(4R)-3,4-二氢-4,8-二羟基-1(2H)-萘酮 | 137494-04-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 中文名称: (4R)-3,4-二氢-4,8-二羟基-1(2H)-萘酮
• 英文名称: isosclerone
• 英文别名: regiolone；(4R)-4,8-dihydroxy-1-tetralone；(4R)-4,8-dihydroxy-3,4-dihydro-2H-naphthalen-1-one
• CAS: 137494-04-3
• 化学式: C₁₀H₁₀O₃
• 分子量: 178.188
• InChiKey: ZXYYTDCENDYKBR-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  13
• 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：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4R)-3,4-二氢-4,8-二羟基-1(2H)-萘酮 、 苯甲酰氯 在 吡啶 作用下， 反应 24.0h， 以0.3 mg的产率得到(4R)-4,8-dibenzyloxy-α-tetralone
  参考文献：
  名称：

  Studies on the Constituents of Juglans Species. I. Structural Determination of (4S)- and (4R)-4-Hydroxy-.ALPHA.-tetralone Derivatives from the Fruit of Juglans mandshurica MAXIM. var. sieboldiana MAKINO

  摘要：

  从胡桃（Juglans mandshurica MAXIM. var. sieboldiana MAKINO）果实中分离出四种对映体纯的α-四氢萘酮新化合物（4S）-和（4R）-5-羟基-4-甲氧基-α-四氢萘酮以及（4S）-和（4R）-5,8-二羟基-4-甲氧基-α-四氢萘酮，以及五种已知化合物（4S）-和（4R）-4,8-二羟基-α-四氢萘酮、（4S）-4,8-二羟基-5-甲氧基-α-四氢萘酮以及（4S）-和（4R）-4-羟基-α-四氢萘酮。它们的结构是根据光谱分析确定的。据我们所知，这是首次从胡桃属物种中分离出（4R）-4-羟基-α-四氢萘酮衍生物。

  DOI：

  10.1248/cpb.53.934
• 作为产物：
  描述：

  (R)-4-((3,4-dihydroxy-6-(hydroxymethyl)-5-methoxytetrahydro-2H-pyran-2-yl)oxy)-8-hydroxy-3,4-dihydronaphthalen-1(2H)-one 在 alpha-L-rhamnosidase 作用下， 以 aq. acetate buffer 为溶剂， 反应 12.0h， 生成 (4R)-3,4-二氢-4,8-二羟基-1(2H)-萘酮
  参考文献：
  名称：

  A new β-tetralonyl glucoside from the Santalum album derived endophytic fungus Colletotrichum sp. GDMU-1

  摘要：

  A new beta-tetralonyl glucoside, methylberchemiaside (1), along with five known compounds (2-6) were isolated from a fungus Colletotrichum sp. GDMU-1 derived from the leaves of Santalum album. Their structures were determined by detailed analysis of spectroscopic data. All compounds were tested for the inhibitory effects on the nitric oxide (NO) production in lipopolysaccharide (LPS)-treated RAW264.7 cells. Among them, compounds 4 and 5 showed moderate anti-inflammatory activity with IC50 value of 30.4 and 8.9 mu M, respectively.[GRAPHICS].

  DOI：

  10.1080/14786419.2018.1452003

文献信息

• Enantioselective Separation of 4,8-DHT and Phytotoxicity of the Enantiomers on Various Plant Species
  作者：Li Yang、Xiao-Yan Ma、Xiao Ruan、De-An Jiang、Cun-De Pan、Qiang Wang

  DOI：10.3390/molecules21040528

  日期：——

  As a candidate for bioherbicide, 4,8-dihydroxy-1-tetralone (4,8-DHT) was isolated from Caryospora callicarpa epicarp and its two enantiomers, S-(+)-isosclerone and R-(−)-regiolone, were separated by chiral high-performance liquid chromatography (HPLC) on a Chiralcel OD column with chiral stationary phase (CSP)-coated cellulose-tris(3,5-dimethylphenylcarbamate). Then, the phytotoxicity of 4,8-DHT and its enantiomers toward the seeds germination and seedling growth of the five tested plant species, including lettuce (Latuca sativa), radish (Raphanus sativus), cucumber (Cucumis sativus), onion (Allium cepa), and wheat (Triticum aestivum), were investigated and the results indicated a hormesis at low concentration of 4,8-DHT and its enantiomers, but a retardant effect at high concentration. Between the two enantiomers of 4,8-DHT, the S-(+)-isosclerone was more toxic to seeds germination and seedling growth of the five tested plant species than the R-(−)-regiolone, and also the phytotoxicity of S-(+)-isosclerone varied with different plants. For example, S-(+)-isosclerone was the most active to seedling growth of lettuce, indicating that S-(+)-isosclerone had specific effects on different organisms. Thus, all of the chirality and concentration of 4,8-DHT, as well as the affected plant species, need to be taken into consideration in the development and utilization of 4,8-DHT.

  作为生物除草剂的候选物质，从苦楝树外皮中分离出4,8-二羟基-1-四氢萘酮（4,8-DHT），并通过手性高效液相色谱（HPLC）在Chiralcel OD柱上分离出其两个对映体S-(+)-异石竹酮和R-(-)-雷吉酮。该柱上涂有手性固定相（CSP）的纤维素-三（3,5-二甲基苯基氨基甲酸酯）。然后，研究了4,8-DHT及其对映体对五种测试植物（包括莴苣（Latuca sativa）、萝卜（Raphanus sativus）、黄瓜（Cucumis sativus）、洋葱（Allium cepa）和小麦（Triticum aestivum））的种子发芽和幼苗生长的植物毒性，结果表明，低浓度的4,8-DHT及其对映体具有激素效应，而高浓度则具有抑制作用。在4,8-DHT的两个对映体中，S-(+)-异石竹酮对五种测试植物的种子发芽和幼苗生长的毒性比R-(-)-雷吉酮更强，而且S-(+)-异石竹酮的植物毒性也因植物而异。例如，S-(+)-异石竹酮对莴��
• Asymmetric synthesis of (+)-teratosphaerone B, its non-natural analogue and (+)-xylarenone using an ene- and naphthol reductase cascade
  作者：Tanaya Manna、Arijit De、Khondekar Nurjamal、Syed Masood Husain

  DOI：10.1039/d2ob01262f

  日期：——

  a one-pot bienzymatic cascade containing an ene and a naphthol reductase is developed. It is applied for the synthesis of (+)-(3R,4R)-teratosphaerone B, its non-natural regioisomer in both cis- and trans-forms and (+)-xylarenone by the reduction of chemically synthesized naphthoquinone precursors in high yields (76–92%) and excellent ee (>99%). This work implies similar biosynthetic steps in the formation

  在此，开发了包含烯和萘酚还原酶的一锅双酶级联。它用于通过还原化学合成的萘醌前体来合成 (+)-(3 R ,4 R )-teratosphaerone B、其顺式和反式的非天然区域异构体和 (+)-xylarenone高产量 (76–92%) 和出色的 ee (>99%)。这项工作意味着在合成天然产物的形成中具有类似的生物合成步骤。