2,3-epoxy-1α,2α,3α,4α-tetrahydronaphthalene-1,4-diol | 25129-70-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 2,3-epoxy-1α,2α,3α,4α-tetrahydronaphthalene-1,4-diol
• 英文别名: 2,3r-Epoxy-1,2,3,4-tetrahydro-naphthalin-1c,4c-diol；(1aR,2R,7S,7aS)-1a,2,7,7a-tetrahydronaphtho[2,3-b]oxirene-2,7-diol
• CAS: 25129-70-8
• 化学式: C₁₀H₁₀O₃
• 分子量: 178.188
• InChiKey: UBZIRRGOXVDJQB-YNFQOJQRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  53
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,3-epoxy-1α,2α,3α,4α-tetrahydronaphthalene-1,4-diol 在 咪唑 、 Burholderia cepacia lipase 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 (1S,2S,3S,4R)-1-acetoxy-4-(tert-butyldimethylsilyloxy)-2,3-epoxy-1,2,3,4-tetrahydronaphthalene
  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：

  1,4-萘醌 在 sodium tetrahydroborate 、 双氧水 、 potassium carbonate 作用下， 以 甲醇 、 水 、 丙酮 为溶剂， 反应 5.0h， 生成 2,3-epoxy-1α,2α,3α,4α-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

文献信息

• Ru-Catalyzed Asymmetric Hydrogenative/Transfer Hydrogenative Desymmetrization of Meso-Epoxy Diketones
  作者：Yuping Hong、Jianzhong Chen、Zhenfeng Zhang、Yangang Liu、Wanbin Zhang

  DOI：10.1021/acs.orglett.6b01073

  日期：2016.6.3

  Via a strategy of asymmetric reductive desymmetrization, chiral cis-epoxy naphthoquinols with multiple contiguous stereocenters and functional groups were synthesized with excellent enantioselectivities (96–99% ee) and diastereoselectivities (8/1–15/1). A combined asymmetric hydrogenation/transfer hydrogenation mechanism was proposed based on experimental results.

  通过不对称还原去对称化的策略，合成了具有多个连续立体中心和官能团的手性顺式-环氧萘醌，具有优异的对映选择性（96-99％ee）和非对映选择性（8 / 1-15 / 1）。根据实验结果，提出了一种不对称加氢/转移加氢的联合机理。