3,3-dihydroperoxy4-(hydroxymethyl)-β-thujane | 1181843-99-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 3,3-dihydroperoxy4-(hydroxymethyl)-β-thujane
• 英文别名: [(1S,2S,5S)-3,3-dihydroperoxy-2-methyl-5-propan-2-yl-2-bicyclo[3.1.0]hexanyl]methanol
• CAS: 1181843-99-1
• 化学式: C₁₁H₂₀O₅
• 分子量: 232.277
• InChiKey: AFZRPQMFBXYSMV-BBBLOLIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  79.2
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4β-(Hydroxymethyl)-thujan-3-one 在 D(+)-10-樟脑磺酸 、 双氧水 作用下， 以 乙醚 、 水 为溶剂， 反应 16.0h， 以35%的产率得到3,3-dihydroperoxy4-(hydroxymethyl)-β-thujane
  参考文献：
  名称：

  Enantioselective epoxidation of tertiary allylic alcohols by chiral dihydroperoxides

  摘要：

  gem-Dihydroperoxides were successfully used for the enantioselective epoxidation of tertiary and primary allylic alcohols. Epoxides derived from tertiary alcohols were obtained in yields up to 71% with ee's up to 52%. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.01.032
• 作为试剂：
  描述：

  (E)-3-(4-氯苯基)-2-丙烯-1-醇 在 titanium(IV) isopropylate 、 3,3-dihydroperoxy4-(hydroxymethyl)-β-thujane 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 以57%的产率得到
  参考文献：
  名称：

  Enantioselective epoxidation of tertiary allylic alcohols by chiral dihydroperoxides

  摘要：

  gem-Dihydroperoxides were successfully used for the enantioselective epoxidation of tertiary and primary allylic alcohols. Epoxides derived from tertiary alcohols were obtained in yields up to 71% with ee's up to 52%. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.01.032

文献信息

• Enantioselective epoxidation of 2-substituted 1,4-naphthoquinones using gem-dihydroperoxides
  作者：Alexander Bunge、Hans-Jürgen Hamann、Eve McCalmont、Jürgen Liebscher

  DOI：10.1016/j.tetlet.2009.05.096

  日期：2009.8

  New gem-dihydroperoxides were successfully used for DBU-promoted enantioselective epoxidation of 2-substituted 1,4-naphtlloquinones. The corresponding 1,4-naphthoquinone epoxides were obtained in yields up to 97% and ee's up to 82%. (C) 2009 Elsevier Ltd. All rights reserved.
• Enantioselective epoxidation of tertiary allylic alcohols by chiral dihydroperoxides
  作者：Alexander Bunge、Hans-Jürgen Hamann、Dennis Dietz、Jürgen Liebscher

  DOI：10.1016/j.tet.2013.01.032

  日期：2013.3

  gem-Dihydroperoxides were successfully used for the enantioselective epoxidation of tertiary and primary allylic alcohols. Epoxides derived from tertiary alcohols were obtained in yields up to 71% with ee's up to 52%. (c) 2013 Elsevier Ltd. All rights reserved.