2-tert-Butyl-3,3,4,4,6,6-hexamethyl-3,4,4a,5,6,7-hexahydro-indeno[7,1-bc]furan | 142672-80-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 2-tert-Butyl-3,3,4,4,6,6-hexamethyl-3,4,4a,5,6,7-hexahydro-indeno[7,1-bc]furan
• 英文别名: 3-Tert-butyl-5,5,6,6,9,9-hexamethyl-2-oxatricyclo[5.3.1.04,11]undeca-1(11),3-diene
• CAS: 142672-80-8
• 化学式: C₂₀H₃₂O
• 分子量: 288.473
• InChiKey: NGFDUTWQJIWXAQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  13.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-iodo-5,5-dimethylcyclohex-2-enone 在 四(三苯基膦)钯 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 40.0h， 生成 2-tert-Butyl-3,3,4,4,6,6-hexamethyl-3,4,4a,5,6,7-hexahydro-indeno[7,1-bc]furan
  参考文献：
  名称：

  Furans from Novel [3 + 2] Photocycloaddition of Alkenes to 2-(1-Alkynyl)cyclohexenones

  摘要：

  Photocycloaddition of 2-alkynyl-substituted cyclohexenones 8c-11c with isobutylene (2) and tetramethylethylene (3a) leads to tricyclic furans 15a-18a and 15b-17b; respectively, in gas chromatographic yields of similar to 90%. A suggested mechanism for this novel-process is shown in eq 2. Tetramethoxyethylene (3b) gives only oxetanes 22 and 23, and the 3-methyl-substituted ketone 12c fails to react with 2 and 3a,b. tert-Butylethylene gives [2 + 2] adduct 24 with 10c.

  DOI：

  10.1021/jo00097a049

文献信息

• Tetrasubstituted furans from photocycloaddition of alkenes to 2-(1-alkynyl)cyclohexenones
  作者：Paul Margaretha、Stefan Reichow、William C. Agosta

  DOI：10.1039/c39920000797

  日期：——

  Photocycloaddition of 2-(1-alkynyl)cyclohexenones 1 and 2 with alkenes 3 and 4 furnishes tetrasubstituted furans 5–8 as the only isolated products; a suggested mechanism leads from the alkyl propynyl biradical 12 to carbene 13, which then closes to the furan.

  2-（1-炔基）的光致环己烯酮1和2与烯烃3和4种配料四取代呋喃5 - 8作为唯一的分离产品; 一种建议的机理是从烷基丙炔基双自由基12到达卡宾13，然后卡宾13靠近呋喃。
• Furans from Novel [3 + 2] Photocycloaddition of Alkenes to 2-(1-Alkynyl)cyclohexenones
  作者：Paul Margaretha、William C. Agosta、Stefan Reichow

  DOI：10.1021/jo00097a049

  日期：1994.9

  Photocycloaddition of 2-alkynyl-substituted cyclohexenones 8c-11c with isobutylene (2) and tetramethylethylene (3a) leads to tricyclic furans 15a-18a and 15b-17b; respectively, in gas chromatographic yields of similar to 90%. A suggested mechanism for this novel-process is shown in eq 2. Tetramethoxyethylene (3b) gives only oxetanes 22 and 23, and the 3-methyl-substituted ketone 12c fails to react with 2 and 3a,b. tert-Butylethylene gives [2 + 2] adduct 24 with 10c.