(Z)-2-(tert-butyl)-3a,4,5,6-tetrahydro-3a,5,5-trimethyl-3-[4-(trimethylsilyl)but-1-en-3-ynyl]pyrrolo[1,2-b]isoxazole | 428516-84-1

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (Z)-2-(tert-butyl)-3a,4,5,6-tetrahydro-3a,5,5-trimethyl-3-[4-(trimethylsilyl)but-1-en-3-ynyl]pyrrolo[1,2-b]isoxazole
• 英文别名: [(Z)-4-(2-tert-butyl-3a,5,5-trimethyl-4,6-dihydropyrrolo[1,2-b][1,2]oxazol-3-yl)but-3-en-1-ynyl]-trimethylsilane
• CAS: 428516-84-1
• 化学式: C₂₀H₃₃NOSi
• 分子量: 331.574
• InChiKey: CNSMUIFXXXWOHM-BENRWUELSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.16
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z)-2-(tert-butyl)-3a,4,5,6-tetrahydro-3a,5,5-trimethyl-3-[4-(trimethylsilyl)but-1-en-3-ynyl]pyrrolo[1,2-b]isoxazole 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以92%的产率得到(Z)-3-(but-1-en-3-ynyl)-2-(tert-butyl)-3a,4,5,6-tetrahydro-3a,5,5-trimethylpyrrolo[1,2-b]isoxazole
  参考文献：
  名称：

  4-取代的 2,3-二氢异恶唑作为掩蔽的甲亚胺叶立德：通过烯基衍生物的 1,5-和 1,7-偶极电环化获得吡咯衍生物

  摘要：

  The enynyl-substituted 2,3-dihydroisoxazoles ('isoxazolines') 9-14 were prepared by highly (Z)-selective Peterson olefination reaction from the corresponding carbaldehydes 6-8. On short-time thermolysis (280-406degrees/10 s) the TMS derivatives 9-11 give rise to the annulated pyrrolines 18-20, which, in some cases. suffer CH4 elimination affording the pyrroles 15-17 In contrast. thermolysis of the terminal alkyne derivatives 12-14 leads to the bicyclic compounds 21-23. The reaction pathways are discussed on the basis of the formation of conjugated azomethine ylides as key intermediates. which either undergo a 1,5-cyclization to 18-20 or a 1,7-ring-closure affording cycloallene intermediates of type V, which are further transformed into the azepino pyrroles, 21-23.

  DOI：

  10.1002/1522-2675(20011219)84:12<3822::aid-hlca3822>3.0.co;2-o
• 作为产物：
  描述：

  1,3-bis(trimethylsilyl)propyne 、 2-tert-butyl-3a,5,5-trimethyl-3a,4,5,6-tetrahydropyrrolo[1,2-b]isoxazole-3-carbaldehyde 在 titanium(IV) isopropylate 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.75h， 以86%的产率得到(Z)-2-(tert-butyl)-3a,4,5,6-tetrahydro-3a,5,5-trimethyl-3-[4-(trimethylsilyl)but-1-en-3-ynyl]pyrrolo[1,2-b]isoxazole
  参考文献：
  名称：

  4-取代的 2,3-二氢异恶唑作为掩蔽的甲亚胺叶立德：通过烯基衍生物的 1,5-和 1,7-偶极电环化获得吡咯衍生物

  摘要：

  The enynyl-substituted 2,3-dihydroisoxazoles ('isoxazolines') 9-14 were prepared by highly (Z)-selective Peterson olefination reaction from the corresponding carbaldehydes 6-8. On short-time thermolysis (280-406degrees/10 s) the TMS derivatives 9-11 give rise to the annulated pyrrolines 18-20, which, in some cases. suffer CH4 elimination affording the pyrroles 15-17 In contrast. thermolysis of the terminal alkyne derivatives 12-14 leads to the bicyclic compounds 21-23. The reaction pathways are discussed on the basis of the formation of conjugated azomethine ylides as key intermediates. which either undergo a 1,5-cyclization to 18-20 or a 1,7-ring-closure affording cycloallene intermediates of type V, which are further transformed into the azepino pyrroles, 21-23.

  DOI：

  10.1002/1522-2675(20011219)84:12<3822::aid-hlca3822>3.0.co;2-o