2-Chloro-4-(trifluoromethoxy)phenyl isocyanate | 79960-69-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-Chloro-4-(trifluoromethoxy)phenyl isocyanate
• 英文别名: 2-chloro-1-isocyanato-4-(trifluoromethoxy)benzene
• CAS: 79960-69-3
• 化学式: C₈H₃ClF₃NO₂
• 分子量: 237.566
• InChiKey: LXGXKVLGHHEBAR-UHFFFAOYSA-N

物化性质

• 沸点：
  213.9±40.0 °C(Predicted)
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,5-二氧杂螺[5.5]十一烷-2,4-二酮 、 2-Chloro-4-(trifluoromethoxy)phenyl isocyanate 在 三乙胺 作用下， 以60%的产率得到N-[2-chloro-4-(trifluoromethoxy)phenyl]-2-hydroxy-4-oxo-1,5-dioxaspiro[5.5]undec-2-ene-3-carboxamide
  参考文献：
  名称：

  A new class of inhibitors of secretory phospholipase A2: enolized 1,3-dioxane-4,6-dione-5-carboxamides

  摘要：

  Enolized 1,3-dioxane-4,6-dione-5-carboxamides a were identified as a new class of inhibitors of secretory phospholipase A(2) from human polymorphonuclear leucocytes (h-PMN PLA(2)). Among the more than 30 compounds synthesized, the most potent inhibitors (IC50 0.6-10 mu M) were found in the series of 2,4-disubstituted phenyl analogues of a. Compound 1a was selected for evaluation of its biological profile. This substance potently inhibited secretory PLA(2)s from several sources other than human PMNs, with a clear preference for group II over group I PLA(2), whereas human cytosolic PLA(2) and phospholipase C were not significantly affected. Inhibition of h-PMN PLA(2) was calcium-dependent. In intact mammalian cells stimulated in vitro, the release of arachidonic acid and the generation of prostaglandins and leukotrienes were inhibited at concentrations compatible with inhibition of PLA(2) as an underlying mechanism. In animal models in vivo (carragheenan oedema, adjuvant arthritis, pertussis pleurisy) 1a showed antiinflammatory activity, although the effect was rather weak compared with standard reference compounds.

  DOI：

  10.1016/0223-5234(94)90026-4
• 作为产物：
  描述：

  三光气 、 2-氯-4-三氟甲氧基苯胺 以 1,4-二氧六环 为溶剂， 反应 5.0h， 生成 2-Chloro-4-(trifluoromethoxy)phenyl isocyanate
  参考文献：
  名称：

  A new class of inhibitors of secretory phospholipase A2: enolized 1,3-dioxane-4,6-dione-5-carboxamides

  摘要：

  Enolized 1,3-dioxane-4,6-dione-5-carboxamides a were identified as a new class of inhibitors of secretory phospholipase A(2) from human polymorphonuclear leucocytes (h-PMN PLA(2)). Among the more than 30 compounds synthesized, the most potent inhibitors (IC50 0.6-10 mu M) were found in the series of 2,4-disubstituted phenyl analogues of a. Compound 1a was selected for evaluation of its biological profile. This substance potently inhibited secretory PLA(2)s from several sources other than human PMNs, with a clear preference for group II over group I PLA(2), whereas human cytosolic PLA(2) and phospholipase C were not significantly affected. Inhibition of h-PMN PLA(2) was calcium-dependent. In intact mammalian cells stimulated in vitro, the release of arachidonic acid and the generation of prostaglandins and leukotrienes were inhibited at concentrations compatible with inhibition of PLA(2) as an underlying mechanism. In animal models in vivo (carragheenan oedema, adjuvant arthritis, pertussis pleurisy) 1a showed antiinflammatory activity, although the effect was rather weak compared with standard reference compounds.

  DOI：

  10.1016/0223-5234(94)90026-4

文献信息

• Synthesis and Anthelmintic Activity of 7-Hydroxy- 5-oxo-5<i>H</i>-thieno[3,2-<i>b</i>]pyran-6-carboxanilides and -6-thiocarboxanilides
  作者：Andrew Plant、Achim Harder、Norbert Mencke、Heinz-Jürgen Bertram

  DOI：10.1002/(sici)1096-9063(199612)48:4<351::aid-ps485>3.0.co;2-t

  日期：1996.12

  7-Hydroxy-5-oxo-5H-thieno [3,2-b]pyran-6-carboxanilides and -6-thiocarboxanilides represent a novel series of anthelmintic compounds, with broad-spectrum activity against important parasitic nematodes in sheep and dogs. In particular, an improved efficacy against Trichostrongylus colubriformis in sheep over the related 3-carbamoyl-4-hydroxycoumarins has been noted. New synthetic routes to the key intermediate, 7-hydroxythieno[3,2-b]pyran-5-one, have been developed.
• Substituierte 5-Phenylcarbamoyl-barbitursäuren, Verfahren zu ihrer Herstellung und ihre Verwendung als Insektizide
  申请人：BAYER AG

  公开号：EP0007541B1

  公开（公告）日：1981-09-09
• US4239762A
  申请人：——

  公开号：US4239762A

  公开（公告）日：1980-12-16
• A new class of inhibitors of secretory phospholipase A2: enolized 1,3-dioxane-4,6-dione-5-carboxamides
  作者：W Breitenstein、F Märki、S Roggo、I Wiesenberg、J Pfeilschifter、P Furet、E Beriger

  DOI：10.1016/0223-5234(94)90026-4

  日期：1994.1

  Enolized 1,3-dioxane-4,6-dione-5-carboxamides a were identified as a new class of inhibitors of secretory phospholipase A(2) from human polymorphonuclear leucocytes (h-PMN PLA(2)). Among the more than 30 compounds synthesized, the most potent inhibitors (IC50 0.6-10 mu M) were found in the series of 2,4-disubstituted phenyl analogues of a. Compound 1a was selected for evaluation of its biological profile. This substance potently inhibited secretory PLA(2)s from several sources other than human PMNs, with a clear preference for group II over group I PLA(2), whereas human cytosolic PLA(2) and phospholipase C were not significantly affected. Inhibition of h-PMN PLA(2) was calcium-dependent. In intact mammalian cells stimulated in vitro, the release of arachidonic acid and the generation of prostaglandins and leukotrienes were inhibited at concentrations compatible with inhibition of PLA(2) as an underlying mechanism. In animal models in vivo (carragheenan oedema, adjuvant arthritis, pertussis pleurisy) 1a showed antiinflammatory activity, although the effect was rather weak compared with standard reference compounds.