(Z)-5-Phenyl-4-penten-1-amine | 35840-83-6

• 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: (Z)-5-Phenyl-4-penten-1-amine
• 英文别名: (Z)-5-phenylpent-4-en-1-amine；(Z)-5-phenyl-4-pentenylamine；(Z)-5-phenylpent-4-enylamine
• CAS: 35840-83-6
• 化学式: C₁₁H₁₅N
• 分子量: 161.247
• InChiKey: PNXDDJPALLQFMY-UITAMQMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.44
• 重原子数：
  12.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  26.02
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (Z)-5-Phenyl-4-penten-1-amine 在 N,N-二异丙基乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 10.0h， 生成 (Z)-Ethyl 5-<(5-phenyl-4-pentenyl)amino>-5-oxopentanoate
  参考文献：
  名称：

  Synthesis of Chiral Hydroxylated Quinolizidines via Vinylogous Bischler-Napieralski Nitrilium Ion Cyclizations

  摘要：

  Treatment of the amido esters 9 and 17 with PPSE (polyphosphoric acid trimethylsilyl ester) followed by NaBH4 in ethanol gave the quinolizidinones 11-14 and 19 via a vinylogous Bischler-Napieralski nitrilium ion cyclization-reductive lactamization two-step process. Subsequent ozonolysis and reduction afforded chiral hydroxylated quinolizidines in moderate to good yield. In contrast to five-membered-ring formation, six-membered-ring formation via nitrilium-ion cyclization requires a p-methoxy-substituted styryl terminator. The effect para-substituted styryl terminators have on the energy of activation and Delta H for the cyclization process has been calculated by semiempirical and ab initio methods.

  DOI：

  10.1021/jo00087a026
• 作为产物：
  描述：

  (Z)-5-phenylpent-4-enenitrile 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 1.75h， 以92%的产率得到(Z)-5-Phenyl-4-penten-1-amine
  参考文献：
  名称：

  未活化烯烃的钯催化区域选择性 C-H 碘化

  摘要：

  报道了钯催化的未活化烯烃的 CH 碘化。吡啶酰胺导向基团能够对多种烯烃进行区域选择性官能化，以提供单一立体异构体形式的碘化产物。机理研究表明，六元烯基钯环中间体通过限制营业额的 CH 活化可逆形成。

  DOI：

  10.1021/jacs.9b03998

文献信息

• Stereospecific synthesis of Z olefins bearing an ω-azido group
  作者：A. Chhen、M. Vaultier、R. Carrié

  DOI：10.1016/s0040-4039(01)80552-9

  日期：1989.1

  Ylides derived from ω-azidoalkyltriphenylphosphonium salts were generated at low temperature. They are stable at −80°C for several hours and react smoothly and stereospecifically with typical aldehydes to form Z-ω-azido olefins which are the precursors of ω-unsaturated primary and secondary amines.

  ω-叠氮基烷基三苯基phosph盐衍生的叶立德在低温下生成。它们在-80°C稳定数小时，并且与典型的醛平稳且立体定向反应，形成Z-ω-叠氮基烯烃，它们是ω-不饱和伯胺和仲胺的前体。
• Catalytic Arylalkylation of Alkenyl Amines at Remote Sites via Directed Nickel Catalysis
  作者：Jian Han、Yinheng Tang、Jie Huang、Chun Luo、Lanlan Zhang、Wenyi Li、Chao Wang

  DOI：10.1002/cjoc.202200647

  日期：2023.3.15

  due to the preference for formation of kinetically stable five-membered metallacycles. Herein, we have disclosed a complementary strategy to accomplish a nickel-catalyzed remote arylalkylation of alkenyl amines with excellent regioselectivity and diastereofidelity, involving rare six- or seven-membered metallacycles. This general protocol is compatible with a series of δ- and ε-alkenyl amines, providing

  指导基团辅助、过渡金属催化的烯烃三组分双官能化已成为推动分子复杂性的有力工具。然而，由于倾向于形成动力学稳定的五元金属环，这种策略通常适用于带有靠近烯烃部分的定向基团的底物。在此，我们公开了一种互补策略，以实现具有优异区域选择性和非对映保真度的烯基胺的镍催化远程芳基烷基化，涉及稀有的六元或七元金属环。此通用协议与一系列δ - 和ε -烯基胺兼容，提供相应有价值的δ、ε - 和ε, ζ -难以合成的双官能化脂肪胺。双齿吡啶酰胺助剂的配位和烷基卤化物对 Ni(I) 物种的轻松氧化加成是所开发的远程烯烃双碳官能化成功的关键。
• Lovick, Helena M.; Michael, Forrest E., Journal of the American Chemical Society, 2010, vol. 132, p. 1249 - 1251
  作者：Lovick, Helena M.、Michael, Forrest E.

  DOI：——

  日期：——
• Brønsted Acid-Catalyzed Intramolecular Hydroamination of Protected Alkenylamines. Synthesis of Pyrrolidines and Piperidines
  作者：Björn Schlummer、John F. Hartwig

  DOI：10.1021/ol025659j

  日期：2002.5.1

  [GRAPHIC]The cyclization of aminoalkenes bearing an electron-withdrawing group on the nitrogen atom was catalyzed by triflic or sulfuric acid in toluene. Pyrrolidines and piperidines were formed in excellent yields. N-Phenylanilides also underwent cyclization to form gamma-lactams.
• Convenient Route to Primary (<i>Z</i>)-Allyl Amines and Homologs
  作者：Alejandra Gerpe、Mariela Bollini、Mercedes González、Hugo Cerecetto

  DOI：10.1080/00397910802369596

  日期：2008.12.16

  A convenient two-step procedure for the synthesis of primary (Z)-allyl amines, (Z)-homoallyl amines [(Z)-but-3-enylamines], and (Z)-pent-4-enylamines using the Wittig reaction was achieved. The use of nonstabilized ylides from triphenylphosphonium salt, potassium salt, and apolar solvent produced (Z/E)geometric isomer ratios generally greater than 1.6. The amine moiety was masked using a phtalimide group that was removed successfully in the last step of the process in two different conditions, NH2NH2/EtOH/rt or CH3NH2/EtOH/rt. However, in some cases, reduction of the C=C double bond in the deprotection with hydrazine was concomitantly observed.