cis-N-(p-Toluenesulfonyl)-5-benzyl-4-vinyl-3-aza-1-oxacyclohexane

• 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: cis-N-(p-Toluenesulfonyl)-5-benzyl-4-vinyl-3-aza-1-oxacyclohexane
• 化学式: C₂₀H₂₃NO₃S
• 分子量: 357.474
• InChiKey: ZPADVSZSFNOKCA-UYAOXDASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.39
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  46.61
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  5-benzyl-4-vinyl-1,3-dioxan-2-one 在 四(三苯基膦)钯 氢氧化钾 、 硫酸 作用下， 以 1,4-二氧六环 、 乙醇 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 cis-N-(p-Toluenesulfonyl)-5-benzyl-4-vinyl-3-aza-1-oxacyclohexane
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1021/jo00085a039

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.