(E,E)-4-aza-1,5-diphenylpenta-1,3-diene | 119353-37-6

• 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: (E,E)-4-aza-1,5-diphenylpenta-1,3-diene
• 英文别名: (1E,2E)-N-benzyl-3-phenylprop-2-en-1-imine；benzyl-((E)-3-phenylallylidene)amine；N-(cinnamylidene)benzylamine；N-benzylcinnamaldehyde imine
• CAS: 119353-37-6
• 化学式: C₁₆H₁₅N
• 分子量: 221.302
• InChiKey: VMXASONEHFWNLP-LYXWDPSCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.97
• 重原子数：
  17.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  (E,E)-4-aza-1,5-diphenylpenta-1,3-diene 以 四氢呋喃 为溶剂， 反应 2.17h， 生成 dimethyl (2E)-1-[benzyl(chloroacetyl)amino]-3-phenyl-2-propenylphosphonate
  参考文献：
  名称：

  One-Pot Synthesis ofN-Chloroacetyl 1-Aminoalkyl Phosphonates - Precursors of 4-Phosphono-β-Lactams

  摘要：

  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。

  DOI：

  10.1055/s-2005-918440
• 作为产物：
  描述：

  反式肉桂醛 、 苄胺 以 乙醚 为溶剂， 以94%的产率得到(E,E)-4-aza-1,5-diphenylpenta-1,3-diene
  参考文献：
  名称：

  阴离子氨基-Cope重排中不对称诱导的第一个例子

  摘要：

  已经实现了适当官能化的无环3-氨基-1,5-二烯底物的阴离子氨基-Cope重排，并且我们报道了不对称的阴离子氨基-Cope重排产生对映体富集产物（75％ee）的第一个实例。产品的绝对立体化学已得到验证，并提出了过渡态模型以合理化立体化学结果。

  DOI：

  10.1016/s0040-4039(98)00487-0

文献信息

• Diazoketones as precursors in β-lactam synthesis. New insights into the mechanism of the photochemically induced Staudinger reaction
  作者：Michael R. Linder、Wolfgang U. Frey、Joachim Podlech

  DOI：10.1039/b105748k

  日期：2001.10.11

  Diazoketones 1–3, derived from suitably protected amino acids (Ala, Val and Tle), have been photochemically rearranged in the presence of imines leading exclusively to trans-arranged 4-aryl- and cinnamoyl-substituted β-lactams 17–33 with up to 84% yield. Selectivities were dependent on the steric demand of the amino acid side-chain ranging from 65 ∶ 35 to 90 ∶ 10. The relative configurations were proved by several X-ray crystal structures and comparison of NMR spectra. Further reactions of the azetidinones at position C-4 have been performed: electron-rich aryl substituents (e.g., 4-methoxyphenyl, furyl and thienyl) could be degraded to carboxylic acids 34 and 35 which were further transformed to acetoxy derivatives (compounds 36 and 37) in a Kolbe reaction of type II. The cinnamoyl group could be oxidized to the formyl group by ozonolysis (→ 38, 39). The mechanism of the photochemically induced β-lactam formation is discussed in detail.

  从适当保护的氨基酸（Ala、Val和Tle）衍生出的Diazoketones 1–3，在亚胺的存在下通过光化学重排，专一生成了产率高达84%的trans-排列的4-芳基和肉桂酰取代的β-内酰胺17–33。选择性取决于氨基酸侧链的立体需求，范围从65:35到90:10。相对构型通过多个X射线晶体结构和NMR光谱的比较得到了证实。对氮丙啶酮C-4位的进一步反应已经进行：电子富集的芳基取代基（如4-甲氧基苯基、呋喃基和噻吩基）可以降解为羧酸34和35，这些羧酸进一步通过Kolbe II型反应转化为乙酰氧基衍生物（化合物36和37）。肉桂酰基可以通过臭氧分解氧化为醛基（→38, 39）。光化学诱导的β-内酰胺形成机制被详细讨论。
• Molecular Sieves in Ionic Liquids as an Efficient and Recyclable Medium for the Synthesis of Imines
  作者：Carlos Kleber Andrade、Paulo Anselmo Suarez、Sayuri Cristina Takada、Luana Magalhães Alves、Juliana Petrocchi Rodrigues、Rodrigo Fleury Brandão、Valério Cassiano Soares

  DOI：10.1055/s-2004-831328

  日期：——

  A great variety of imines were efficiently isolated in high yields from the reaction of aldehydes and amines in ionic liquids. The ionic liquids could be recovered and reused for at least five cycles without loss in the yields being a useful alternative to dichloromethane or diethyl ether, which are the commonly used solvents for this reaction.

  多种亚胺得以高效地从醛和胺在离子液体中的反应中高产率地分离出来。这些离子液体可被回收并在至少五个循环中重复使用，而产率无明显下降，这为常用的反应溶剂二氯甲烷或乙醚提供了一个有用的替代选择。
• Preparation of homoallylic amines <i>via</i> a three-component coupling process
  作者：Xiaoxu Ou、Ricardo Labes、Claudio Battilocchio、Steven V. Ley

  DOI：10.1039/c8ob01831f

  日期：——

  A three-component synthesis of homoallylic amines is described. The allylboronic species were generated in situ by homologation of vinyl boroxines with trimethylsilyldiazomethane, then followed by trapping of the allylboron intermediate with imines. Twenty-seven compounds were successfully prepared in moderate to high yields. Imines bearing various functional groups were tolerated, including aliphatic

  描述了均烯丙基胺的三组分合成。通过用三甲基甲硅烷基重氮甲烷同价的乙烯基硼氧烷同系物原位产生烯丙基硼物种，然后用亚胺捕获烯丙基硼中间体。以中等至高收率成功制备了27种化合物。容许带有各种官能团的亚胺，包括脂族，芳族和杂芳族取代基。还报道了一些均胺的进一步加工以形成阿西地汀。
• Mg and Zn mediated allylation of imines with allyl bromide
  作者：De-Kun Wang、Li-Xin Dai、Xue-Long Hou、Yi Zhang

  DOI：10.1016/0040-4039(96)00791-5

  日期：1996.6

  Both aldimines and ketimines are allylated under simple Barbier-type conditions using allyl bromide and commercial magnesium foil or zinc dust in tetrahydrofuran at room temperature.

  在简单的Barbier型条件下，室温下使用烯丙基溴和市售的镁箔或锌粉在四氢呋喃中将醛亚胺和酮亚胺烯丙基化。
• The facile synthesis of 1,2,3-trisubstituted pyrroles from the reaction of chlorocarbenes with 1-azabuta-1,3-dienes
  作者：Yuri N. Romashin、Michael T. H. Liu、Roland Bonneau

  DOI：10.1039/a809508f

  日期：——

  1,2,3-Trisubstituted pyrroles have been synthesized in good yield from the reaction of chlorocarbenes with 1-azabuta-1,3-dienes.

  1,2,3-三取代吡咯是由氯代碳与 1-氮杂吲哚-1,3-二烯反应合成的，收率很高。