4-(6-Chloro-benzo[1,3]dioxol-5-ylmethyl)-[1,2,4]triazole-3,5-dione | 864278-43-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 4-(6-Chloro-benzo[1,3]dioxol-5-ylmethyl)-[1,2,4]triazole-3,5-dione
• CAS: 864278-43-3
• 化学式: C₁₀H₆ClN₃O₄
• 分子量: 267.628
• InChiKey: LZPCAYPWRUSELT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.58
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  80.56
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-(6-Chloro-benzo[1,3]dioxol-5-ylmethyl)-[1,2,4]triazole-3,5-dione 在 platinum(IV) oxide 氢氟酸 、 氢气 、 溶剂黄146 作用下， 以 水 、 乙酸乙酯 、 甲苯 、 乙腈 为溶剂， 反应 123.0h， 生成 (5aS,6aR,7aS,8S,8aR)-2-(6-Chloro-benzo[1,3]dioxol-5-ylmethyl)-8-hydroxy-hexahydro-7-oxa-2,3a,8b-triaza-cyclopenta[a]cyclopropa[g]naphthalene-1,3,6-trione 6-(O-isobutyl-oxime)
  参考文献：
  名称：

  Stereocontrolled Synthesis of a Complex Library via Elaboration of Angular Epoxyquinol Scaffolds

  摘要：

  We have accomplished the synthesis of a complex chemical library via elaboration of angular epoxyquinol scaffolds with distinct skeletal frameworks. The key strategy involves highly stereocontrolled [4 + 2] Diels-Alder cycloadditions of chiral, nonracemic epoxyquinol dienes to generate the scaffolds. Further scaffold diversification involves hydrogenation, epimerization, dehydration, and condensation of the carbonyl group with alkoxyamine and carbazate building blocks. Further elaboration of the scaffolds also provided new skeletal frameworks using hydroxyl-directed Diels-Alder cycloaddition and reductive N-N bond cleavage. The overall process afforded 244 highly complex and functionalized compounds. Preliminary biological screening of the library uncovered six compounds which showed significant inhibition of Hsp 72 induction.

  DOI：

  10.1021/jo050956y
• 作为产物：
  描述：

  4-[(2H-1,3-Benzodioxol-5-yl)methyl]-1,2,4-triazolidine-3,5-dione 在 三氯异氰尿酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以90%的产率得到4-(6-Chloro-benzo[1,3]dioxol-5-ylmethyl)-[1,2,4]triazole-3,5-dione
  参考文献：
  名称：

  Stereocontrolled Synthesis of a Complex Library via Elaboration of Angular Epoxyquinol Scaffolds

  摘要：

  We have accomplished the synthesis of a complex chemical library via elaboration of angular epoxyquinol scaffolds with distinct skeletal frameworks. The key strategy involves highly stereocontrolled [4 + 2] Diels-Alder cycloadditions of chiral, nonracemic epoxyquinol dienes to generate the scaffolds. Further scaffold diversification involves hydrogenation, epimerization, dehydration, and condensation of the carbonyl group with alkoxyamine and carbazate building blocks. Further elaboration of the scaffolds also provided new skeletal frameworks using hydroxyl-directed Diels-Alder cycloaddition and reductive N-N bond cleavage. The overall process afforded 244 highly complex and functionalized compounds. Preliminary biological screening of the library uncovered six compounds which showed significant inhibition of Hsp 72 induction.

  DOI：

  10.1021/jo050956y