3,4,5,5a-tetrahydroxantheno[9,1-cd]isoxazole | 1620398-70-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 3,4,5,5a-tetrahydroxantheno[9,1-cd]isoxazole
• 英文别名: 8,14-Dioxa-15-azatetracyclo[7.6.1.02,7.013,16]hexadeca-1(15),2,4,6,13(16)-pentaene；8,14-dioxa-15-azatetracyclo[7.6.1.02,7.013,16]hexadeca-1(15),2,4,6,13(16)-pentaene
• CAS: 1620398-70-0
• 化学式: C₁₃H₁₁NO₂
• 分子量: 213.236
• InChiKey: ODJZUISLQQOFBI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  35.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,4,5,5a-tetrahydroxantheno[9,1-cd]isoxazole 在 氢气 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以98%的产率得到9-amino-2,3,4,4a-tetrahydro-1H-xanthen-1-one
  参考文献：
  名称：

  Annulated Isoxazoles via [3 + 2] Cycloaddition of Alkenyl Bromides and Oximoyl Chlorides and Ag(I) Promoted Elimination

  摘要：

  Substituted salicylaldehydes are converted to fused tetracyclic isoxazoles through a synthetic sequence incorporating substitution of 2-bromo-2-cyclohexen-1-ol, formation of an oxime function, conversion to an oximoyl chloride, intramolecular [3 + 2] cycloaddition, and elimination of an equivalent of hydrogen bromide using silver(I) carbonate. Six examples of this sequence are presented.

  DOI：

  10.1021/jo501376q
• 作为产物：
  描述：

  2-bromocyclohex-2-en-1-ol 在 吡啶 、 N-氯代丁二酰亚胺 、 羟胺 、 三乙胺 、 silver carbonate 、 甲基磺酸酐 作用下， 以 二氯甲烷 、 氯仿 、 水 、 二甲基亚砜 为溶剂， 反应 39.5h， 生成 3,4,5,5a-tetrahydroxantheno[9,1-cd]isoxazole
  参考文献：
  名称：

  Annulated Isoxazoles via [3 + 2] Cycloaddition of Alkenyl Bromides and Oximoyl Chlorides and Ag(I) Promoted Elimination

  摘要：

  Substituted salicylaldehydes are converted to fused tetracyclic isoxazoles through a synthetic sequence incorporating substitution of 2-bromo-2-cyclohexen-1-ol, formation of an oxime function, conversion to an oximoyl chloride, intramolecular [3 + 2] cycloaddition, and elimination of an equivalent of hydrogen bromide using silver(I) carbonate. Six examples of this sequence are presented.

  DOI：

  10.1021/jo501376q

文献信息

• Annulated Isoxazoles via [3 + 2] Cycloaddition of Alkenyl Bromides and Oximoyl Chlorides and Ag(I) Promoted Elimination
  作者：Emmanuel B. Castillo-Contreras、Alexander M. Stahl、Gregory R. Dake

  DOI：10.1021/jo501376q

  日期：2014.8.1

  Substituted salicylaldehydes are converted to fused tetracyclic isoxazoles through a synthetic sequence incorporating substitution of 2-bromo-2-cyclohexen-1-ol, formation of an oxime function, conversion to an oximoyl chloride, intramolecular [3 + 2] cycloaddition, and elimination of an equivalent of hydrogen bromide using silver(I) carbonate. Six examples of this sequence are presented.