N-Phenyl-4,4-pentamethylene-5-vinyl-6-aza-2-oxacyclohexan-1-one | 145198-91-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂螺癸烷衍生物
• 英文名称: N-Phenyl-4,4-pentamethylene-5-vinyl-6-aza-2-oxacyclohexan-1-one
• 英文别名: 5-Ethenyl-4-phenyl-2-oxa-4-azaspiro[5.5]undecan-3-one
• CAS: 145198-91-0
• 化学式: C₁₇H₂₁NO₂
• 分子量: 271.359
• InChiKey: ADNZIONNOOETNM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4,4-Pentamethylene-3-vinyl-2,6-dioxacyclohexan-1-one 、 异氰酸苯酯 在 四(三苯基膦)钯 作用下， 以 1,4-二氧六环 为溶剂， 反应 11.0h， 以90%的产率得到N-Phenyl-4,4-pentamethylene-5-vinyl-6-aza-2-oxacyclohexan-1-one
  参考文献：
  名称：

  Palladium-catalysed regio- and stereo-selective synthesis of allylic amines

  摘要：

  3-乙烯基-2,6-二氧杂环己烷-1-酮 1 经 N-对甲基苯磺酰或 N-芳基异氰酸酯和催化量的 Pd0 处理后，以良好的收率和独特的立体选择性转化为 N-对甲基苯磺酰和 N-芳基-3-乙烯基-2-氮杂-6-氧杂环己烷-1-酮 2。

  DOI：

  10.1039/c39920001498

文献信息

• Regio- and Stereoselective Synthesis of 1,3-Hydroxyl Amines via Palladium-Catalyzed Carbonate-Carbamate Transformation with Unique Stereoselectivity: Synthesis of 3-Amino-4-penten-1-ols
  作者：Takashi Bando、Hiroto Harayama、Yoshimasa Fukazawa、Motoo Shiro、Keigo Fugami、Shuji Tanaka、Yoshinao Tamaru

  DOI：10.1021/jo00085a039

  日期：1994.3

  The transformation of cyclic carbonates 1 to cyclic carbamates 4 is achieved in the presence of aryl or sulfonyl isocyanate by the catalysis of Pd(0) in high yield and with high structural flexibility. The reaction shows unique stereoselectivity: 3,4-disubstituted carbonates 2, irrespective of the composition of their stereoisomers, provide trans-5 exclusively or predominantly over cis-5. Mixtures of cis- and trans-3,5-disubstituted carbonates 3 furnish either cis-6 or trans-6 in high selectivity depending on the reaction conditions (kinetic or thermodynamic control, respectively). H-1 NMR and X-ray structure analyses of 5 and 6 indicate that the stereochemical outcome is governed by an A1,2-strain between N-sulfonyl and C5-vinyl substituents.