(E)-4-(1-chloromethylidene)-2-phenyl-3-oxa-1-aza-spiro[4.5]dec-1-ene | 1033037-48-7

• 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: (E)-4-(1-chloromethylidene)-2-phenyl-3-oxa-1-aza-spiro[4.5]dec-1-ene
• 英文别名: (E)-4-(chloromethylidene)-3-oxa-2-phenyl-1-azaspiro[4,5]dec-1-ene；(4E)-4-(chloromethylidene)-2-phenyl-3-oxa-1-azaspiro[4.5]dec-1-ene
• CAS: 1033037-48-7
• 化学式: C₁₅H₁₆ClNO
• 分子量: 261.751
• InChiKey: DDXXNNGGLFHPRL-ACCUITESSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-(1-ethynylcyclohexyl)benzamide 在 N-氯代丁二酰亚胺 、 copper dichloride 作用下， 以 乙腈 为溶剂， 以32%的产率得到(E)-4-(1-chloromethylidene)-2-phenyl-3-oxa-1-aza-spiro[4.5]dec-1-ene
  参考文献：
  名称：

  Copper(II)-Catalyzed Alkoxyhalogenation of Alkynyl Ureas and Amides as a Route to Haloalkylidene-Substituted Heterocycles

  摘要：

  A highly effective synthesis of haloalkylidene-substituted heterocycles by copper(II)-catalyzed cyclization of alkynyl ureas and secondary amides has been developed. The reaction, which involves a catalytic amount of CuCl2 and a stoichiometric amount of N-halosuccinimide, occurs selectively through an alkoxyhalogenation process. Alternatively, alkoxychlorination and alkoxybromination reactions can be performed working solely with stoichiometric CuCl, and CuBr2, respectively.

  DOI：

  10.1021/acs.joc.5b01227

文献信息

• Intramolecular Pd(II)-Catalyzed Cyclization of Propargylamides: Straightforward Synthesis of 5-Oxazolecarbaldehydes
  作者：Egle M. Beccalli、Elena Borsini、Gianluigi Broggini、Giovanni Palmisano、Silvia Sottocornola

  DOI：10.1021/jo800621n

  日期：2008.6.1

  Direct synthesis of 2-substituted 5-oxazolecarbaldehydes was performed by intramolecular reaction of propargylamides through treatment with a catalytic amount of Pd(II) salts in the presence of a stoichiometric amount of reoxidant agent. The heterocyclization process was well-tolerated by a wide range of aryl, heteroaryl, and alkyl propargylamides. This protocol constitutes a valuable synthetic pathway to 5-oxazolecarbaldehydes, alternative to the formylation on oxazole rings, often unsatisfactory in term of regioselectivity and yields.