2-甲酰基-1,4-萘醌 | 76916-86-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 2-甲酰基-1,4-萘醌
• 英文名称: 2-formyl-1,4-naphthoquinone
• 英文别名: 1,4-Dioxo-1,4-dihydronaphthalene-2-carbaldehyde；1,4-dioxonaphthalene-2-carbaldehyde
• CAS: 76916-86-4
• 化学式: C₁₁H₆O₃
• 分子量: 186.167
• InChiKey: PKZDWACKQCQRSJ-UHFFFAOYSA-N

物化性质

• 沸点：
  359.4±42.0 °C(Predicted)
• 密度：
  1.464±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  51.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-甲酰基-1,4-萘醌 在 盐酸 、 air 、 silica gel 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 乙酸乙酯 为溶剂， 反应 3.25h， 生成 ethyl 4,9-dioxo-4,9-dihydronaphtho[2,3-b]thiophene-2-carboxylate
  参考文献：
  名称：

  An Improved Method for the Preparation of 4,7-Dioxo-4,7-dihydrobenzo[b]thiophene-2-carboxylates from 2-Acyl-1,4-benzoquinones and Mercaptoacetates

  摘要：

  4,7-Dioxo-4,7-dihydrobenzo[b]thiophene-2-carboxylates (4) have been synthesized in a one-pot procedure from 2-acyl-1,4-benzoquinones (1) and mercaptoacetates (2) by using 1-trimethylsilylimidazole as a protective reagent as well as a base. Thus, reaction of 1 with 2 in THF at room temperature was followed by treatment with excess of 1-trimethylsilylimidazole at 80 degreesC. Then the cooled mixture was hydrolyzed with hydrochloric acid and oxidized with cerium(IV) ammonium nitrate (CAN) to give the expected thiophenequinone derivatives (4). 4,9-Dioxo-4,9-dihydronaphtho[2,3-b]thiophene-2-carboxylates (7) were similarly prepared from 2-acyl-1,4-naphthoquinones (5) and mercaptoacetates, in general, by omitting the CAN oxidation procedure.

  DOI：

  10.3987/com-01-9358
• 作为产物：
  描述：

  1,4-二甲氧基萘-2-甲醛 在 ammonium cerium (IV) nitrate 作用下， 生成 2-甲酰基-1,4-萘醌
  参考文献：
  名称：

  使用吡啶基吡啶化学法短程合成功能化的五肽酮衍生物

  摘要：

  通过酰基甲基萘醌的环化反应，合成了在C-1具有乙缩醛功能的3-取代的五聚体衍生物。后者的萘醌是从2-二氧戊环基萘醌开始，通过化学计量的和催化的方法，采用各种吡啶鎓碘化物来制备的。

  DOI：

  10.1016/j.tet.2010.07.012

文献信息

• PDK4 INHIBITOR AND USE THEREOF
  申请人：THE KITASATO INSTITUE

  公开号：US20150344404A1

  公开（公告）日：2015-12-03

  The present invention to provide a novel pyruvate dehydrogenase kinase inhibitors. A pyruvate dehydrogenase kinase inhibitor comprising a compound represented by the general formula (I) as an active ingredient (wherein, ring A represents a 6-membered aromatic hydrocarbon ring optionally substituted with 2-4 substituents, R 1 and R 4 , which are the same or different, represent a hydrogen atom, a hydroxyl group, an optionally substituted C1-6 alkyl group, R 2 and R 3 , which are the same or different, represent a hydrogen atom, a carboxyl group, an optionally substituted C1-6 alkyl group, an optionally substituted C6-10 aryl group, or a group represented by —C (═R 9 )—R 10 ), a pharmaceutical composition for treatment or prophylaxis of diseases or disorders that pyruvate dehydrogenase kinase relates to its development or aggravation, and a cosmetic composition, and the like.

  本发明提供了一种新型丙酮酸脱氢酶激酶抑制剂。一种丙酮酸脱氢酶激酶抑制剂包括一种以通式(I)表示的化合物作为活性成分（其中，环A代表一个6-成员芳香碳氢环，可选择地取代有2-4个取代基，R1和R4，它们相同或不同，代表氢原子，羟基，可选择地取代的C1-6烷基基团，R2和R3，它们相同或不同，代表氢原子，羧基，可选择地取代的C1-6烷基基团，可选择地取代的C6-10芳基基团，或由—C(═R9)—R10表示的基团），一种用于治疗或预防与丙酮酸脱氢酶激酶有关的疾病或紊乱的药物组合物，以及一种化妆品组合物等。
• A rapid and efficient novel synthesis of 1,4-dioxo-1,4-dihydronaphthalen-2-yl-1,4-dihydropyridines under green conditions
  作者：Challa Madhavi、Suresh Maddila、Palakondu Lavanya、Sreekantha B. Jonnalagadda

  DOI：10.1016/j.inoche.2023.110906

  日期：2023.8

  BET techniques were utilized for the characterization of as-prepared nanocomposite. Broad substrate scope, mild reaction condition, excellent yield (93–98%) in short reaction time, use of non-toxic solvents, no usage of column chromatography are the various benefits of present synthetic route. The nano-composite was recycled and reused up to seven runs without significant loss in its catalytic activity

  1,4-二氢吡啶支架因其存在于具有不同生物活性的各种天然产物中而引起了合成化学和药物化学的广泛兴趣。在此，我们报道了一种介孔 CeO 2制备的掺杂 HAp 纳米复合材料及其在 1,4-二氧代-1,4-二氢萘-2-基-1,4-二氢吡啶类似物的简易合成中的催化潜力。P-XRD、SEM、SEM-EDX、HRTEM 和 BET 技术用于表征所制备的纳米复合材料。底物范围广、反应条件温和、反应时间短、收率高 (93-98%)、使用无毒溶剂、不使用柱层析是目前合成路线的各种优点。纳米复合材料被回收和重复使用多达七次，而其催化活性没有明显损失。
• Lewis acid mediated allylation of 2-alkanoyl-1,4-quinones with allylsilane and allylstannane
  作者：Yoshinori Naruta、Hidemitsu Uno、Kazuhiro Maruyama

  DOI：10.1016/s0040-4039(01)92464-5

  日期：——
• Allylation of 2-alkanoyl 1,4-quinones with allylsilanes and allylstannanes. Efficient synthesis of pyranonaphthoquinone antibiotics
  作者：Hidemitsu Uno

  DOI：10.1021/jo00353a015

  日期：1986.2
• NARUTA, YOSHINORI;UNO, HIDEMITSU;MARUYAMA, KAZUHIRO, TETRAHEDRON LETT., 1981, 22, N 51, 5221-5224
  作者：NARUTA, YOSHINORI、UNO, HIDEMITSU、MARUYAMA, KAZUHIRO

  DOI：——

  日期：——