(3S,4R)-3,4,8-trihydroxy-1-tetralone | 149341-67-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (3S,4R)-3,4,8-trihydroxy-1-tetralone
• 英文别名: (3S,4R)-3,4,8-trihydroxytetralone；cis-4-hydroxy-6-deoxyscytalone；3,4-dihydro-3,4,8-trihydroxy-1(2H)-naphthalenone；(3S,4R)-3,4,8-trihydroxy-3,4-dihydro-2H-naphthalen-1-one
• CAS: 149341-67-3
• 化学式: C₁₀H₁₀O₄
• 分子量: 194.187
• InChiKey: HPIFRXWPEZBFHJ-WCBMZHEXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (-)-2,5-diacetoxy-1-hydroxy-1,2,3,4-tetrahydronaphthalene 在 吡啶 、 乙酸酐 、 chromium(VI) oxide 、 甲醇 、 potassium carbonate 作用下， 生成 (3S,4R)-3,4,8-trihydroxy-1-tetralone
  参考文献：
  名称：

  Lipase-catalyzed resolution of 5-acetoxy-1,2-dihydroxy-1,2,3,4-tetrahydronaphthalene. Application to the synthesis of (+)-(3R,4S)-cis-4-hydroxy-6-deoxyscytalone, a metabolite isolated from Colletotrichum acutatum

  摘要：

  **(+)-顺式-4-羟基福烯-6-脱氧赛肽酮**，一种由Colletotrichum sp.生物合成的天然产物，已被成功制备，其绝对构型经确认为3R,4S。关键步骤在于对易从商业1,2,3,4-四氢萘-1,5-二醇获取的顺式二醇进行动力学消旋拆分。同时测试了四种脂肪酶和不同反应条件，以获得最优产率和对映体过量。绝对构型的确证通过核磁共振（NMR）完成，采用了单一步骤衍生化低温方法，并以MPA作为辅助试剂。 （C）2009 Elsevier Ltd. 保留所有权利。

  DOI：

  10.1016/j.tet.2009.02.054

文献信息

• Asymmetric Synthesis of Natural <i>cis</i>-Dihydroarenediols Using Tetrahydroxynaphthalene Reductase and Its Biosynthetic Implications
  作者：Nirmal Saha、Michael Müller、Syed Masood Husain

  DOI：10.1021/acs.orglett.9b00500

  日期：2019.4.5

  Asymmetric reduction of hydroxynaphthoquinones to secondary metabolites, (3S,4R)-3,4,8- and (2S,4R)-2,4,8-trihydroxy-1-tetralone, a putative biosynthetic diketo intermediate and a probable natural analogue, (3S,4R)-7-acetyl-3,4,8-trihydroxy-6-methyl-3,4-dihydronaphthalene-1(2H)-one, using NADPH-dependent tetrahydroxynaphthalene reductase (T4HNR) of Magnaporthe grisea is described. This work implies

  羟基萘醌不对称还原为次级代谢产物（3 S，4 R）-3,4,8-和（2 S，4 R）-2,4,8-三羟基-1-四氢萘酮，一种假定的生物合成二酮中间体和可能天然类似物，（3小号，4 - [R）-7-乙酰基3,4,8-三羟基-6-甲基-3,4-二氢萘-1（2 ħ） -酮，使用NADPH依赖性羟基萘还原酶（T描述了稻瘟病菌（Magnaporthe grisea）的4 HNR）。这项工作暗示通过减少含羟基萘醌支架的底物，在其他二氢芳烃的（生物）合成过程中，T 4 HNR或相关酶的参与。
• One-step enantioselective synthesis of (4S)-isosclerone through biotranformation of juglone by an endophytic fungus
  作者：Soizic Prado、Didier Buisson、Idrissa Ndoye、Marine Vallet、Bastien Nay

  DOI：10.1016/j.tetlet.2012.12.038

  日期：2013.3

  We describe here a direct access to (4S)-isosclerone (+)-1, an important structural component of several natural products featuring a spirobisnaphthalene ring system. Starting with the commercially available 5-hydroxy-1,4-naphthalenedione (juglone), biotransformation by the isosclerone-producing endophytic fungus Paraconiothyrium variabile is described. The absolute configuration of (+)-1 was determined unambiguously using circular dichroism and by measurement of the optical rotation. Moreover, the bio-transformations of other naphthalene derivatives were undertaken and led to the corresponding (4S)-hydroxy-l-tetralone. At last, this work brings some insights on the biosynthesis of natural tetralones. (C) 2012 Elsevier Ltd. All rights reserved.
• Lipase-catalyzed resolution of 5-acetoxy-1,2-dihydroxy-1,2,3,4-tetrahydronaphthalene. Application to the synthesis of (+)-(3R,4S)-cis-4-hydroxy-6-deoxyscytalone, a metabolite isolated from Colletotrichum acutatum
  作者：Daniel Jiménez-Teja、Mourad Daoubi、Isidro G. Collado、Rosario Hernández-Galán

  DOI：10.1016/j.tet.2009.02.054

  日期：2009.4

  (+)-cis-4-Hyd Foxy-6-deoxyscytalone, a natural product bio-synthesized by Colletotrichum sp., has been prepared and its absolute configuration confirmed as 3R,4S, the key step being a kinetic racemic resolution of a cis-diol easily obtained from commercial 1,2,3.4-tetrahydronaphthalen-1,5-diol. Four lip ases and different reaction conditions were tested in order to obtain the best yield and enantiomeric excess. Confirmation of absolute configuration was made by NMR using a single-derivatization low-temperature Procedure and MPA as the auxiliary reagent. (C) 2009 Elsevier Ltd. All rights reserved.

  **(+)-顺式-4-羟基福烯-6-脱氧赛肽酮**，一种由Colletotrichum sp.生物合成的天然产物，已被成功制备，其绝对构型经确认为3R,4S。关键步骤在于对易从商业1,2,3,4-四氢萘-1,5-二醇获取的顺式二醇进行动力学消旋拆分。同时测试了四种脂肪酶和不同反应条件，以获得最优产率和对映体过量。绝对构型的确证通过核磁共振（NMR）完成，采用了单一步骤衍生化低温方法，并以MPA作为辅助试剂。 （C）2009 Elsevier Ltd. 保留所有权利。