N-(3,7-dimethyl-2Z,6E-octadienyl)morpholine | 46742-25-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: N-(3,7-dimethyl-2Z,6E-octadienyl)morpholine
• 英文别名: (Z)-4-(3,7-dimethylocta-2,6-dienyl)morpholine；4-(3,7-dimethyl-octa-2,6-dienyl)-morpholine；4-[(2Z)-3,7-dimethylocta-2,6-dienyl]morpholine
• CAS: 46742-25-0
• 化学式: C₁₄H₂₅NO
• 分子量: 223.359
• InChiKey: YUTWIQSOWDYOKV-AUWJEWJLSA-N

物化性质

• 沸点：
  313.9±30.0 °C(Predicted)
• 密度：
  0.911±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  ((Z)-3,7-Dimethyl-octa-2,6-dienyl)-diethyl-methyl-ammonium; iodide 、 monomagnesium monomorpholin-4-ide 在 bis(acetylacetonato)palladium(II) 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以52%的产率得到N-(3,7-dimethyl-2Z,6E-octadienyl)morpholine
  参考文献：
  名称：

  Novel palladium complex-catalyzed reaction of magnesium amides with allylic electrophiles

  摘要：

  DOI：

  10.1007/bf00959383

文献信息

• Hydrogen-Bond-Assisted Activation of Allylic Alcohols for Palladium-Catalyzed Coupling Reactions
  作者：Yasemin Gumrukcu、Bas de Bruin、Joost N. H. Reek

  DOI：10.1002/cssc.201300723

  日期：2014.3

  We report direct activation of allylic alcohols using a hydrogen‐bond‐assisted palladium catalyst and use this for alkylation and amination reactions. The novel catalyst comprises a palladium complex based on a functionalized monodentate phosphoramidite ligand in combination with urea additives and affords linear alkylated and aminated allylic products selectively. Detailed kinetic analysis show that

  我们报道了使用氢键辅助钯催化剂直接活化烯丙醇，并将其用于烷基化和胺化反应。该新型催化剂包含基于官能化的单齿亚磷酰胺配体的钯配合物与脲添加剂的组合，并选择性地提供线性烷基化和胺化的烯丙基产物。详细的动力学分析表明，烯丙醇的氧化加成是决定速率的步骤，醇，配体官能团和其他尿素添加剂之间的氢键促进了烯丙基醇的氧化。
• Syntheses of Isoprenoids by Telomerizations. IX. Stereoselectivity of Telomers and the Effect of Telogens in Anionic Telomerizations Using Secondary Amines
  作者：Kunihiko Takabe、Takao Katagiri、Juntaro Tanaka

  DOI：10.1246/bcsj.46.222

  日期：1973.1

  The stereoselectivity of the telomers and the effect of the telogens in the anionic telomerizations of isoprene with secondary amines were investigated. Dimethyl-, diethyl-, di-n-propy-1, diisopropyl-, and methylphenyl-amines, pyrrolidine, morpholine, and piperidine were used as the telogens. The ratio of N,N-dialkyl(3,7-dimethyl-2,6-octadienyl)amine(2A) to N,N-dialkyl(2-isopropenyl-5-methyl-4-hexenyl)amine(2B), which were obtained in these reactions, was varied with the sort of secondary amines, the yield of the telomers was found to be dependent on the acidity of the secondary amines. Moreover, 2A, which was the main component of the n=2 telomers, was confirmed to have a cis-configuration—that is, N,N-dialkylnerylamine. However, the n=1 telomer of myrcene with secondary amine was N,N-dialkylgeranylamine. These results were interpreted in terms of the stability of the cyclic intermediate of the carbanions.

  研究了异戊二烯与二级胺进行阴离子延长聚合反应中的延长剂的立体选择性及其影响。使用了二甲基、二乙基、正丙基、异丙基和甲基苯胺、吡咯烷、哌啶和吗啉作为延长剂。反应中获得的N,N-二烷基（3,7-二甲基-2,6-辛二烯基）胺（2A）与N,N-二烷基（2-异丙烯基-5-甲基-4-己烯基）胺（2B）的比例随着二级胺的种类变化，且延长聚合物的产率与二级胺的酸性相关。此外，确认n=2延长聚合物的主要成分2A具有顺式构型，即N,N-二烷基尼烯胺。然而，与二级胺反应的美克烯的n=1延长聚合物为N,N-二烷基杰拉尼胺。这些结果可以通过羰基阴离子环状中间体的稳定性进行解释。
• Novel Palladium‐Catalysed Hydroamination of Myrcene and Catalyst Separation by Thermomorphic Solvent Systems
  作者：Arno Behr、Leif Johnen、Nils Rentmeister

  DOI：10.1002/adsc.201000283

  日期：2010.10.9

  the hydroamination of myrcene with morpholine is catalysed by palladium complexes with bidentate ligands such as bis(diphenylphosphino)butane (DPPB) or bis(2-diphenylphosphinophenyl) ether (DPEphos). The systematic optimisation of the reaction parameters under single-phase conditions led to yields of the 1,4-adducts of higher than 90%. The only side products proved to be the telomers of myrcene, whose

  加氢胺化是一种优雅且原子经济的反应，可将烯烃转化为胺。该反应的少数技术上的实现之一是月桂烯加氢氨基化为二乙基香叶胺，后者是（-）-薄荷醇的重要前体。但是，这种所谓的“高砂工艺”是由大量的碱金属（尤其是锂）催化的，这使其成为一种相对昂贵的方法。在目前的工作中，月桂烯与吗啉的加氢催化反应是通过钯配合物与二齿配体如双（二苯基膦基）丁烷（DPPB）或双（2-二苯基膦基苯基）醚（DPEphos）进行的。在单相条件下系统优化反应参数可导致1,90加合物的收率高于90％。唯一的副产品被证明是月桂烯的端粒，通过使用适当的反应条件可以减少其形成。成功地应用了与温度有关的溶剂系统的方法，以使钯浸出率低于1.0％，从而从胺中分离出钯催化剂。
• Novel palladium complex-catalyzed reaction of magnesium amides with allylic electrophiles
  作者：U. M. Dzhemilev、A. G. Ibragimov、D. L. Minsker、R. R. Muslukhov

  DOI：10.1007/bf00959383

  日期：1987.2