1-(2,4-二羟基-3,5-二甲基苯基)-乙酮 | 577-45-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-(2,4-二羟基-3,5-二甲基苯基)-乙酮
• 英文名称: clavatol
• 英文别名: 1-(2,4-Dihydroxy-3,5-dimethylphenyl)ethanone
• CAS: 577-45-7
• 化学式: C₁₀H₁₂O₃
• 分子量: 180.203
• InChiKey: AMZNYVFIWCPUAY-UHFFFAOYSA-N

物化性质

• 熔点：
  184–186°C

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• 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：

  1-(2,4-二羟基-3,5-二甲基苯基)-乙酮 在 alpha-酮戊二酸 、 claD 、 氧气 、 iron(II) sulfate 、 sodium ascorbate 作用下， 以 aq. buffer 为溶剂， 反应 3.0h， 以65%的产率得到hydroxyclavatol
  参考文献：
  名称：

  化学酶促邻醌甲基化物形成

  摘要：

  在生理条件下生成反应性中间体和拦截这些转瞬即逝的物种是大自然用来构建分子复杂性的常用策略。然而，使用经典合成技术在温和条件下选择性形成这些物种是一个突出的挑战。在这里，我们展示了生物催化在温和的水性条件下产生具有精确化学选择性的邻醌甲基化物中间体的效用。具体而言，α-酮戊二酸依赖性非血红素铁酶 CitB 和 ClaD 用于选择性修饰邻甲酚底物的苄基 CH 键。在该转化中，苄基 CH 键的生物催化羟基化产生苄醇产物，在水性反应条件下，该产物与相应的邻醌甲基化物处于平衡状态。亲核试剂或亲双烯试剂对邻醌甲基化物的拦截允许在制备规模的化学酶级联中将苄型 CH 键一锅转化为 CC、CN、CO 和 CS 键。该平台的化学选择性和温和性质在这里通过肽的选择性修饰和色满天然产物 (-)-xyloketal D 的化学酶促合成展示。

  DOI：

  10.1021/jacs.9b10474
• 作为产物：
  描述：

  2,4-二羟基苯-1,3-二甲醛 在 盐酸 、 palladium on activated charcoal 、 乙醚 、 溶剂黄146 、 zinc(II) chloride 作用下， 生成 1-(2,4-二羟基-3,5-二甲基苯基)-乙酮
  参考文献：
  名称：

  Effects of Bleomycin on Liver Antioxidant Enzymes and the Electron Transport System From Ad Libitum-Fed and Dietary-Restricted Female and Male Fischer 344 Rats

  摘要：

  Dietary restriction (DR) is the only known intervention that delays aging and age-related diseases. Mechanisms proposed to explain this DR effect include a decline in free radical production and an increase in free radical detoxification. In the present study the effect of bleomycin (BLM) as a reactive oxygen species-generating antitumor drug has been evaluated on antioxidant enzymes and the electron transport system in different cellular fractions of liver in female and male Fischer 344 rats. Animals were fed ad libitum (AL) or 60% of the AL intake (DR) and were given a single intraperitoneal injection of 2.5, 5, or 10 mg BLM/kg body wt. After four weeks, BLM significantly increased glutathione peroxidase and lactate dehydrogenase activities in liver cytosol of female AL rats and increased activity even more in male rats. Similar changes were also noted for glutathione reductase and glucose 6-phosphate dehydrogenase activities in BLM-treated AL rats. In liver mitochondria, glutathione peroxidase was increased in female and male AL rats but was increased more in female rats. Drug treatment had no significant effect on these enzyme activities in cytosolic or mitochondrial fractions of DR animals. Profound effects of BLM were noted in activities of complexes I, III, and IV of the electron transport system in AL and DR female and male rats; however, complex II demonstrated no significant diet or treatment effect. Induced antioxidant enzyme activities in BLM-treated AL rats may be a response to excessive free radical generation due to BLM metabolism in AL animals that is mitigated by DR. Furthermore, dysfunction of the electron transport system might suggest its role in a secondary generation of free radicals during BLM metabolism contributing to its toxicity.

  DOI：

  10.1207/s15327914nc3601_7

文献信息

• Biomimetic Total Synthesis of Bisorbicillinol, Bisorbibutenolide, Trichodimerol, and Designed Analogues of the Bisorbicillinoids
  作者：K. C. Nicolaou、Georgios Vassilikogiannakis、Klaus B. Simonsen、Phil S. Baran、Yong-Li Zhong、Veroniki P. Vidali、Emmanuel N. Pitsinos、Elias A. Couladouros

  DOI：10.1021/ja9942843

  日期：2000.4.1

  biological activity and are associated with fascinating hypotheses for their biosynthesis. A full account of our biomimetic explorations toward the bisorbicillinoids including the total syntheses of bisorbicillinol (1), bisorbibutenolide (2), and trichodimerol (4) from sorbicillin (3) is disclosed. Utilizing the novel dimerization reactions discovered and fine-tuned en route to 1 and 4, several analogues of

  Bisorbicillinoids 是一类不断增长的新型天然产物，具有独特的生物活性，并与它们生物合成的迷人假设有关。公开了我们对双山梨醇类化合物的仿生探索的完整描述，包括双山梨醇 (1)、双山梨醇内酯 (2) 和来自山梨西林 (3) 的三聚二聚体 (4) 的全合成。利用在 1 和 4 过程中发现和微调的新型二聚反应，合成了这些天然产物的几种类似物。此外，还报告了对这些新型环加成反应的范围和许多意外产物的分离及其形成机制的研究。这些发现增加了我们对 o-quinols 和相关芳香系统的大部分未探索化学的了解。
• Total Synthesis and Stereochemical Assignment of (±)-Sorbiterrin A
  作者：Chao Qi、Tian Qin、Daisuke Suzuki、John A. Porco

  DOI：10.1021/ja500854q

  日期：2014.3.5

  sorbiterrin A has been developed employing consecutive Michael additions of a 4-hydroxypyrone to a sorbicillinol derivative and silver nanoparticle-mediated bridged aldol/dehydration to construct the [3.3.1] ring system. The relative stereochemistry of sorbiterrin A was unambiguously confirmed by X-ray crystallographic analysis.

  已经开发了一种针对山梨糖醇酐 A 的简明仿生方法，该方法采用连续迈克尔加成将 4-羟基吡喃酮添加到山梨醇衍生物和银纳米颗粒介导的桥接羟醛/脱水来构建 [3.3.1] 环系统。X 射线晶体学分析明确证实了山梨糖醇 A 的相对立体化学。
• Biocatalytic site- and enantioselective oxidative dearomatization of phenols
  作者：Summer A. Baker Dockrey、April L. Lukowski、Marc R. Becker、Alison R. H. Narayan

  DOI：10.1038/nchem.2879

  日期：2018.2

  Biocatalytic site- and enantioselective oxidative dearomatization of phenols Biocatalytic site- and enantioselective oxidative dearomatization of phenols, Published online: 13 November 2017; doi:10.1038/nchem.2879NatureArticleSnippet(type=short-summary, markup= Within natural product biosynthetic pathways, nature has evolved highly selective catalysts capable of complexity generating reactions. Leveraging

  酚类的生物催化位点和对映选择性氧化脱芳构化 苯酚的生物催化位点和对映选择性氧化脱芳构化，在线发布：2017 年 11 月 13 日；doi：10.1038/nchem.2879NatureArticleSnippet（类型=简短摘要，标记= 在天然产物生物合成途径中，大自然已经进化出能够产生复杂反应的高选择性催化剂。利用这些工具，一套具有互补位点和立体选择性的催化剂已应用于酚类化合物的氧化脱芳构化，使酚类一锅法转化为各种天然产物。, isJats=true)
• Synthesis of three natural 1,3-diarylpropanes: Two revised structures
  作者：Anselmo A. Morais、Raimundo Braz Fo、Silas V. Fraiz

  DOI：10.1016/0031-9422(89)85046-0

  日期：——

  5′-dimethylphenyl)-3-(2″-hydroxy-4″,5″-methylenedioxyphenyl)-Propane, isolated from Iryanthera coriacea and I. laevis, 1-(2′-hydroxy-4′-methoxy-5′-methylphenyl)-3-(2″-hydroxy-4″,5″-methylene-dioxyphenyl)-propane, isolated from I. laevis, and 1-(2′-hydroxy-4′-methoxyphenyl)-3-(3″-hydroxy-4″-methoxyphenyl)-propane, isolated from Virola multinervia, were synthesized by processes which involved catalytic hydrogenation

  摘要 1-(2',4'-dihydroxy-3',5'-二甲基苯基)-3-(2"-hydroxy-4",5"-methylenedioxyphenyl)-Propane，从 Iryanthera coriacea 和 I. laevis 中分离出来，1 -(2'-羟基-4'-甲氧基-5'-甲基苯基)-3-(2"-羟基-4",5"-亚甲基-二氧苯基)-丙烷，从 I. laevis 中分离，和 1-(2 '-羟基-4'-甲氧基苯基)-3-(3″-羟基-4″-甲氧基苯基)-丙烷，从多神经病毒中分离，通过涉及适当查耳酮的催化氢化和二氢查耳酮的克莱门森还原的方法合成。仅修订了从 V. multinervia 和 I. laevis 中分离出来的 1,3-二芳基丙烷的结构。
• Mold Metabolites. III. The Structure of Citrinin
  作者：Donald J. Cram

  DOI：10.1021/ja01192a078

  日期：1948.12