N-(p-Chlorophenyl)-5-vinyl-6-aza-2-oxacyclohexan-1-one | 145198-88-5

• 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: N-(p-Chlorophenyl)-5-vinyl-6-aza-2-oxacyclohexan-1-one
• 英文别名: N-(p-chlorophenyl)-4-vinyl-1,3-oxazin-2-one；3-(4-Chlorophenyl)-4-ethenyl-1,3-oxazinan-2-one
• CAS: 145198-88-5
• 化学式: C₁₂H₁₂ClNO₂
• 分子量: 237.686
• InChiKey: FIXRUYSWCXZSKC-UHFFFAOYSA-N

物化性质

• 沸点：
  335.9±41.0 °C(Predicted)
• 密度：
  1.305±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  对氯苯异氰酸酯 、 4-vinyl-1,3-dioxan-2-one 在 四(三苯基膦)钯 作用下， 以 1,4-二氧六环 为溶剂， 反应 8.0h， 以84%的产率得到N-(p-Chlorophenyl)-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

• Palladium-catalysed regio- and stereo-selective synthesis of allylic amines
  作者：Yoshinao Tamaru、Takashi Bando、Youichi Kawamura、Kazuto Okamura、Zen-ichi Yoshida、Motoo Shiro

  DOI：10.1039/c39920001498

  日期：——

  3-Vinyl-2,6-dioxacyclohexan-1-ones 1, by treatment with N-tosyl or N-aryl isocyanates and a catalytic amount of Pd0, are converted into N-tosyl- and N-aryl-3-vinyl-2-aza-6-oxacyclohexan-1-ones 2 in good yields and with unique stereoselectivity.

  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。
• Synthesis of 1,3-Oxazine Derivatives by Palladium-Catalyzed Cycloaddition of Vinyloxetanes with Heterocumulenes. Completely Stereoselective Synthesis of Bicyclic 1,3-Oxazines
  作者：Chitchamai Larksarp、Howard Alper

  DOI：10.1021/jo990430b

  日期：1999.5.1

  1,3-Oxazines were prepared by palladium-phosphine-catalyzed cycloaddition reactions of vinyloxetanes with heterocumulenes. 4-Vinyl-1,3-oxazin-2-imines were obtained in fine yields by the reaction of 2-vinyloxetanes with carbodiimides in THF at rt for 12 h using 1.5 mol % Pd-2(dba)(3). CHCl3 and 3 mol % bidentate phosphine ligands (dppe or dppp). When isocyanates were utilized in the reaction, moderate to good yields of 4-vinyl-1,3-oxazin-2-ones were achieved within 1-2 h at rt. Palladium-catalyzed cycloaddition of fused-bicyclic vinyloxetanes with heterocumulenes proceeds in a highly stereoselective fashion affording only the cis-3-aza-1-oxo-9-vinyl[4.4.0]decane derivatives in 43-98% yield.
• 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.