5,8-diallyloxy-1,4-naphthoquinone | 794575-15-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5,8-diallyloxy-1,4-naphthoquinone
• 英文别名: 5,8-Bis(prop-2-enoxy)naphthalene-1,4-dione
• CAS: 794575-15-8
• 化学式: C₁₆H₁₄O₄
• 分子量: 270.285
• InChiKey: BDOIQWAYRJBYQX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5,8-diallyloxy-1,4-naphthoquinone 在 sodium tetrahydroborate 、 双氧水 、 sodium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 0.5h， 生成 5,8-diallyloxy-2,3-epoxy-1β,2β,3β,4β-tetrahydronaphthalene-1,4-diol
  参考文献：
  名称：

  Enzymatic desymmetrization/resolution of epoxydiols derived from 1,4-naphthoquinone, 5-hydroxy-1,4-naphthoquinone and 5,8-dihydroxy-1,4-naphthoquinone

  摘要：

  The enzymatic desymmetrization/resolution of epoxydiols generated from the basic epoxidation and reduction of 1,4-naphthoquoinone, 5-hydroxy-1,4-naphthoquinone and 5,8-dihydroxy-1,4-naphthoquinone is described. 2,3-Epoxy-1(alpha),2(alpha),3(alpha),4(alpha)-tetrahydronaphthalene-1,4-diol and 5,8-diallyloxy-2,3-epoxy-1(alpha),2(alpha),3(alpha),4(alpha)-tetrahydronaphthalene-1,4-diol were desymmetrized in the presence of isopropenyl acetate using Burholderia cepacia lipase and Candida antartica lipase B, respectively. An enzymatic resolution of 8-benzyloxy-2,3-epoxy-1(alpha),2(alpha),3(alpha),4(alpha)-tetrahydronaphthalene-1,4-diol using B. cepacia lipase in isopropenyl acetate is also described. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.07.051
• 作为产物：
  描述：

  丙烯酰碘 、 萘茜 在 silver(l) oxide 作用下， 反应 28.0h， 以81%的产率得到5,8-diallyloxy-1,4-naphthoquinone
  参考文献：
  名称：

  Enzymatic desymmetrization/resolution of epoxydiols derived from 1,4-naphthoquinone, 5-hydroxy-1,4-naphthoquinone and 5,8-dihydroxy-1,4-naphthoquinone

  摘要：

  The enzymatic desymmetrization/resolution of epoxydiols generated from the basic epoxidation and reduction of 1,4-naphthoquoinone, 5-hydroxy-1,4-naphthoquinone and 5,8-dihydroxy-1,4-naphthoquinone is described. 2,3-Epoxy-1(alpha),2(alpha),3(alpha),4(alpha)-tetrahydronaphthalene-1,4-diol and 5,8-diallyloxy-2,3-epoxy-1(alpha),2(alpha),3(alpha),4(alpha)-tetrahydronaphthalene-1,4-diol were desymmetrized in the presence of isopropenyl acetate using Burholderia cepacia lipase and Candida antartica lipase B, respectively. An enzymatic resolution of 8-benzyloxy-2,3-epoxy-1(alpha),2(alpha),3(alpha),4(alpha)-tetrahydronaphthalene-1,4-diol using B. cepacia lipase in isopropenyl acetate is also described. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.07.051