N-benzyl-2-methylpropan-1-imine | 22483-21-2

• 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-benzyl-2-methylpropan-1-imine
• 英文别名: E-2-methylpropanal N-benzylimine；(E)-N-(2-methylpropylidene)-1-phenylmethanamine；(E)-N-benzyl-2-methylpropan-1-imine；N-(2-methylpropylidene)benzylamine；N-isobutylidene-benzylamine；isobutylidenebenzylamine
• CAS: 22483-21-2
• 化学式: C₁₁H₁₅N
• 分子量: 161.247
• InChiKey: RBDNYMZMECTVGV-XYOKQWHBSA-N

物化性质

• 沸点：
  105 °C(Press: 15 Torr)
• 密度：
  0.9288 g/cm3(Temp: 4 °C)

计算性质

• 辛醇/水分配系数(LogP)：
  2.91
• 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：
  0.36
• 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-benzyl-2-methylpropan-1-imine 在 titanocene dichloride 、 正丁基氯化镁 作用下， 以 乙醚 为溶剂， 反应 15.0h， 以92%的产率得到N-苄基-2-甲基-1-丙胺
  参考文献：
  名称：

  Reduction of Imines via Titanium-Catalyzed Hydromagnesation

  摘要：

  We have recently discovered that imines can be reduced to amines via a titanium catalyzed hydromagnesation reaction. These reactions employ n-BuMgCl (1.2 eq) as the stoichiometric reducing agent and Cp2TiCl2 (3-5 mol%) as a catalyst. Reactions are run under nitrogen at ambient temperature and pressure. For most aldimine and cyclic ketimine substrates amine products are obtained in yields ranging from 69-94%. The reaction is not tolerant of bulky nitrogen substituents or primary enolizable protons on the imine substrate. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01797-8
• 作为产物：
  描述：

  2-benzoyl-N-benzyl-2-methylpropanimine 生成 N-benzyl-2-methylpropan-1-imine
  参考文献：
  名称：

  ARMESTO, D.;RAMOS, A.;PEREZ-OSSORIO, R., TETRAHEDRON LETT., 1982, 23, N 49, 5195-5198

  摘要：

  DOI：

文献信息

• N,Se-Acetals: Preparation and use in diastereoselective radical reactions
  作者：Aleksandar Stojanovic、Philippe Renaud

  DOI：10.1002/hlca.19980810216

  日期：1998.2.4

  3–5). These acetals are used as precursors for stereoselective radical deuteration and allylation reactions (Schemes 6 and 7, Tables 1 and 2). The stereochemical outcome of the reactions depends on the radical trap and the substituents at the N-atom. Deuterations give always anti products with moderate to high selectivities. The allylation reactions give either syn or anti products with low to moderate

  提出了一种新的简便的从醛和伯胺开始合成N，S-和N，Se-乙缩醛的方法（方案3-5）。这些缩醛用作立体选择性自由基氘化和烯丙基化反应的前体（方案6和7，表1和2）。反应的立体化学结果取决于自由基陷阱和N原子上的取代基。氘代化合物始终会产生具有中等至高选择性的抗产物。烯丙基化反应产生具有低到中等选择性的顺式或反式产物。观察到的立体选择性可以用基于最小化A 1,3的模型来解释 并受空间和立体电子效应控制。
• One-Pot Synthesis of<i>N</i>-Chloroacetyl 1-Aminoalkyl Phosphonates - Precursors of 4-Phosphono-β-Lactams
  作者：Christian V. Stevens、Kristof Moonen

  DOI：10.1055/s-2005-918440

  日期：——

  4-Phosphono-β-lactams are synthesized via a three-step sequence, including final formation of the C3-C4 bond through a phosphorus-stabilized carbanion. The chlorinated precursors can be synthesized via two different methods: a one-pot N-acylation of an aromatic imine followed by addition of a trialkyl phosphite or phosphonylation of a suitable imine followed by N-acylation in a separate reaction step. The former method was preferred because of the ease of the reaction and the good yields obtained.

  4-膦酰基-β-内酰胺通过三步序列合成，其中包括通过磷稳定的碳负离子形成C3-C4键。氯化前体可以通过两种不同方法合成：一种是将芳香亚胺进行N-酰化，然后加入三烷基亚磷酸酯或通过先对合适亚胺进行膦酰化再进行独立反应步骤中的N-酰化。前者方法更受欢迎，因为反应简便且产率高。
• Direct Synthesis of Pyrroles from Imines, Alkynes, and Acid Chlorides:  An Isocyanide-Mediated Reaction
  作者：Daniel J. St. Cyr、Nicolas Martin、Bruce A. Arndtsen

  DOI：10.1021/ol062773j

  日期：2007.2.1

  [reaction: see text] A direct synthesis of pyrroles from imines, acid chlorides, and alkynes mediated by isocyanides is reported. This reaction proceeds with a range of each of these three substrates, providing a method to generate families of pyrroles in high yield. Mechanistic studies suggest this process proceeds via the generation of imino analogues of munchnones, which can undergo in situ coupling

  [反应：见正文]据报道，由亚胺，亚胺，酰氯和炔烃直接合成吡咯是由异氰化物介导的。该反应在这三种底物的一定范围内进行，从而提供了一种以高收率产生吡咯家族的方法。机理研究表明，该过程是通过生成长棍素的亚氨基类似物来进行的，其可以与炔烃进行原位偶联以释放异氰酸酯并形成吡咯产物。
• Direct Preparation of Allylic Zirconium Reagents from Zirconocene−Olefin Complexes and Alkenes
  作者：Kazuya Fujita、Hideki Yorimitsu、Hiroshi Shinokubo、Koichiro Oshima

  DOI：10.1021/jo049863r

  日期：2004.5.1

  for preparation of allylic zirconium reagents directly from 1-alkenes via zirconocene−olefin complex has been developed. Selective transfer of the hydride of zirconocene allyl hydride complex, a tautomer of zirconocene−olefin complex, to diisopropyl ketone generates the corresponding zirconocene alkoxide allyl. The allylic zirconium reagents formed effects stereoselective allylation of aldehyde at 25

  已开发出一种新的方法，可通过锆茂-烯烃复合物直接从1-烯烃制备烯丙基锆试剂。锆茂-烯络合物的互变异构体锆茂烯丙基氢化物配合物的氢化物选择性转移至二异丙基酮，生成相应的锆茂烯醇盐烯丙基。形成的烯丙基锆试剂在25°C和-78°C下实现醛的立体选择性烯丙基化，分别提供顺式和反式均烯丙基醇。该反式异构体是通过动力学控制下的六元椅过渡态形成。该SYN -选择性可以通过考虑异构化合理化反被retroallylation过程-adduct。
• Structure-Based Analysis and Optimization of a Highly Enantioselective Catalyst for the Strecker Reaction
  作者：Petr Vachal、Eric N. Jacobsen

  DOI：10.1021/ja027246j

  日期：2002.8.1

  asymmetric Strecker reaction catalyzed by a metal-free Schiff base catalyst was conducted. The active site of the catalyst, the relevant stereoisomer of the imine substrate, and the solution structure of the imine-catalyst complex were elucidated using a series of kinetics, structure-activity, and NMR experiments. An unusual bridging interaction between the imine and the urea hydrogens of the catalyst was

  进行了由无金属 Schiff 碱催化剂催化的不对称 Strecker 反应的机理研究。使用一系列动力学、结构-活性和核磁共振实验阐明了催化剂的活性位点、亚胺底物的相关立体异构体以及亚胺-催化剂复合物的溶液结构。亚胺和催化剂的尿素氢之间不寻常的桥连相互作用被确定并通过计算得到支持。基于机理洞察的催化剂结构的合理优化导致了不对称 Strecker 反应的改进催化剂。