5,6-octadienylamine | 161009-85-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 5,6-octadienylamine
• CAS: 161009-85-4
• 化学式: C₈H₁₅N
• 分子量: 125.214
• InChiKey: FGPHEYLBFNJEGA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5,6-octadienylamine 在 [Me2Si(η5-Me4C5)(t-BuN)]U(NMe2)2 作用下， 以 氘代苯 为溶剂， 生成 2-[(1Z)-1-丙烯-1-基]哌啶
  参考文献：
  名称：

  Constrained Geometry Organoactinides as Versatile Catalysts for the Intramolecular Hydroamination/Cyclization of Primary and Secondary Amines Having Diverse Tethered C−C Unsaturation

  摘要：

  A series of "constrained geometry" organoactinide complexes, (CGC)An(NMe)(2) (CGC = Me2Si(eta(5)-Me4C5)((BuN)-Bu-t); An = Th, 1; U, 2), has been prepared via efficient in situ, two-step protodeamination routes in good yields and high purity. Both 1 and 2 are quantitatively converted to the neutrally charged, solvent-free dichlorides (1-Cl-2, 2-Cl-2) and slightly more soluble diiodides (1-I-2, 2-I-2) with excess Me3Si-X (X = Cl, I) in non-coordinating solvents. The new complexes were characterized by NMR spectroscopy, elemental analysis, and (for 1 and 2) single-crystal X-ray diffraction, revealing substantially increased metal coordinative unsaturation vs the corresponding Me2SiCp ''(2)AnR(2) (Cp '' = eta(5)-Me4C5; An = Th, R = CH2(SiMe3), 3; An = U, R = CH2Ph, 4) and Cp'(2)AnR(2) (Cp' = eta(5)-Me5C5 ; An = Th, R = CH2(SiMe3), 5; An = U, R = CH2(SiMe3), 6) complexes. Complexes 1-6 exhibit broad applicability for the intramolecular hydroamination of diverse C-C unsaturations, including terminal and internal aminoalkenes (primary and secondary amines), aminoalkynes (primary and secondary amines), aminoallenes, and aminodienes. Large turnover frequencies (N-t up to 3000 h(-1)) and high regioselectivities (>= 95%) are observed throughout, along with moderate to high diastereoselectivities (up to 90% trans ring closures). With several noteworthy exceptions, reactivity trends track relative 5f ionic radii and ancillary ligand coordinative unsaturation. Reactivity patterns and activation parameters are consistent with a reaction pathway proceeding via turnover-limiting CC/CC insertion into the An-N sigma-bond.

  DOI：

  10.1021/ja0665444
• 作为产物：
  描述：

  hexa-3,4-diene-1-ol 在 吡啶 、 lithium aluminium tetrahydride 、 正丁基锂 、 sodium iodide 作用下， 以 乙醚 、 丙酮 为溶剂， 反应 76.0h， 生成 5,6-octadienylamine
  参考文献：
  名称：

  Davies, Ian W.; Shaw, Robert W.; Wisedale, Richard, Journal of the Chemical Society. Perkin transactions I, 1994, # 24, p. 3557 - 3562

  摘要：

  DOI：

文献信息

• Highly Active Au(I) Catalyst for the Intramolecular <i>e</i><i>xo</i>-Hydrofunctionalization of Allenes with Carbon, Nitrogen, and Oxygen Nucleophiles
  作者：Zhibin Zhang、Cong Liu、Robert E. Kinder、Xiaoqing Han、Hua Qian、Ross A. Widenhoefer

  DOI：10.1021/ja062045r

  日期：2006.7.19

  Au-catalyzed intramolecular hydroalkoxylation within minutes at room temperature to form the corresponding oxygen heterocycles in good yield with high exo-selectivity. 2-Allenyl indoles underwent Au-catalyzed intramolecular hydroarylation within minutes at room temperature to form 4-vinyl tetrahydrocarbazoles in good yield. Au-catalyzed cyclization of N-allenyl carbamates, allenyl alcohols, and 2-allenyl

  (2,2-二苯基-4,5-己二烯基)氨基甲酸苄酯 (4) 与 Au[P(t-Bu)2(o-biphenyl)]Cl (2) 和 AgOTf 的 1:1 催化混合物反应5 mol%) 在二恶烷中在 25 摄氏度下 45 分钟导致 4,4-二苯基-2-乙烯基吡咯烷-1-羧酸苄酯 (5) 的分离，产率为 95%。Au(I) 催化的 N-烯丙氨基甲酸酯的分子内加氢胺化耐受烷基和烯基碳原子处的取代，并且对于哌啶衍生物的形成是有效的。γ-羟基和δ-羟基丙二烯也在室温下几分钟内经历了金催化的分子内加氢烷氧基化，以高产率和高外选择性形成相应的氧杂环。2-烯基吲哚在室温下几分钟内经历金催化的分子内加氢芳基化，以良好的产率形成4-乙烯基四氢咔唑。
• Organolanthanide-Catalyzed Intramolecular Hydroamination/Cyclization of Aminoallenes
  作者：Victor M. Arredondo、Frank E. McDonald、Tobin J. Marks

  DOI：10.1021/ja9743248

  日期：1998.5.1
• Constrained Geometry Organoactinides as Versatile Catalysts for the Intramolecular Hydroamination/Cyclization of Primary and Secondary Amines Having Diverse Tethered C−C Unsaturation
  作者：Bryan D. Stubbert、Tobin J. Marks

  DOI：10.1021/ja0665444

  日期：2007.4.1

  A series of "constrained geometry" organoactinide complexes, (CGC)An(NMe)(2) (CGC = Me2Si(eta(5)-Me4C5)((BuN)-Bu-t); An = Th, 1; U, 2), has been prepared via efficient in situ, two-step protodeamination routes in good yields and high purity. Both 1 and 2 are quantitatively converted to the neutrally charged, solvent-free dichlorides (1-Cl-2, 2-Cl-2) and slightly more soluble diiodides (1-I-2, 2-I-2) with excess Me3Si-X (X = Cl, I) in non-coordinating solvents. The new complexes were characterized by NMR spectroscopy, elemental analysis, and (for 1 and 2) single-crystal X-ray diffraction, revealing substantially increased metal coordinative unsaturation vs the corresponding Me2SiCp ''(2)AnR(2) (Cp '' = eta(5)-Me4C5; An = Th, R = CH2(SiMe3), 3; An = U, R = CH2Ph, 4) and Cp'(2)AnR(2) (Cp' = eta(5)-Me5C5 ; An = Th, R = CH2(SiMe3), 5; An = U, R = CH2(SiMe3), 6) complexes. Complexes 1-6 exhibit broad applicability for the intramolecular hydroamination of diverse C-C unsaturations, including terminal and internal aminoalkenes (primary and secondary amines), aminoalkynes (primary and secondary amines), aminoallenes, and aminodienes. Large turnover frequencies (N-t up to 3000 h(-1)) and high regioselectivities (>= 95%) are observed throughout, along with moderate to high diastereoselectivities (up to 90% trans ring closures). With several noteworthy exceptions, reactivity trends track relative 5f ionic radii and ancillary ligand coordinative unsaturation. Reactivity patterns and activation parameters are consistent with a reaction pathway proceeding via turnover-limiting CC/CC insertion into the An-N sigma-bond.
• Davies, Ian W.; Shaw, Robert W.; Wisedale, Richard, Journal of the Chemical Society. Perkin transactions I, 1994, # 24, p. 3557 - 3562
  作者：Davies, Ian W.、Shaw, Robert W.、Wisedale, Richard、Gallagher, Timothy

  DOI：——

  日期：——