1-(4-methoxyphenyl)but-3-en-1-amine | 97974-64-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-(4-methoxyphenyl)but-3-en-1-amine
• CAS: 97974-64-6
• 化学式: C₁₁H₁₅NO
• 分子量: 177.246
• InChiKey: WBMRSSYURLNGNH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  35.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  乙醛酸乙酯 、 1-(4-methoxyphenyl)but-3-en-1-amine 以 甲苯 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Development of a 2-Aza-Cope-[3 + 2] Dipolar Cycloaddition Strategy for the Synthesis of Quaternary Proline Scaffolds

  摘要：

  A one-pot multicomponent procedure for the synthesis of highly functionalized pyrrolidine rings through a domino 2-aza-Cope-[3 + 2] dipolar cycloaddition sequence has been demonstrated. This protocol was found to be both high-yielding and stereoselective for the endo cycloadduct.

  DOI：

  10.1021/ol101606v
• 作为产物：
  描述：

  4-甲氧基苯甲醛 在 copper(II) sulfate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 26.0h， 生成 1-(4-methoxyphenyl)but-3-en-1-amine
  参考文献：
  名称：

  Anti-Markovnikov Hydroamination of Homoallylic Amines

  摘要：

  The development of an anti-Markovnikov-selective hydroamination of unactivated alkenes is a significant challenge in organometallic chemistry. Herein, we present the rhodium-catalyzed anti-Markovnikov-selective hydroamination of homoallylic amines. The proximal Lewis basic amine serves to promote reactivity and enforce regioselectivity through the formation of the favored metallacycle, thus over-riding the inherent reactivity of the alkene. The scope of both the amine nudeophiles and homoallylic amines that participate in the reaction is demonstrated.

  DOI：

  10.1021/jacs.5b08500

文献信息

• Controlled Reduction of Nitriles by Sodium Hydride and Zinc Chloride
  作者：Shunsuke Chiba、Derek Yiren Ong

  DOI：10.1055/s-0039-1690838

  日期：2020.5

  new protocol for the controlled reduction of nitriles to aldehydes was developed using a combination of sodium hydride and zinc chloride. The iminyl zinc intermediates derived from aromatic nitriles could be further functionalized with allylmetal nucleophiles to afford homoallylamines. As the method allows the reduction of various aliphatic and aromatic nitriles with a concise procedure under milder

  使用氢化钠和氯化锌的组合，开发了一种控制腈还原为醛的新方案。衍生自芳族腈的亚胺基锌中间体可以用烯丙基金属亲核试剂进一步官能化以提供高烯丙基胺。由于该方法可以在较温和的反应条件下以简明的方法还原各种脂族和芳族腈，并且具有广泛的官能团相容性，因此非常适合用于化学合成中的各种机会。
• α-Aminoallylation of aldehydes in aqueous ammonia
  作者：Shū Kobayashi、Keiichi Hirano、Masaharu Sugiura

  DOI：10.1039/b415264f

  日期：——

  α-Aminoallylation of aldehydes in aqueous ammonia has been developed; commercial aqueous ammonia was successfully used, and this method does not require anhydrous conditions thus leading to easy and practical operations.

  水合氨中醛的α-氨基烯丙基化方法已得到开发；成功使用了商用水合氨，该方法无需无水条件，从而简化了操作，更具实用价值。
• α-Aminoallylation of Aldehydes with Ammonia:  Stereoselective Synthesis of Homoallylic Primary Amines
  作者：Masaharu Sugiura、Keiichi Hirano、Shū Kobayashi

  DOI：10.1021/ja049689o

  日期：2004.6.1

  Three-component reactions of aldehydes, ammonia, and allylboronates were found to provide homoallylic primary amines in high yields with high chemo- and stereoselectivities. A two-step, one-pot, stereoselective synthesis of an uncommon alpha-amino acid, alloisoleucine, was achieved utilizing this reaction.

  发现醛、氨和烯丙基硼酸酯的三组分反应以高产率和高化学和立体选择性提供均烯丙基伯胺。利用该反应实现了一种不常见的 α-氨基酸别异亮氨酸的两步、一锅、立体选择性合成。
• Organometallic reactions in aqueous media. Indium-mediated allylation of sulfonimines
  作者：Tak Hang Chan、Wenshuo Lu

  DOI：10.1016/s0040-4039(98)01926-1

  日期：1998.11

  Barbier-type allylation of sulfonimines with indium and allyl bromide to give homoallylic sulfonamides can be performed smoothly in organic solvents and in aqueous media. The regio- and the stereoselectivity of the reaction have been examined.

  磺胺与铟和烯丙基溴的Barbier型烯丙基化反应可制得均烯丙基磺酰胺，可在有机溶剂和水性介质中平稳进行。已经检查了反应的区域选择性和立体选择性。
• Synthesis of Enantiopure Benzyl Homoallylamines by Indium-Mediated Barbier-Type Allylation Combined with Enzymatic Kinetic Resolution: Towards the Chemoenzymatic Synthesis of N-Containing Heterocycles
  作者：Ari Hietanen、Tiina Saloranta、Sara Rosenberg、Evelina Laitinen、Reko Leino、Liisa T. Kanerva

  DOI：10.1002/ejoc.200901216

  日期：2010.2

  N-(dimethylsulfamoyl)-protected aldimines with a number of allyl bromides followed by high-yielding deprotection afforded allylic amines in good to excellent yields. The racemic amines were then subjected to enzymatic kinetic resolution in order to obtain the corresponding (S)-amines and (R)-amides. When acyl donors with a terminal double bond were applied in the enzymatic kinetic resolution, the product amide

  Barbier 型铟介导的不同 N,N-(二甲基氨磺酰基)-保护的醛亚胺与许多烯丙基溴的烯丙基化，然后进行高产率脱保护，以良好到极好的产率提供烯丙胺。然后对外消旋胺进行酶动力学拆分以获得相应的(S)-胺和(R)-酰胺。当具有末端双键的酰基供体应用于酶动力学拆分时，产物酰胺可以通过闭环复分解以直接的方式转化为不饱和内酰胺。此外，对映体纯的 (S)-1-苯基丁-3-烯胺被转化为相应的二烯丙胺，然后进行闭环复分解以产生模拟许多天然产物的取代脱氢哌啶。