(2S)-1-(4-methoxyphenyl)but-3-en-2-amine | 1163716-52-6

• 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: (2S)-1-(4-methoxyphenyl)but-3-en-2-amine
• 英文别名: (S)-1-(4-methoxybenzyl)allylamine
• CAS: 1163716-52-6
• 化学式: C₁₁H₁₅NO
• 分子量: 177.246
• InChiKey: FHLQMCAFYGBUJG-SNVBAGLBSA-N

物化性质

• 沸点：
  288.2±25.0 °C(Predicted)
• 密度：
  0.993±0.06 g/cm3(Predicted)

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：

  (2S)-1-(4-methoxyphenyl)but-3-en-2-amine 在 四氢吡咯 、 吡啶 、 甲醇 、 sodium tetrahydroborate 、 二甲基硫 、 camphor-10-sulfonic acid 、 三乙酰氧基硼氢化钠 、 臭氧 、 magnesium 、 溶剂黄146 、 三乙胺 、 lithium hexamethyldisilazane 、 三氯氧磷 、 原甲酸三甲酯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙酸乙酯 、 乙腈 为溶剂， 反应 184.0h， 生成 (5S,6R,7R,10aR)-8-{[tert-butyl(dimethyl)silyl]oxy}-6-hydroxy-5-(4-methoxybenzyl)octahydro-3H-7,10a-methanopyrrolo[1,2-a]azocin-3-one
  参考文献：
  名称：

  STEREOCONTROLLED TOTAL SYNTHESIS OF (−)-FR901483

  摘要：

  The total synthesis of a potent immunosuppressant (-)-FR901483 is accomplished. The skeleton itself is constructed by the Ugi 4CC reaction, subsequent intramolecular Dieckmann condensation, and a diastereoselective intramolecular aldol reaction. However, the remarkable feature is the stereoselective incorporation of the p-methoxybenzyl and methylamino groups within the tricyclic core skeleton.

  DOI：

  10.3987/com-12-s(n)38
• 作为产物：
  描述：

  tert-butyl (S)-(4-chloro-1-(4-methoxyphenyl)-3-oxobutan-2-yl)carbamate 在 盐酸 、 sodium tetrahydroborate 、 potassium thioacyanate 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 为溶剂， 反应 60.0h， 生成 (2S)-1-(4-methoxyphenyl)but-3-en-2-amine
  参考文献：
  名称：

  STEREOCONTROLLED TOTAL SYNTHESIS OF (−)-FR901483

  摘要：

  The total synthesis of a potent immunosuppressant (-)-FR901483 is accomplished. The skeleton itself is constructed by the Ugi 4CC reaction, subsequent intramolecular Dieckmann condensation, and a diastereoselective intramolecular aldol reaction. However, the remarkable feature is the stereoselective incorporation of the p-methoxybenzyl and methylamino groups within the tricyclic core skeleton.

  DOI：

  10.3987/com-12-s(n)38

文献信息

• Synthesis of the optically active key intermediate of FR901483
  作者：Shigeru Ieda、Toshiyuki Kan、Tohru Fukuyama

  DOI：10.1016/j.tetlet.2010.05.089

  日期：2010.8

  Efficient synthesis of the tricyclic key intermediate 2 for (−)-FR901483 1 was accomplished. The precursor of the intramolecular aldol reaction 4b is constructed by the Ugi 4CC reaction and subsequent intramolecular Dieckmann condensation. This approach allows a fully stereocontrolled total synthesis of (−)-FR901483, which would provide various derivatives.

  有效合成了（-）-FR901483 1的三环键中间体2。分子内醛醇缩合反应4b的前体通过Ugi 4CC反应和随后的分子内狄克曼缩合来构建。这种方法允许（-）-FR901483的完全立体控制的总合成，这将提供各种衍生物。
• Asymmetric Synthesis of Unsaturated Monocyclic and Bicyclic Nitrogen Heterocycles
  作者：Hiroshi Nomura、Christopher J. Richards

  DOI：10.1021/ol900880w

  日期：2009.7.2

  Hydrolysis of scalemic trichloroacetamides Cl3CCONHCH(R)CHCH2 and allylation, or acylation with but-3-enoic acid, followed by ring-closing metathesis resulted in the formation of unsaturated pyrrolidine and piperidine building blocks. These were employed in the synthesis of (S)-coniine (R = Pr) and a formal synthesis of (+)-anisomycin (R = p-MeOC5H4). Extension of this methodology with R = CH2CHCH2 employing two ring-closing metatheses resulted in the synthesis of unsaturated quinolizidinone and indolizidinone frameworks.
• STEREOCONTROLLED TOTAL SYNTHESIS OF (−)-FR901483
  作者：Toshiyuki Kan、Tohru Fukuyama、Shigeru Ieda、Akitaka Masuda、Toshiyuki Wakimoto、Mami Kariyama、Tomohiro Asakawa

  DOI：10.3987/com-12-s(n)38

  日期：——

  The total synthesis of a potent immunosuppressant (-)-FR901483 is accomplished. The skeleton itself is constructed by the Ugi 4CC reaction, subsequent intramolecular Dieckmann condensation, and a diastereoselective intramolecular aldol reaction. However, the remarkable feature is the stereoselective incorporation of the p-methoxybenzyl and methylamino groups within the tricyclic core skeleton.