1-(4-Methoxy-phenyl)-2-((1S,4aS,8aS)-5,5,8a-trimethyl-2-methylene-decahydro-naphthalen-1-yl)-ethanone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4-Methoxy-phenyl)-2-((1S,4aS,8aS)-5,5,8a-trimethyl-2-methylene-decahydro-naphthalen-1-yl)-ethanone
• 英文别名: 2-[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-1-(4-methoxyphenyl)ethanone
• 化学式: C₂₃H₃₂O₂
• 分子量: 340.506
• InChiKey: BOILWFIPFCGMCC-IEIRFRATSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(4-Methoxy-phenyl)-2-((1S,4aS,8aS)-5,5,8a-trimethyl-2-methylene-decahydro-naphthalen-1-yl)-ethanone 以 乙腈 为溶剂， 反应 0.5h， 以95%的产率得到[(4aS,8aS,8bR)-2-(4-Methoxy-phenyl)-5,5,8a-trimethyl-4,4a,5,6,7,8,8a,8b-octahydro-3H-cyclobuta[a]naphthalen-2a-yl]-methanol
  参考文献：
  名称：

  Photochemical Access to Tetra- and Pentacyclic Terpene-like Products from R-(+)-Sclareolide

  摘要：

  Fused tetracyclic oxetanes 4, highly substituted cyclobutenes 6, and the pentacyclic derivatives 7 and 8 were obtained by irradiation of derivatives 3 that were prepared from commercial R-(+)-sclareolide (1) in three steps. Compounds 4 are formed through a Paterno-Buchi reaction, while tricyclic derivatives 6 are the fragmentation products of the first formed oxetanes. In clear contrast, cyclopentenyl and 3-furyl derivatives, 3e and 3f, gave the [2+2] adducts, namely pentacyclic derivatives 7 and 8. All the reported reactions are totally regio- and stereoselective, with the exception of the cyclization of furyl derivative 3f, which gave the mixture of both the crossed (7b) and the right (8) isomers.

  DOI：

  10.1021/jo034177y
• 作为产物：
  描述：

  4-溴苯甲醚 、 N-methoxy-N-methyl-2-((1S,4aS,8aS)-5,5,8a-trimethyl-2-methylenedecahydronaphthalen-1-yl)acetamide 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 以80%的产率得到1-(4-Methoxy-phenyl)-2-((1S,4aS,8aS)-5,5,8a-trimethyl-2-methylene-decahydro-naphthalen-1-yl)-ethanone
  参考文献：
  名称：

  Photochemical Access to Tetra- and Pentacyclic Terpene-like Products from R-(+)-Sclareolide

  摘要：

  Fused tetracyclic oxetanes 4, highly substituted cyclobutenes 6, and the pentacyclic derivatives 7 and 8 were obtained by irradiation of derivatives 3 that were prepared from commercial R-(+)-sclareolide (1) in three steps. Compounds 4 are formed through a Paterno-Buchi reaction, while tricyclic derivatives 6 are the fragmentation products of the first formed oxetanes. In clear contrast, cyclopentenyl and 3-furyl derivatives, 3e and 3f, gave the [2+2] adducts, namely pentacyclic derivatives 7 and 8. All the reported reactions are totally regio- and stereoselective, with the exception of the cyclization of furyl derivative 3f, which gave the mixture of both the crossed (7b) and the right (8) isomers.

  DOI：

  10.1021/jo034177y

文献信息

• Photochemical Access to Tetra- and Pentacyclic Terpene-like Products from <i>R</i>-(+)-Sclareolide
  作者：María C. de la Torre、Isabel García、Miguel A. Sierra

  DOI：10.1021/jo034177y

  日期：2003.8.1

  Fused tetracyclic oxetanes 4, highly substituted cyclobutenes 6, and the pentacyclic derivatives 7 and 8 were obtained by irradiation of derivatives 3 that were prepared from commercial R-(+)-sclareolide (1) in three steps. Compounds 4 are formed through a Paterno-Buchi reaction, while tricyclic derivatives 6 are the fragmentation products of the first formed oxetanes. In clear contrast, cyclopentenyl and 3-furyl derivatives, 3e and 3f, gave the [2+2] adducts, namely pentacyclic derivatives 7 and 8. All the reported reactions are totally regio- and stereoselective, with the exception of the cyclization of furyl derivative 3f, which gave the mixture of both the crossed (7b) and the right (8) isomers.