4-methoxytriphenylacetonitrile oxide | 137003-25-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 4-methoxytriphenylacetonitrile oxide
• 英文别名: 2-(4-Methoxyphenyl)-2,2-diphenylacetonitrile oxide；2-(4-methoxyphenyl)-2,2-diphenylacetonitrile oxide
• CAS: 137003-25-9
• 化学式: C₂₁H₁₇NO₂
• 分子量: 315.371
• InChiKey: AYHXDGVGEFZQJH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  39.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-methoxytriphenylacetonitrile oxide 以 xylene 为溶剂， 生成
  参考文献：
  名称：

  A kinetic study of the rearrangement of triarylacetonitrile oxides

  摘要：

  The thermal rearrangement of triphenylacetonitrile oxide (1a) to triphenylmethyl isocyanate (2) is a first-order process. Rate constants at five temperatures between 116 and 190-degrees-C were determined giving DELTA-H double-ended dagger = 9.3 +/- 1.1 kcal/mol and DELTA-S double-ended dagger = -58.2 +/- 2.4 cal/mol.K. The rearrangement of substituted triarylacetonitrile oxides (1b-d) occur only slightly faster than that of 1a. These results are interpreted in terms of a concerted single-step rearrangement in which the highly ordered transition state (6c) has a degree of radical character.

  DOI：

  10.1021/jo00026a024
• 作为产物：
  描述：

  4-溴苯甲醚 在 magnesium 、 乙酰氯 作用下， 以 甲苯 、 苯 为溶剂， 反应 1.5h， 生成 4-methoxytriphenylacetonitrile oxide
  参考文献：
  名称：

  A kinetic study of the rearrangement of triarylacetonitrile oxides

  摘要：

  The thermal rearrangement of triphenylacetonitrile oxide (1a) to triphenylmethyl isocyanate (2) is a first-order process. Rate constants at five temperatures between 116 and 190-degrees-C were determined giving DELTA-H double-ended dagger = 9.3 +/- 1.1 kcal/mol and DELTA-S double-ended dagger = -58.2 +/- 2.4 cal/mol.K. The rearrangement of substituted triarylacetonitrile oxides (1b-d) occur only slightly faster than that of 1a. These results are interpreted in terms of a concerted single-step rearrangement in which the highly ordered transition state (6c) has a degree of radical character.

  DOI：

  10.1021/jo00026a024

文献信息

• A kinetic study of the rearrangement of triarylacetonitrile oxides
  作者：Leslie W. Gibbs、Donald K. Wedegaertner

  DOI：10.1021/jo00026a024

  日期：1991.12

  The thermal rearrangement of triphenylacetonitrile oxide (1a) to triphenylmethyl isocyanate (2) is a first-order process. Rate constants at five temperatures between 116 and 190-degrees-C were determined giving DELTA-H double-ended dagger = 9.3 +/- 1.1 kcal/mol and DELTA-S double-ended dagger = -58.2 +/- 2.4 cal/mol.K. The rearrangement of substituted triarylacetonitrile oxides (1b-d) occur only slightly faster than that of 1a. These results are interpreted in terms of a concerted single-step rearrangement in which the highly ordered transition state (6c) has a degree of radical character.