(R)-N-(2-methyl-7-phenylhept-4-yn-3-yl)amine | 850194-87-5

• 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: (R)-N-(2-methyl-7-phenylhept-4-yn-3-yl)amine
• 英文别名: (3R)-2-methyl-7-phenylhept-4-yn-3-amine
• CAS: 850194-87-5
• 化学式: C₁₄H₁₉N
• 分子量: 201.312
• InChiKey: WODBPTOXFLBMRM-AWEZNQCLSA-N

物化性质

• 沸点：
  314.7±35.0 °C(Predicted)
• 密度：
  0.963±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  (R)-N-(2-methyl-7-phenylhept-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 16.0h， 生成 (R)-(+)-(E)-α-(1-chloro-3-phenylpropylidene)-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：

  (3S)-3-hydroxy-2-methyl-7-phenyl-4-heptyne 在 一水合肼 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 (R)-N-(2-methyl-7-phenylhept-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