(S)-N-(non-4-yn-3-yl)-N-benzylamine | 850194-89-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-N-(non-4-yn-3-yl)-N-benzylamine
• 英文别名: (3S)-N-benzylnon-4-yn-3-amine
• CAS: 850194-89-7
• 化学式: C₁₆H₂₃N
• 分子量: 229.365
• InChiKey: IHAKQVPUNKERLX-INIZCTEOSA-N

物化性质

• 沸点：
  329.0±25.0 °C(Predicted)
• 密度：
  0.929±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (S)-N-(non-4-yn-3-yl)-N-benzylamine 、 一氧化碳 在 palladium dichloride 对苯醌 、 copper dichloride 作用下， 以 四氢呋喃 为溶剂， 40.0 ℃ 、2.07 MPa 条件下， 反应 12.0h， 生成 (S)-(-)-(E)-α-(1-chloropentylidene)-β-ethyl-N-benzyl-β-lactam 、 (R)-(+)-(E)-α-(1-chloropentylidene)-β-ethyl-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：

  (R)-4-nonyn-3-yl acetate 在 氢氧化钾 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 生成 (S)-N-(non-4-yn-3-yl)-N-benzylamine
  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

• PdCl₂-Catalyzed Efficient Transformation of Propargylic Amines to (<i>E</i>)-α-Chloroalkylidene-β-lactams
  作者：Shengming Ma、Bin Wu、Xuefeng Jiang

  DOI：10.1021/jo0480996

  日期：2005.4.1

  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.