(2R,4S,6R,6aS,8aR,9S,9aR)-2,4-dimethyl-3,4,6,6a,8a,9-hexahydro-2H-6,9-methanocyclopropa[1,5]cyclopenta[1,2-b][1,5]dioxocine | 724774-18-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,4S,6R,6aS,8aR,9S,9aR)-2,4-dimethyl-3,4,6,6a,8a,9-hexahydro-2H-6,9-methanocyclopropa[1,5]cyclopenta[1,2-b][1,5]dioxocine
• CAS: 724774-18-9
• 化学式: C₁₃H₁₈O₂
• 分子量: 206.285
• InChiKey: WPGMUIHXYFNKGD-RWIORTIOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.14
• 重原子数：
  15.0
• 可旋转键数：
  0.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (2R,4S,6R,6aS,8aR,9S,9aR)-2,4-dimethyl-3,4,6,6a,8a,9-hexahydro-2H-6,9-methanocyclopropa[1,5]cyclopenta[1,2-b][1,5]dioxocine 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 水 、 乙酸乙酯 、 丙酮 为溶剂， 反应 20.0h， 生成 (1R,5S,6R)-6-((1S,3R)-3-Hydroxy-1-methyl-butoxy)-bicyclo[3.2.1]octan-8-one
  参考文献：
  名称：

  Asymmetric meta-arene–alkene photocycloaddition controlled by a 2,4-pentanediol tether

  摘要：

  Photo-irradiation of a substrate having phenyl and vinyl groups resulted in a stereocontrolled meta-arene-alkene cycloaddition when the two groups were connected by a chiral 2,4-pentanediol tether. The regioselectivity during the ring closing step after the initial addition was dependent on the stereochemistry of the tether and the photolysis conditions. The substrate bearing a p-tolyl or 3,5-xylyl group instead of the phenyl also underwent strict stereocontrolled addition. In the case of the o- and m-tolyl substrates, the regioselectivity due to the unsymmetric substitution of the arene moiety was also fully controlled. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.03.017
• 作为产物：
  描述：

  (2R,4S)-2,4-pentanediol 以 正戊烷 为溶剂， 生成 (2R,4S,6R,6aS,8aR,9S,9aR)-2,4-dimethyl-3,4,6,6a,8a,9-hexahydro-2H-6,9-methanocyclopropa[1,5]cyclopenta[1,2-b][1,5]dioxocine 、
  参考文献：
  名称：

  Asymmetric meta-arene–alkene photocycloaddition controlled by a 2,4-pentanediol tether

  摘要：

  Photo-irradiation of a substrate having phenyl and vinyl groups resulted in a stereocontrolled meta-arene-alkene cycloaddition when the two groups were connected by a chiral 2,4-pentanediol tether. The regioselectivity during the ring closing step after the initial addition was dependent on the stereochemistry of the tether and the photolysis conditions. The substrate bearing a p-tolyl or 3,5-xylyl group instead of the phenyl also underwent strict stereocontrolled addition. In the case of the o- and m-tolyl substrates, the regioselectivity due to the unsymmetric substitution of the arene moiety was also fully controlled. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.03.017

文献信息

• Asymmetric meta-arene–alkene photocycloaddition controlled by a 2,4-pentanediol tether
  作者：Kazutake Hagiya、Akiko Yamasaki、Tadashi Okuyama、Takashi Sugimura

  DOI：10.1016/j.tetasy.2004.03.017

  日期：2004.5

  Photo-irradiation of a substrate having phenyl and vinyl groups resulted in a stereocontrolled meta-arene-alkene cycloaddition when the two groups were connected by a chiral 2,4-pentanediol tether. The regioselectivity during the ring closing step after the initial addition was dependent on the stereochemistry of the tether and the photolysis conditions. The substrate bearing a p-tolyl or 3,5-xylyl group instead of the phenyl also underwent strict stereocontrolled addition. In the case of the o- and m-tolyl substrates, the regioselectivity due to the unsymmetric substitution of the arene moiety was also fully controlled. (C) 2004 Elsevier Ltd. All rights reserved.