(E)-N-<2-methyl-1-methylene-4-<(trimethylsilyl)oxy>-2-butenyl>morpholine | 124803-50-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: (E)-N-<2-methyl-1-methylene-4-<(trimethylsilyl)oxy>-2-butenyl>morpholine
• 英文别名: trimethyl-[(2E)-3-methyl-4-morpholin-4-ylpenta-2,4-dienoxy]silane
• CAS: 124803-50-5
• 化学式: C₁₃H₂₅NO₂Si
• 分子量: 255.432
• InChiKey: ISIOLKZKOOWUPQ-WUXMJOGZSA-N

物化性质

• 沸点：
  341.1±42.0 °C(Predicted)
• 密度：
  0.950±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.63
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-N-<2-methyl-1-methylene-4-<(trimethylsilyl)oxy>-2-butenyl>morpholine 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 生成
  参考文献：
  名称：

  通过非对映选择性的aza-Diels-Alder反应获得5,8-二取代的吲哚唑烷和1,4-二取代的喹唑烷环核的简洁且收敛的途径。

  摘要：

  [反应：见正文]描述了5,8-二取代的吲哚并立定和1,4-喹啉并立骨架的短而收敛的合成。合成途径的关键步骤是2-氨基二烯与N-烯丙基或N-高烯丙基亚胺的aza-Diels-Alder反应和闭环复分解反应。双环生物碱类似物以总非对映选择性并通过共同途径获得。

  DOI：

  10.1021/ol0260021
• 作为产物：
  描述：

  3-甲基-2-戊烯-4-炔醇 在 mercury(II) diacetate 、 三乙胺 、 六甲基二硅氮烷 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 9.0h， 生成 (E)-N-<2-methyl-1-methylene-4-<(trimethylsilyl)oxy>-2-butenyl>morpholine
  参考文献：
  名称：

  Catalytic aminomercuration reactions of 3-alken-1-ynes: an improved method for the synthesis of 2-amino-1,3-butadienes and 1-aza-1,3-butadienes

  摘要：

  Catalytic aminomercuration of 3-alken-1-ynes leads to 1-aza-1,3-butadienes and 2-amino-1,3-butadienes. Under appropriate reaction conditions it is possible to prepare these compounds via mercuration of 3-alken-1-ynes in the presence of either aromatic or aliphatic primary and secondary amines. Depending on the substituents in the starting 3-alken-1-yne, the mercuration reaction may afford gamma-amino enamines instead of 2-amino-1,3-butadienes and 3-imino amines or 4-amino-1-aza-1,3-butadienes instead of 1-aza-1,3-butadienes.

  DOI：

  10.1021/jo00021a039

文献信息

• Reactivity of 2-morpholinobutadienes with heterocumulenes: Stereoselective synthesis of thiins and new 2-morpholinobutadiene derivatives
  作者：José Barluenga、Fernando Aznar、Carlos Valdés、Fernando López Ortiz

  DOI：10.1016/s0040-4039(00)97853-5

  日期：1990.1

  2-Morpholinobutadienes have been found to show different behaviour in the reaction with isocyanates and isothiocyanates. While isocyanates give rise always to open chain compounds, isothiocyanates yield mainly thiin1 derivatives.

  已经发现2-甲硫基丁二烯在与异氰酸酯和异硫氰酸酯的反应中显示出不同的行为。尽管异氰酸酯总是产生开链化合物，但异硫氰酸酯主要产生噻吩1衍生物。
• Reactions of 2‐Amino‐1,3‐butadienes and Fischer Alkynyl Carbenes: Up to Nine C−C Bonds and Seven Stereogenic Centers Created in a Stereoselective Manner through a Cascade Process
  作者：José Barluenga、Fernando Aznar、Sofía Barluenga、Mónica Fernández、Alfredo Martín、Santiago García‐Granda、Alejandro Piñera‐Nicolás

  DOI：10.1002/(sici)1521-3765(19981102)4:11<2280::aid-chem2280>3.0.co;2-#

  日期：1998.11.2
• Stereoselective synthesis of 4-piperidone and 4-aminotetrahydropyridine derivatives by the imino Diels-Alder reaction of 2-amino-1,3-butadienes
  作者：Jose Barluenga、Fernando Aznar、Carlos Valdes、Maria Paz Cabal

  DOI：10.1021/jo00064a030

  日期：1993.6

  2-Amino-4-(alkoxymethyl)-1,3-butadienes react smoothly with nonactivated aldimines derived from aromatic aldehydes in the presence of ZnCl2 as Lewis acid giving rise, with good yields and very high stereoselectivity, to substituted 4-aminotetrahydropyridines which upon hydrolysis yield 4-piperidone derivatives. Moreover, the stereochemistry of the cyclization process depends on the nature of the N-substituent of the imine.
• Solid-Phase Synthesis of Polysubstituted Piperidines by Imino-Diels−Alder Cycloaddition of 2-Amino-1,3-butadienes with Solid-Supported Imines
  作者：José Barluenga、Carlos Mateos、Fernando Aznar、Carlos Valdés

  DOI：10.1021/ol026614l

  日期：2002.10.1

  [GRAPHICS]The solid-phase imino-Diels-Alder reaction of 2-amino-1,3-butadienes with solid-supported imines is described. The reaction furnishes 4-piperidones and 4-aminopiperidines with high diastereoselectivity and with very good yields and purity after the release from the solid support. The possibility of introducing variations in both cycloaddition partners gives rise to substituted piperidines with up to five elements of diversity.
• 2-Morpholinobutadienes as synthon for the regioselective preparation of 3-Morpholino-1,4-pentadienes and β-hydroxyvinylketones
  作者：José Barluenga、Fernando Aznar、Ma Paz Cabal、Carlos Valdés

  DOI：10.1016/s0040-4039(01)93506-3

  日期：1989.1