2-(but-3-en-1-yl)-2-phenylhex-5-en-1-amine | 1582779-59-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-(but-3-en-1-yl)-2-phenylhex-5-en-1-amine
• 英文别名: 2-homoallyl-2-phenyl-hex-5-enylamine
• CAS: 1582779-59-6
• 化学式: C₁₆H₂₃N
• 分子量: 229.365
• InChiKey: OCELNEACESMQAF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.82
• 重原子数：
  17.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  2-(but-3-en-1-yl)-2-phenylhex-5-en-1-amine 在 C₄₈H₆₆N₂O₂Zr^(2-) 、 三苯碳四(五氟苯基)硼酸盐 作用下， 以 氯苯 为溶剂， 反应 96.0h， 以99%的产率得到2,8-dimethyl-5-phenyl-1-azabicyclo[3.3.1]nonane
  参考文献：
  名称：

  带有桥联双（酚基）配体的锆配合物催化的分子内加氢胺化反应†

  摘要：

  合成和表征了由哌嗪啶和咪唑烷桥联的双（酚基）配体稳定的锆配合物。测试和比较了它们在催化分子内加氢反应中的活性，这揭示了辅助配体在影响催化活性中的重要作用。衍生自二苄基锆配合物的阳离子物种在催化伯胺和仲胺的分子内加氢胺化反应中均显示出良好的活性，并以85％至99％的产率提供了相应的N-杂环。此外，该催化体系还催化伯氨基二烯的顺序环化，并以94-99％的产率生成了双环叔胺。

  DOI：

  10.1039/c5ra23270h
• 作为产物：
  描述：

  2-(but-3-enyl)-2-phenylhex-5-enenitrile 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 以75.8%的产率得到2-(but-3-en-1-yl)-2-phenylhex-5-en-1-amine
  参考文献：
  名称：

  通过对映选择性加氢胺化锆催化的氨基二烯烃和氨基二炔的去对称化

  摘要：

  烯烃和胺的催化加成（加氢胺化）通常通过 CN 或 CH 键的形成直接提供 α- 或 β- 氨基立体中心。或者，对称氨基二烯烃或氨基二炔的去对称化反应提供了进入立体中心，其位置受底物结构控制的途径。在目前对映选择性锆催化加氢胺化的研究中，由 CN 键形成和前手性四元中心去对称化产生的立体中心由催化剂和反应条件独立控制。使用单一催化剂，该方法可以选择性地访问来自氨基二烯烃的光学富集的五元、六元和七元环胺的非对映异构体，以及五元、六元和七元环胺的对映选择性合成。和来自氨基二炔的七元环亚胺。氨基二烯烃加氢胺化实验测试了催化剂：底物比、催化剂的绝对浓度和伯胺底物的绝对初始浓度的影响，表明后一个参数强烈影响去对称化过程的立体选择性，而绝对构型CN 键形成产生的 α-氨基立体中心不受这些参数的影响。有趣的是，底物的同位素取代（H2NR 与 D2NR）增强了氨基二烯烃环化中对映选择性和非对映选择性过程的立

  DOI：

  10.1021/ja511250m

文献信息

• Highly enantioselective hydroamination to six-membered rings by heterobimetallic catalysts
  作者：Lenard Hussein、Nibadita Purkait、Mustafa Biyikal、Eugenia Tausch、Peter W. Roesky、Siegfried Blechert

  DOI：10.1039/c3cc48874h

  日期：——

  New bimetallic Zn/Zr salen-type systems were employed as catalysts in the asymmetric intramolecular hydroamination reaction. High enantioselectivity for the formation of piperidines of up to 98% ee were observed.

  新的双金属Zn/Zr salen型体系被用作不对称分子内氢氨化反应的催化剂。观察到高达98%对映体过量的哌啶生成的高对映选择性。
• β-SiH-Containing Tris(silazido) Rare-Earth Complexes as Homogeneous and Grafted Single-Site Catalyst Precursors for Hydroamination
  作者：Naresh Eedugurala、Zhuoran Wang、KaKing Yan、Kasuni C. Boteju、Umesh Chaudhary、Takeshi Kobayashi、Arkady Ellern、Igor I. Slowing、Marek Pruski、Aaron D. Sadow

  DOI：10.1021/acs.organomet.6b00956

  日期：2017.3.27

  A series of homoleptic rare-earth silazido compounds and their silica-grafted derivatives were prepared to compare spectroscopic and catalytic features under homogeneous and interfacial conditions. Trivalent tris(silazido) compounds LnN(SiHMe2)tBu}(3) (Ln = Sc (1), Y (2), Lu (3)) are prepared in high yield by salt metathesis reactions. Solution-phase and solid-state characterization of 1-3 by NMR and IR spectroscopy and X-ray diffraction reveals Ln-H-Si interactions. These features are retained in solvent coordinated 2 center dot Et2O, 2 center dot THF, and 3 center dot THF. The change in spectroscopic features characterizing the secondary interactions (v(s1H), (1)J(siH)) from the unactivated SiH in the silazane HN(SiHMe2)tBu follows the trend 3 > 2 > 1 approximate to 2 center dot THF approximate to 3 center dot THF. Ligand lability follows the same pattern, with Et2O readily dissociating from 2 center dot Et2O while THF is displaced only during surface grafting reactions. I and 2 center dot THF graft onto mesoporous silica nanoparticles (MSN) to give LnN(SiHMe2)tBu}(n)@MSN (Ln = Sc (1@MSN), Y (2@MSN)) along with THF and protonated silazido as HN(SiHMe2)tBu and H(2)NtBu. The surface species are characterized by multinuclear and multidimensional solid-state (SS) NMR spectroscopic techniques, as well as diffuse reflectance FTIR, elemental analysis, and reaction stoichiometry. A key (1)J(SiH) SSNMR measurement reveals that the grafted sites most closely resemble Ln.THF adducts, suggesting that siloxane coordination occurs in grafted compounds. These species catalyze the hydroamination/bicyclization of aminodialkenes, and both solution-phase and interfacial conditions provide the bicyclized product with equivalent cis:trans ratios. Similar diastereoselectivities mediated by catalytic sites under the two conditions suggest similar effective environments.