N-(2-methylnon-4-yn-3-yl)amine | 850194-78-4

• 分子结构分类: 有机化合物 - 有机磷化合物
• 英文名称: N-(2-methylnon-4-yn-3-yl)amine
• 英文别名: 2-Methylnon-4-yn-3-amine
• CAS: 850194-78-4
• 化学式: C₁₀H₁₉N
• 分子量: 153.268
• InChiKey: CYMNVXYXYMXMSZ-UHFFFAOYSA-N

物化性质

• 沸点：
  215.3±23.0 °C(Predicted)
• 密度：
  0.845±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  N-(2-methylnon-4-yn-3-yl)amine 在 palladium dichloride potassium carbonate 、 对苯醌 、 copper dichloride 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 20.0~40.0 ℃ 、2.07 MPa 条件下， 反应 12.0h， 生成 (E)-α-(1-chloropentylidene)-β-(isopropyl)-N-benzyl-β-lactam
  参考文献：
  名称：

  PdCl₂-Catalyzed Efficient Transformation of Propargylic Amines to (E)-α-Chloroalkylidene-β-lactams

  摘要：

  The PdCl2-catalyzed cyclocarbonylation reaction of propargylic amines with CuCl2 and benzoquinone afforded (E)-alpha-chloroalkylidene-beta-lactams in moderate to good yields. The formation of the corresponding Z-isomers or five-membered products was not observed. The reaction of the readily available optically active propargylic amines provides a convenient synthesis of the corresponding (E)-alpha-chloroalkylidene-beta-lactams with high ee values. The structure and the stereochemistry of the products were established by the X-ray single-crystal diffraction study of (E)-6d and (E)-6e, which indicates that the stereoselectivity in this reaction is different from what was observed with propargylic alcohols. A rationale for this reaction was proposed.

  DOI：

  10.1021/jo0480996
• 作为产物：
  描述：

  2-(1-Isopropyl-hept-2-ynyl)-isoindole-1,3-dione 在 一水合肼 作用下， 以 乙醇 为溶剂， 以53%的产率得到N-(2-methylnon-4-yn-3-yl)amine
  参考文献：
  名称：

  PdCl₂-Catalyzed Efficient Transformation of Propargylic Amines to (E)-α-Chloroalkylidene-β-lactams

  摘要：

  The PdCl2-catalyzed cyclocarbonylation reaction of propargylic amines with CuCl2 and benzoquinone afforded (E)-alpha-chloroalkylidene-beta-lactams in moderate to good yields. The formation of the corresponding Z-isomers or five-membered products was not observed. The reaction of the readily available optically active propargylic amines provides a convenient synthesis of the corresponding (E)-alpha-chloroalkylidene-beta-lactams with high ee values. The structure and the stereochemistry of the products were established by the X-ray single-crystal diffraction study of (E)-6d and (E)-6e, which indicates that the stereoselectivity in this reaction is different from what was observed with propargylic alcohols. A rationale for this reaction was proposed.

  DOI：

  10.1021/jo0480996

文献信息

• Regio- and Stereoselective Synthesis of Fluoroalkenes by Directed Au(I) Catalysis
  作者：Benjamin C. Gorske、Curren T. Mbofana、Scott J. Miller

  DOI：10.1021/ol9016782

  日期：2009.10.1

  Au-catalyzed hydrofluorination reactions of a range of functionalized alkynes are reported. In the presence of an appropriate directing group, localized with particular spacing from the pendant alkyne, regioselective and predictable conversion of the alkyne to the Z-vinyl fluoride may be achieved, In selected cases, yields and selectivities are excellent. Additional experiments with two directing groups installed have established some initial principles with respect to a hierarchy of directing groups and their capacity for influencing hydrofluorination regioselectivity.