2-((R)-1-Isopropyl-5-phenyl-pent-2-ynyl)-isoindole-1,3-dione | 850194-83-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2-((R)-1-Isopropyl-5-phenyl-pent-2-ynyl)-isoindole-1,3-dione
• 英文别名: 2-[(3R)-2-methyl-7-phenylhept-4-yn-3-yl]isoindole-1,3-dione
• CAS: 850194-83-1
• 化学式: C₂₂H₂₁NO₂
• 分子量: 331.414
• InChiKey: CHFDWFURCLDUDC-FQEVSTJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-((R)-1-Isopropyl-5-phenyl-pent-2-ynyl)-isoindole-1,3-dione 在 一水合肼 作用下， 以 乙醇 为溶剂， 以80%的产率得到(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
• 作为产物：
  描述：

  4-苯基-1-丁炔 在 N-甲基麻黄碱 、 zinc trifluoromethanesulfonate 、 三乙胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成 2-((R)-1-Isopropyl-5-phenyl-pent-2-ynyl)-isoindole-1,3-dione
  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