffolds is described. Passing NO through a solution of [Co(PCPNMe-iPr)Cl], [Co(PCPO-iPr)Cl] or

  配位不饱和的Co（II）PCP钳形配合物与一氧化氮的反应导致形成新的，空气稳定的，抗磁性的单亚硝酰基化合物。描述了基于三种不同配体支架的五坐标和四坐标的Co（III）和Co（I）亚硝酰基钳夹配合物的合成和表征。使NO通过[Co（PCP NMe - i Pr）Cl]，[Co（PCP O - i Pr）Cl]或[Co（PCP CH2 - i Pr）Br]溶液导致低自旋形成具有强烈弯曲的NO配体的复合物[Co（PCP- i Pr）（NO）X]。用（X = Cl，Br）AgBF 4处理后一种导致氯化物的提取和形成[Co（PCP- i Pr）（NO）] +类型的带有线性NO基团的阳离子方平面Co（I）配合物。如果将NO计为NO +，则该反应可被视为是金属中心被NO从自由基从Co（III）还原为Co（I）的形式上的两个电子还原。因此，根据Enemark–Feltham约定，这些系统可以描述为CoNO}
• Reusable Nickel Nanoparticles‐Catalyzed Reductive Amination for Selective Synthesis of Primary Amines
  作者：Kathiravan Murugesan、Matthias Beller、Rajenahally V. Jagadeesh

  DOI：10.1002/anie.201812100

  日期：2019.4

  The preparation of nickel nanoparticles as efficient reductive amination catalysts by pyrolysis of in situ generated Ni‐tartaric acid complex on silica is presented. The resulting stable and reusable Ni‐nanocatalyst enables the synthesis of functionalized and structurally diverse primary benzylic, heterocyclic and aliphatic amines starting from inexpensive and readily available carbonyl compounds and

  本文介绍了通过在二氧化硅上热解原位生成的酒石酸络合物来制备作为高效还原胺化催化剂的镍纳米粒子的方法。所得的稳定且可重复使用的镍纳米催化剂能够在分子氢存在下，从廉价且易于获得的羰基化合物和氨开始，合成功能化且结构多样的伯苄基，杂环和脂肪族胺。应用这种基于镍的胺化方案，可以将-NH 2部分引入结构复杂的化合物中，例如，类固醇衍生物和药物。