(1R,2R,3S,4S)-4-acetoxy-8-benzyloxy-2,3-epoxy-1,2,3,4-tetrahydronaphthalen-1-ol | 794575-12-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (1R,2R,3S,4S)-4-acetoxy-8-benzyloxy-2,3-epoxy-1,2,3,4-tetrahydronaphthalen-1-ol
• 英文别名: [(1aR,2R,7S,7aS)-2-hydroxy-3-phenylmethoxy-1a,2,7,7a-tetrahydronaphtho[2,3-b]oxiren-7-yl] acetate
• CAS: 794575-12-5
• 化学式: C₁₉H₁₈O₅
• 分子量: 326.349
• InChiKey: DTRMRBYEUQQLEZ-HCXYKTFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  68.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1R,2R,3S,4S)-4-acetoxy-8-benzyloxy-2,3-epoxy-1,2,3,4-tetrahydronaphthalen-1-ol 在 咪唑 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 25.0h， 生成 (1S,2S,3S,4R)-8-benzyloxy-4-(tert-butyldimethylsilyloxy)-2,3-epoxy-1,2,3,4-tetrahydronaphthalen-1-ol
  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：

  8-benzyloxy-2,3-epoxy-1,2α,3α,4-tetrahydronaphthalene-1,4-dione 在 Burholderia cepacia lipase 、 potassium tri-sec-butyl-borohydride 作用下， 以 四氢呋喃 为溶剂， 反应 19.0h， 生成 (1R,2R,3S,4S)-4-acetoxy-8-benzyloxy-2,3-epoxy-1,2,3,4-tetrahydronaphthalen-1-ol
  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