Dihydro-3-cyclohexyl-5-methyl-6,6-diphenyl-1,2,4,5-trioxazine | 139632-98-7

• 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: Dihydro-3-cyclohexyl-5-methyl-6,6-diphenyl-1,2,4,5-trioxazine
• 英文别名: 3-cyclohexyl-5-methyl-6,6-diphenyl-1,2,4,5-trioxazinane
• CAS: 139632-98-7
• 化学式: C₂₁H₂₅NO₃
• 分子量: 339.434
• InChiKey: AHKZLQZJPDHPBZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  30.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-(二苯基亚甲基)甲胺N-氧化物 、 trans-2-cyclohexyl-1-methoxyethylene 在 臭氧 作用下， 以 二氯甲烷 为溶剂， 以97%的产率得到Dihydro-3-cyclohexyl-5-methyl-6,6-diphenyl-1,2,4,5-trioxazine
  参考文献：
  名称：

  Synthesis and x-ray analysis of dihydro-1,2,4,5-trioxazine. Evidence of a stepwise mechanism for the [3 + 3] cycloaddition of carbonyl oxides with nitrones

  摘要：

  Carbonyl oxides, derived by ozonolysis of vinyl ethers, readily undergo [3 + 3] cycloaddition reactions with nitrones affording dihydro-1,2,4,5-trioxazines in fair to excellent yield. The structures of dihydro-3,5,6-triphenyl-1,2,4,5-trioxazine (5f) and dihydro-3-cyclohexyl-5-methyl-6,6-diphenyl-1,2,4,5-trioxazine (5t) were unambiguously determined by X-ray analysis. Ozonolysis of 1-cyclohexyl-2-methoxyethene in the presence of either (E)- or (Z)-alpha-(4-methylphenyl)-alpha-phenyl-N-methylnitrone gave a 1:1 mixture of two stereoisomeric cycloadducts. This result, in conjunction with the structure of the relevant 5t, suggests that the [3 + 3] cycloaddition proceeds by a stepwise mechanism.

  DOI：

  10.1021/jo00034a018

文献信息

• Synthesis and x-ray analysis of dihydro-1,2,4,5-trioxazine. Evidence of a stepwise mechanism for the [3 + 3] cycloaddition of carbonyl oxides with nitrones
  作者：Mitsuyuki Mori、Tomohito Sugiyama、Masatomo Nojima、Shigekazu Kusabayashi、Kevin J. McCullough

  DOI：10.1021/jo00034a018

  日期：1992.4

  Carbonyl oxides, derived by ozonolysis of vinyl ethers, readily undergo [3 + 3] cycloaddition reactions with nitrones affording dihydro-1,2,4,5-trioxazines in fair to excellent yield. The structures of dihydro-3,5,6-triphenyl-1,2,4,5-trioxazine (5f) and dihydro-3-cyclohexyl-5-methyl-6,6-diphenyl-1,2,4,5-trioxazine (5t) were unambiguously determined by X-ray analysis. Ozonolysis of 1-cyclohexyl-2-methoxyethene in the presence of either (E)- or (Z)-alpha-(4-methylphenyl)-alpha-phenyl-N-methylnitrone gave a 1:1 mixture of two stereoisomeric cycloadducts. This result, in conjunction with the structure of the relevant 5t, suggests that the [3 + 3] cycloaddition proceeds by a stepwise mechanism.