1-hydroxy-2-naphthyl(4-Me-styryl)keton | 57822-51-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 1-hydroxy-2-naphthyl(4-Me-styryl)keton
• 英文别名: 2-(p-Methylcinnamoyl)-1-naphthol；1-(1-hydroxynaphthalen-2-yl)-3-(4-methylphenyl)prop-2-en-1-one
• CAS: 57822-51-2
• 化学式: C₂₀H₁₆O₂
• 分子量: 288.346
• InChiKey: LPRBBVARHHTUBA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-hydroxy-2-naphthyl(4-Me-styryl)keton 在 碘 作用下， 以 二甲基亚砜 为溶剂， 反应 4.0h， 生成 2-p-tolyl-4H-benzo[h]chromen-4-one
  参考文献：
  名称：

  α-和β-naphthoflavones的作为单加氧酶抑制剂的应用蓝色犁头霉KCH 93，Syncephalastrum蔓KCH 105和球毛壳菌。KCh 6651转化17α-甲基睾丸酮

  摘要：

  在这项工作中，芥蓝KCh 93，Syncephalastrum racemosum KCh 105和Chaetomium sp有效地羟基化了17α-甲基睾丸激素。KCH 6651. A.犁头KCH 93得到6β-，12β-，7α-，11α-，15α羟基衍生物与分别为44％，29％，6％，5％和9分％的收率。小号。总消旋体KCh 105提供7α-，15α-和11α-羟基衍生物，产率分别为45％，19％和17％。毛毛虫sp。KCh 6651提供15α-，11α-，7α-，6β-，9α-，14α-羟基和6β，14α-二羟基衍生物，产率分别为31％，20％，16％，7％，5％，7％和4 ％， 分别。确定了14α-羟基和6β，14α-二羟基衍生物为新化合物。测试了培养基中氮和碳的各种来源对生物转化的影响，但是没有影响底物转化的程度或形成的产物的组成。添加α-或β-萘黄酮抑制了17α-甲基睾丸酮的羟化作用，但没有改变所得产物的百分比组成。

  DOI：

  10.1016/j.bioorg.2018.03.021
• 作为产物：
  描述：

  2-乙酰基-1-萘酚 、 对甲基苯甲醛 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 生成 1-hydroxy-2-naphthyl(4-Me-styryl)keton
  参考文献：
  名称：

  Fungal metabolism of naphthoflavones

  摘要：

  Naphthoflavones (benzoflavones) are synthetic flavonoids commonly used in drug metabolism studies as selective activators or inhibitors of cytochrome P-450 enzymes. Nowadays they are also used as a component of food supplements for body builders. There is no data regarding naphthoflavone microbial metabolism. In the present studies sixty-three fungal strains have been screened for their ability to transform alpha-naphthoflavone (7,8-benzoflavone) or beta-naphthoflavone (5,6-benzoflavone). Five strains belonging to the genera Penicillium, Cladosporium, Aspergillus and Verticillium transformed alpha-naphthoflavone and beta-naphthoflavone to the corresponding 4'-hydroxy derivatives. These selected fungi have been used in a further study on biotransformation of naphthoflavones with a differently substituted B-ring. Only 4'-methoxy derivatives have been transformed to the related 4'-hydroxy products. Selected strains are good biocatalysts to obtain 4'-hydroxy naphthoflavones in the one step reaction. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2015.04.007

文献信息

• Silica-Supported Silver as a Green and Sustainable Catalyst for the [3+2]-Cycloaddition Reaction of Azomethine Ylides with 2′-Hydroxychalcone Derivatives
  作者：Suchithra Madhavan、Sentaro Okamoto

  DOI：10.1002/cctc.201702035

  日期：2018.5.9

  A reusable heterogeneous silver nanoparticle catalyst supported on silica was used for the [3+2]‐cycloaddition reaction of azomethine ylides with 2′‐hydroxychalcone derivatives. The green and sustainable catalytic protocol afforded highly functionalized pyrrolidines, indolizidines, and pyrrolizidines in good yields with high regio‐ and diastereoselectivities.

  负载在二氧化硅上的可重复使用的异质银纳米颗粒催化剂用于偶氮甲亚胺与2'-羟基查耳酮衍生物的[3 + 2]-环加成反应。绿色和可持续的催化方案以高收率和高区域选择性和非对映选择性提供了高度官能化的吡咯烷，吲哚并咪唑和吡咯烷。
• Rajendar Reddy, Kamreddy; Mogilaiah, Kaleru; Sreenivasulu, Bathula, Collection of Czechoslovak Chemical Communications, 1988, vol. 53, # 3, p. 643 - 645
  作者：Rajendar Reddy, Kamreddy、Mogilaiah, Kaleru、Sreenivasulu, Bathula

  DOI：——

  日期：——
• Natarajan, C.; Tharmaraj, P., Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical
  作者：Natarajan, C.、Tharmaraj, P.

  DOI：——

  日期：——
• Fungal metabolism of naphthoflavones
  作者：Jarosław Popłoński、Sandra Sordon、Tomasz Tronina、Agnieszka Bartmańska、Ewa Huszcza

  DOI：10.1016/j.molcatb.2015.04.007

  日期：2015.7

  Naphthoflavones (benzoflavones) are synthetic flavonoids commonly used in drug metabolism studies as selective activators or inhibitors of cytochrome P-450 enzymes. Nowadays they are also used as a component of food supplements for body builders. There is no data regarding naphthoflavone microbial metabolism. In the present studies sixty-three fungal strains have been screened for their ability to transform alpha-naphthoflavone (7,8-benzoflavone) or beta-naphthoflavone (5,6-benzoflavone). Five strains belonging to the genera Penicillium, Cladosporium, Aspergillus and Verticillium transformed alpha-naphthoflavone and beta-naphthoflavone to the corresponding 4'-hydroxy derivatives. These selected fungi have been used in a further study on biotransformation of naphthoflavones with a differently substituted B-ring. Only 4'-methoxy derivatives have been transformed to the related 4'-hydroxy products. Selected strains are good biocatalysts to obtain 4'-hydroxy naphthoflavones in the one step reaction. (C) 2015 Elsevier B.V. All rights reserved.
• Application of α- and β-naphthoflavones as monooxygenase inhibitors of Absidia coerulea KCh 93, Syncephalastrum racemosum KCh 105 and Chaetomium sp. KCh 6651 in transformation of 17α-methyltestosterone
  作者：Tomasz Janeczko、Jarosław Popłoński、Ewa Kozłowska、Monika Dymarska、Ewa Huszcza、Edyta Kostrzewa-Susłow

  DOI：10.1016/j.bioorg.2018.03.021

  日期：2018.8

  and 9% yields, respectively. S. racemosum KCh 105 afforded 7α-, 15α- and 11α-hydroxy derivatives with yields of 45%, 19% and 17%, respectively. Chaetomium sp. KCh 6651 afforded 15α-, 11α-, 7α-, 6β-, 9α-, 14α-hydroxy and 6β,14α-dihydroxy derivatives with yields of 31%, 20%, 16%, 7%, 5%, 7% and 4%, respectively. 14α-Hydroxy and 6β,14α-dihydroxy derivatives were determined as new compounds. Effect of various

  在这项工作中，芥蓝KCh 93，Syncephalastrum racemosum KCh 105和Chaetomium sp有效地羟基化了17α-甲基睾丸激素。KCH 6651. A.犁头KCH 93得到6β-，12β-，7α-，11α-，15α羟基衍生物与分别为44％，29％，6％，5％和9分％的收率。小号。总消旋体KCh 105提供7α-，15α-和11α-羟基衍生物，产率分别为45％，19％和17％。毛毛虫sp。KCh 6651提供15α-，11α-，7α-，6β-，9α-，14α-羟基和6β，14α-二羟基衍生物，产率分别为31％，20％，16％，7％，5％，7％和4 ％， 分别。确定了14α-羟基和6β，14α-二羟基衍生物为新化合物。测试了培养基中氮和碳的各种来源对生物转化的影响，但是没有影响底物转化的程度或形成的产物的组成。添加α-或β-萘黄酮抑制了17α-甲基睾丸酮的羟化作用，但没有改变所得产物的百分比组成。