(Z)-5-(4-Methoxyphenyl)-4-penten-1-amine | 155768-36-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (Z)-5-(4-Methoxyphenyl)-4-penten-1-amine
• 英文别名: (Z)-5-(4-methoxyphenyl)pent-4-en-1-amine
• CAS: 155768-36-8
• 化学式: C₁₂H₁₇NO
• 分子量: 191.273
• InChiKey: VMAPLZSFZYIAJL-HYXAFXHYSA-N

物化性质

• 沸点：
  329.8±30.0 °C(predicted)
• 密度：
  1.000±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  (Z)-5-(4-Methoxyphenyl)-4-penten-1-amine 在 六甲基二硅氧烷 、 phosphorus pentoxide 、 三乙胺 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 1.5h， 生成 5-[1-(4-Methoxy-phenyl)-meth-(E)-ylidene]-6-methyl-2,3,4,5-tetrahydro-pyridine
  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-(4-Methoxy-phenyl)-pent-4-enenitrile 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 1.75h， 生成 (Z)-5-(4-Methoxyphenyl)-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

• Palladium-Catalyzed Regioselective C–H Iodination of Unactivated Alkenes
  作者：Benedikt S. Schreib、Erick M. Carreira

  DOI：10.1021/jacs.9b03998

  日期：2019.6.5

  A palladium-catalyzed C-H iodination of unactivated alkenes is reported. A picolinamide directing group enables the regioselective functionalization of a wide array of olefins to furnish iodination products as single stereoisomers. Mechanistic investigations suggest the reversible formation of a six-membered alkenyl palladacycle intermediate through a turnover-limiting C-H activation.

  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。
• Synthesis of Chiral Hydroxylated Quinolizidines via Vinylogous Bischler-Napieralski Nitrilium Ion Cyclizations
  作者：Angela L. Marquart、Brent L. Podlogar、Edward W. Huber、David A. Demeter、Norton P. Peet、Herschel J. R. Weintraub、Michael R. Angelastro

  DOI：10.1021/jo00087a026

  日期：1994.4

  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.
• Photoinduced Disulfide-Catalyzed Intramolecular Anti-Markovnikov Hydroamination through <i>in Situ</i> N–S Species
  作者：Guoxiang Zhang、Hui He、Xiaoxiao Chen、Shao-Fei Ni、Rong Zeng

  DOI：10.1021/acs.orglett.3c00508

  日期：2023.3.10

  6-triisopropylphenyl) disulfide, an inexpensive reagent with relatively low oxidative ability, as a photo and hydrogen atom transfer catalyst to achieve intramolecular hydroamination. The mechanistic studies as well as the DFT calculations are consistent with a novel process involving N-centered radical generation through the homolysis of the in situ formed N–S species and subsequent cyclization. An

  烯烃的光诱导反马尔可夫尼科夫加氢胺化通常需要具有高氧化能力的光催化剂来引发单电子过程。在此，我们交替使用双（2,4,6-三异丙基苯基）二硫化物，一种氧化能力相对较低的廉价试剂，作为光和氢原子转移催化剂来实现分子内加氢胺化。机理研究以及 DFT 计算与涉及通过原位形成的 N-S 物种均裂和随后的环化产生 N 中心自由基的新过程一致。可以获得一系列不同的含氮循环。