(Z)-3-(but-1-en-3-ynyl)-3a,4,5,6-tetrahydro-3a,5,5-trimethyl-2-phenylpyrrolo[1,2-b]isoxazole | 428516-92-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (Z)-3-(but-1-en-3-ynyl)-3a,4,5,6-tetrahydro-3a,5,5-trimethyl-2-phenylpyrrolo[1,2-b]isoxazole
• 英文别名: 3-[(Z)-but-1-en-3-ynyl]-3a,5,5-trimethyl-2-phenyl-4,6-dihydropyrrolo[1,2-b][1,2]oxazole
• CAS: 428516-92-1
• 化学式: C₁₉H₂₁NO
• 分子量: 279.382
• InChiKey: XECNRXOXJPWTJZ-SDQBBNPISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 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)-3-(but-1-en-3-ynyl)-3a,4,5,6-tetrahydro-3a,5,5-trimethyl-2-phenylpyrrolo[1,2-b]isoxazole 以 苯 为溶剂， 反应 0.67h， 以23%的产率得到[6-(but-1-en-3-yn-6-yl)-2,2,5-trimethyl-1-azabicyclo[3.1.0]hex-6-yl](phenyl)methanone
  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：

  3a,5,5-trimethyl-2-phenyl-3a,4,5,6-tetrahydropyrrolo[1,2-b]isoxazole-3-carbaldehyde 在 titanium(IV) isopropylate 、 正丁基锂 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 25.75h， 生成 (Z)-3-(but-1-en-3-ynyl)-3a,4,5,6-tetrahydro-3a,5,5-trimethyl-2-phenylpyrrolo[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

文献信息

• 4-Substituted 2,3-Dihydroisoxazoles as Masked Azomethine Ylides: Access to Pyrrole Derivatives by 1,5- and 1,7-Dipolar Electrocyclizations of Enynyl Derivatives
  作者：Wolfgang Friebolin、Wolfgang Eberbach

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

  日期：2001.12.19

  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.