(E)-N-methyl-N-(naphthalen-2-ylmethyl)-3-phenylprop-2-en-1-amine | 98977-54-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (E)-N-methyl-N-(naphthalen-2-ylmethyl)-3-phenylprop-2-en-1-amine
• 英文别名: 2-Naphthalenemethanamine, N-methyl-N-(3-phenyl-2-propenyl)-, (E)-
• CAS: 98977-54-9
• 化学式: C₂₁H₂₁N
• 分子量: 287.404
• InChiKey: OKIUVWRWFRNPAE-JXMROGBWSA-N

物化性质

• 沸点：
  440.1±24.0 °C(Predicted)
• 密度：
  1.082±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 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：

  tert-butyl 3-benzoylazetidine-1-carboxylate 、 (E)-N-methyl-N-(naphthalen-2-ylmethyl)-3-phenylprop-2-en-1-amine 在 4-苯基吡啶 、 双联(2,4-二甲基-2,4-戊二醇)硼酸酯 作用下， 以58 %的产率得到tert-butyl 3-benzoyl-5-((methyl(naphthalen-2-ylmethyl)amino)methyl)-4-phenylpiperidine-1-carboxylate
  参考文献：
  名称：

  硼基自由基催化 (4+2) 环加成反应区域选择性和非对映选择性合成多取代哌啶

  摘要：

  硼基自由基催化的氮杂环丁烷与烯烃的分子间 (4+2) 环加成反应已被开发用于有效合成 3,4,5-多取代哌啶，其含有医学相关的关键杂环基序，并且不易通过其他方法获得。该反应具有模块化程度高、原子经济、操作简单、非金属催化剂廉价、底物范围广泛等特点。

  DOI：

  10.1002/anie.202406612
• 作为产物：
  描述：

  3--1-phenyl-1-propanone 在 盐酸 、 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 2.25h， 生成 (E)-N-methyl-N-(naphthalen-2-ylmethyl)-3-phenylprop-2-en-1-amine
  参考文献：
  名称：

  Synthesis and structure-activity relationships of naftifine-related allylamine antimycotics

  摘要：

  Naftifine (1) is the first representative of the new antifungal allylamine derivatives. Its biological activity is strictly bound to specific structural requirements that are unrelated to those of known antifungals. A tertiary allylamine function seems to be a prerequisite for activity against fungi. By systematic variation of the individual structural elements in 1, detailed structure-activity relationships are defined in which the phenyl ring is the structural feature permitting the widest variations. Versatile synthetic routes to allylamine derivatives and comparative biological data are presented.

  DOI：

  10.1021/jm00151a019

文献信息

• Iridium-catalysed reductive allylic amination of α,β-unsaturated aldehydes
  作者：Liang Liu、Renshi Luo、Jinghui Tong、Jianhua Liao

  DOI：10.1039/d3ob01753b

  日期：——

  unsaturated hydrocarbons have been considered for allylic amination reactions to minimize waste production. Herein, we present an iridium-catalysed method for reductive allylic amination of α,β-unsaturated aldehydes with amines to afford N-allylic amines under air conditions. This protocol is demonstrated to provide products from many substrates (41 examples) in moderate-to-excellent yields. This synthetic

  烯丙基胺化是构建广泛存在于生物活性分子中的N-烯丙基胺的有力工具。一般来说，烯丙醇和不饱和烃已被考虑用于烯丙胺化反应，以尽量减少废物的产生。在此，我们提出了一种铱催化的方法，用于在空气条件下将 α,β-不饱和醛与胺进行还原烯丙基胺化，得到N-烯丙基胺。该方案经证明可以从许多底物（41 个示例）中提供中等至优异产量的产品。这种合成方法还体现在药物分子、光学纯产品的合成以及放大实验上。
• Synthesis and structure-activity relationships of naftifine-related allylamine antimycotics
  作者：Anton Stuetz、Apostolos Georgopoulos、Waltraud Granitzer、Gabor Petranyi、Daniel Berney

  DOI：10.1021/jm00151a019

  日期：1986.1

  Naftifine (1) is the first representative of the new antifungal allylamine derivatives. Its biological activity is strictly bound to specific structural requirements that are unrelated to those of known antifungals. A tertiary allylamine function seems to be a prerequisite for activity against fungi. By systematic variation of the individual structural elements in 1, detailed structure-activity relationships are defined in which the phenyl ring is the structural feature permitting the widest variations. Versatile synthetic routes to allylamine derivatives and comparative biological data are presented.