(1R*,3S*,5R*,7S*)-6,6-dimethoxy-4,8-dioxatricyclo[5.1.0.0(3,5)]octan-2-one | 84036-81-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: (1R*,3S*,5R*,7S*)-6,6-dimethoxy-4,8-dioxatricyclo[5.1.0.0(3,5)]octan-2-one
• 英文别名: (1S,3R,5S,7R)-6,6-dimethoxy-4,8-dioxatricyclo[5.1.0.03,5]octan-2-one
• CAS: 84036-81-7
• 化学式: C₈H₁₀O₅
• 分子量: 186.164
• InChiKey: LFUJVYPQPTUEFZ-UMRXKNAASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  60.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1R*,3S*,5R*,7S*)-6,6-dimethoxy-4,8-dioxatricyclo[5.1.0.0(3,5)]octan-2-one 、 烯丙基三氟硼酸钾 在 indium 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 8.0h， 生成 (1R*,2R*,3S*,5R*,7S*)-6,6-dimethoxy-2-(prop-2-en-1-yl)-4,8-dioxatricyclo[5.1.0.0(3,5)]octan-2-ol 、 (1R*,2S*,3S*,5R*,7S*)-6,6-dimethoxy-2-(prop-2-en-1-yl)-4,8-dioxatricyclo[5.1.0.0(3,5)]octan-2-ol
  参考文献：
  名称：

  Indium-Promoted Chemo- and Diastereoselective Allylation of α,β-Epoxy Ketones with Potassium Allyltrifluoroborate

  摘要：

  A practical method for the chemo- and diastereoselective allylation of alpha,beta-epoxy ketones has been developed by using the convenient air and moisture stable reagent potassium allyltrifluoroborate. Indium metal was found to promote addition in stoichiometric or catalytic amounts, to afford alpha,beta-epoxyhomoallylic tertiary alcohols in high yields and diastereoselectivities, without competing ring-scission of the epoxide.

  DOI：

  10.1021/ol1023757
• 作为产物：
  描述：

  (1S,3R,5S,7R)-6,6-dimethoxy-4,8-dioxatricyclo[5.1.0.03,5]octane-2,2-diol 以99%的产率得到
  参考文献：
  名称：

  KELLER, R.

  摘要：

  DOI：

文献信息

• Organometallic additions to protected quinone bis-epoxides and quinone monoacetals: synthesis of the aranorosin nucleus
  作者：Alexander McKillop、Richard J. K. Taylor、Robert J. Watson、Norman Lewis

  DOI：10.1039/c39920001589

  日期：——

  The addition reactions of organometallic reagents to monoprotected quinone bis-epoxides 7 and quinone monoacetals 5 provide a route to the highly oxygenated cyclohexanols 2 and 3; the application of this methodology to the preparation of the aranorosin analogue 4 is described.

  有机金属试剂与单保护醌双环氧化物 7 和醌单乙醛 5 的加成反应提供了一种获得高含氧环己醇 2 和 3 的途径；本文介绍了应用这种方法制备阿糖胞苷类似物 4 的情况。
• Acetal and ketal deprotection using montmorillonite K10: The first synthesis of syn-4,8-dioxatricyclo[5.1.0.03,5]-2,6-octanedione
  作者：Elisabeth C.L Gautier、Andrew E Graham、Alexander McKillop、Stephen P Standen、Richard J.K Taylor

  DOI：10.1016/s0040-4039(97)00226-8

  日期：1997.3

  Montmorillonite K10 in dichloromethane at room temperature conveniently and efficiently converts acetals and ketals into the corresponding carbonyl compounds. The title dione (diepoxy-1-4-cyclohexanedione) has been prepared for the first time using this procedure. (C) 1997 Elsevier Science Ltd.