1-phenyl-2,2,2-trifluoro-1-<4-(1-triphenylmethyl)imidazole>ethyl phenyl thionocarbonate | 161530-08-1

• 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: 1-phenyl-2,2,2-trifluoro-1-<4-(1-triphenylmethyl)imidazole>ethyl phenyl thionocarbonate
• 英文别名: Imidazole, 4-[alpha-phenyloxythiocarboxy-alpha-trifluoromethylbenzyl]-；phenoxy-[2,2,2-trifluoro-1-phenyl-1-(1-tritylimidazol-4-yl)ethoxy]methanethione
• CAS: 161530-08-1
• 化学式: C₃₇H₂₇F₃N₂O₂S
• 分子量: 620.695
• InChiKey: ANEJNAWAIZVIGJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.7
• 重原子数：
  45
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  68.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-phenyl-2,2,2-trifluoro-1-<4-(1-triphenylmethyl)imidazole>ethyl phenyl thionocarbonate 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以94%的产率得到4-(1-phenyl-2,2,2-trifluoroethyl)-<1-(triphenylmethyl)>imidazole
  参考文献：
  名称：

  Imidazole-assisted Intramolecular Phenoxythio Carbonylation of Tertiary Alcohols A Key Reactiob for the Deoxygenation od a-Trifluoromethylarylmethyl Alcohols

  摘要：

  The deoxygenation of alpha-trifluoromethylarylmethyl alcohols failed under catalytic hydrogenation conditions. However, these alcohols can be deoxygenated via their thionocarbonate intermediates followed by homolytic reductive cleavage of the C-O bond. The formation of the phenyl thionocarbonate esters is sterically dependent. Consequently, secondary alpha-trifluoromethyl arylmethyl alcohols can be smoothly converted to thionocarbonates, but tertiary alcohols cannot. Exceptions to this lack of reactivity are the aryl 4-substituted imidazolyl trifluoromethyl carbinols, which do form the thionocarbonates under these conditions.

  DOI：

  10.3987/com-94-s(b)77
• 作为产物：
  描述：

  1-三苯甲基-4-碘咪唑 在 4-二甲氨基吡啶 、 乙基溴化镁 作用下， 以 二氯甲烷 为溶剂， 反应 32.5h， 生成 1-phenyl-2,2,2-trifluoro-1-<4-(1-triphenylmethyl)imidazole>ethyl phenyl thionocarbonate
  参考文献：
  名称：

  Imidazole-assisted Intramolecular Phenoxythio Carbonylation of Tertiary Alcohols A Key Reactiob for the Deoxygenation od a-Trifluoromethylarylmethyl Alcohols

  摘要：

  The deoxygenation of alpha-trifluoromethylarylmethyl alcohols failed under catalytic hydrogenation conditions. However, these alcohols can be deoxygenated via their thionocarbonate intermediates followed by homolytic reductive cleavage of the C-O bond. The formation of the phenyl thionocarbonate esters is sterically dependent. Consequently, secondary alpha-trifluoromethyl arylmethyl alcohols can be smoothly converted to thionocarbonates, but tertiary alcohols cannot. Exceptions to this lack of reactivity are the aryl 4-substituted imidazolyl trifluoromethyl carbinols, which do form the thionocarbonates under these conditions.

  DOI：

  10.3987/com-94-s(b)77

文献信息

• Hsu Fu-Lian, Zhang Xiaoyan, Hong Seoung-Soo, Berg Frederic J., Miller Dua+, Heterocycles, 39 (1994) N 2, S 801-809
  作者：Hsu Fu-Lian, Zhang Xiaoyan, Hong Seoung-Soo, Berg Frederic J., Miller Dua+

  DOI：——

  日期：——
• Imidazole-assisted Intramolecular Phenoxythio Carbonylation of Tertiary Alcohols A Key Reactiob for the Deoxygenation od a-Trifluoromethylarylmethyl Alcohols
  作者：Fu-Lian Hsu、Xiaoyan Zhang、Seoung-Soo Hong、Frederic J. Berg、Duane D. Miller

  DOI：10.3987/com-94-s(b)77

  日期：——

  The deoxygenation of alpha-trifluoromethylarylmethyl alcohols failed under catalytic hydrogenation conditions. However, these alcohols can be deoxygenated via their thionocarbonate intermediates followed by homolytic reductive cleavage of the C-O bond. The formation of the phenyl thionocarbonate esters is sterically dependent. Consequently, secondary alpha-trifluoromethyl arylmethyl alcohols can be smoothly converted to thionocarbonates, but tertiary alcohols cannot. Exceptions to this lack of reactivity are the aryl 4-substituted imidazolyl trifluoromethyl carbinols, which do form the thionocarbonates under these conditions.