N,N-dibenzyl-2-methylpropan-1-amine | 121238-79-7

• 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: N,N-dibenzyl-2-methylpropan-1-amine
• 英文别名: Benzenemethanamine, N-(2-methylpropyl)-N-(phenylmethyl)-
• CAS: 121238-79-7
• 化学式: C₁₈H₂₃N
• 分子量: 253.387
• InChiKey: UGSYLMAOWRUPSR-UHFFFAOYSA-N

物化性质

• 沸点：
  132 °C(Press: 0.3 Torr)
• 密度：
  0.987±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N,N-dibenzyl-2-methylpropan-1-amine 、 碘甲烷 生成 dibenzyl-isobutyl-methyl-ammonium; iodide
  参考文献：
  名称：

  Jones, Journal of the Chemical Society, 1903, vol. 83, p. 1419

  摘要：

  DOI：
• 作为产物：
  描述：

  二苄胺 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 苯 为溶剂， 生成 N,N-dibenzyl-2-methylpropan-1-amine
  参考文献：
  名称：

  Katritzky, Alan R.; Yannakopoulou, Konstantina; Lue, Ping, Journal of the Chemical Society. Perkin transactions I, 1989, p. 225 - 233

  摘要：

  DOI：

文献信息

• A General One-Pot, Three-Component Mono N-Alkylation of Amines and Amine Derivatives in Lithium Perchlorate/Diethyl Ether Solution
  作者：Akbar Heydari、Hossein Tavakol、Saied Aslanzadeh、Jamshid Azarnia、Nafiseh Ahmadi

  DOI：10.1055/s-2005-861798

  日期：——

  reductive monoalkyl- ation of amines and amine derivatives with aldehydes is reported. Treatment of aldehydes with primary amines, secondary amines, O- trimethylsilylhydroxylamine, and N,N-dimethylhydrazine in lithi- um perchlorate/diethyl ether and trimethylsilyl chloride, followed by BH3·NEt3 reduction, and straightforward workup afforded sec- ondary amines, tertiary amines, N-substituted hydroxylamines

  报道了一种用醛还原单烷基化胺和胺衍生物的有效通用程序。在高氯酸锂/乙醚和三甲基氯硅烷中用伯胺、仲胺、O-三甲基甲硅烷基羟胺和 N,N-二甲基肼处理醛，然后进行 BH3·NEt3 还原，直接后处理得到仲胺、叔胺，N-取代的羟胺和肼，分别。α-氨基酯与醛的还原烷基化选择性地提供相应的N-单烷基化α-氨基酯。
• Iridium-Catalyzed Alkylation of Amine and Nitrobenzene with Alcohol to Tertiary Amine under Base- and Solvent-Free Conditions
  作者：Chao Li、Ke-feng Wan、Fu-ya Guo、Qian-hui Wu、Mao-lin Yuan、Rui-xiang Li、Hai-yan Fu、Xue-li Zheng、Hua Chen

  DOI：10.1021/acs.joc.8b03137

  日期：2019.2.15

  and green method for the selective synthesis of tertiary amines has been developed that involves iridium-catalyzed alkylation of various primary amines with aromatic or aliphatic alcohols. Notably, the catalytic protocol enables this transformation in the absence of additional base and solvent. Furthermore, the alkylation of nitrobenzene with primary alcohol to tertiary amine has also been achieved by

  在此，已经开发了一种用于选择性合成叔胺的有效且绿色的方法，该方法涉及用芳族或脂族醇进行的铱催化的各种伯胺的烷基化。值得注意的是，催化方案能够在不存在额外的碱和溶剂的情况下实现这种转化。此外，硝基苯与伯醇烷基化为叔胺也已通过相同的催化体系实现。进行了氘标记实验和一系列对照实验，结果表明在烷基化过程中可能存在分子间借氢途径。
• Reduction of amides to amines via catalytic hydrosilylation by a rhodium complex
  作者：Ryoichi Kuwano、Masatoshi Takahashi、Yoshihiko Ito

  DOI：10.1016/s0040-4039(97)10804-8

  日期：1998.2

  Reduction of a wide range of tertiary amides with 2 molar equivalents of diphenylsilane was promoted by 0.1 mol% of RhH(CO)(PPh3)3 at room temperature, affording the corresponding tertiary amines in high yields. The synthetic utility is demonstrated by chemoselective reductions of amides having functional groups such as ester and epoxy groups which are not tolerated by the conventional reductions with

  在室温下，通过0.1摩尔％的RhH（CO）（PPh 3）3促进使用2摩尔当量的二苯基硅烷还原各种叔酰胺，从而以高收率提供相应的叔胺。通过化学选择性还原具有官能团如酯和环氧基团的酰胺的化学选择还原证明了常规的用LiAlH 4和BH 3的还原不能耐受的酰胺。
• Aminomethylation of organic halides promoted by zinc in protic medium
  作者：Idália H.S. Estevam、Margarete F. da Silva、Lothar W. Bieber

  DOI：10.1016/j.tetlet.2005.08.139

  日期：2005.10

  halides undergo smooth aminomethylation by secondary amines and aqueous formaldehyde promoted by metallic zinc under copper(I) catalysis. Good to excellent yields are obtained with primary, secondary, and tertiary iodides, allylic, propargylic, and benzylic bromides and with α-bromoesters. In most cases, DMSO is the best solvent, but dioxane is preferable for some more reactive halides. Additional experiments

  在铜（I）催化下，有机卤化物可通过仲胺和甲醛水溶液（由金属锌促进）进行平滑的氨甲基化反应。用伯，仲和叔碘化物，烯丙基，炔丙基和苄基溴化物以及α-溴代酸酯可获得良好或优异的收率。在大多数情况下，DMSO是最好的溶剂，但对于一些更具活性的卤化物，二恶烷是优选的。使用自由基猝灭剂和促进剂的其他实验以及“自由基钟”的使用表明，逐步反应机理是由烷基自由基攻击亚胺离子引发的。
• “One pot” synthesis of tertiary amines: Ru(II) catalyzed direct reductive N -benzylation of imines with benzyl bromide derivatives
  作者：Bin Li、Jinghao Yu、Caihua Li、Yibiao Li、Jianli Luo、Yan Shao

  DOI：10.1016/j.tetlet.2016.11.112

  日期：2017.1

  The direct reductive N-benzylation of imines by reaction with benzyl bromide derivatives, in the presence of [RuCl2(p-cymene)]2 catalyst and PhSiH3, is performed under mild conditions without additional base. This reaction proceeds by a tandem imine hydrosilylation/nucleophilic substitution with benzyl bromide derivatives to result the tertiary amines.

  在[RuCl 2（p- cymene）] 2催化剂和PhSiH 3的存在下，通过与苄基溴衍生物反应，使亚胺直接还原N-苄基化反应是在温和的条件下进行的，无需额外的碱。该反应通过用亚苄基溴衍生物进行串联的亚胺氢化硅烷化/亲核取代而进行，从而得到叔胺。