1-Methyl-octa-5,6-dienylamine | 96838-85-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1-Methyl-octa-5,6-dienylamine
• CAS: 96838-85-6
• 化学式: C₉H₁₇N
• 分子量: 139.241
• InChiKey: DRIISOLDLIGSJC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  1-Methyl-octa-5,6-dienylamine 在 (pentamethylcyclopentadienyl)2SmCH(TMS)2 作用下， 生成 (2S,6S)-2-Methyl-6-((E)-propenyl)-piperidine
  参考文献：
  名称：

  Organolanthanide-Catalyzed Intramolecular Hydroamination/Cyclization of Aminoallenes

  摘要：

  DOI：

  10.1021/ja9743248
• 作为产物：
  描述：

  2-Hepta-4,5-dienyl-2-methyl-[1,3]dioxolane 在 sodium carbonate lithium aluminium tetrahydride 、 三氯化铝 、 盐酸羟胺 、 4-甲基苯磺酸吡啶 作用下， 以 甲醇 、 乙醚 、 水 为溶剂， 生成 1-Methyl-octa-5,6-dienylamine
  参考文献：
  名称：

  An efficient synthesis of (±)-pinidine

  摘要：

  DOI：

  10.1016/s0040-4039(00)89121-2

文献信息

• 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.