2-propionyl-1,4-naphthoquinone | 14777-30-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-propionyl-1,4-naphthoquinone
• 英文别名: 1,4-Naphthalenedione, 2-(1-oxopropyl)-；2-propanoylnaphthalene-1,4-dione
• CAS: 14777-30-1
• 化学式: C₁₃H₁₀O₃
• 分子量: 214.221
• InChiKey: RDZZFOBERIJIJN-UHFFFAOYSA-N

物化性质

• 沸点：
  387.0±42.0 °C(Predicted)
• 密度：
  1.272±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 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-propionyl-1,4-naphthoquinone 在 ammonium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.0h， 生成 6-Ethyl-1,2,3,4-tetrahydrobenzo[j]phenanthridine-7,12-dione
  参考文献：
  名称：

  One-pot synthesis of isoquinoline-5,8-dione derivatives from acylquinones and enamines

  摘要：

  A new and facile method for the preparation of isoquinolinequinone derivatives has been developed. Treatment of l-acyl-l,4-naphthoquinones or 2-acyl-5,6-dimethyl-1,4-benzoquinones with enamines (or imines), followed by addition of aqueous NH3 in MeOH afforded benz[g]isoquinoline-5,10-dione or isoquinoline-5,8-dione derivatives, respectively, in moderate to good yields. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01313-7
• 作为产物：
  描述：

  1-(1,4-dihydroxynaphthalen-2-yl)propan-1-one 在 sodium sulfate 、 silver(l) oxide 作用下， 以 乙醚 为溶剂， 以92%的产率得到2-propionyl-1,4-naphthoquinone
  参考文献：
  名称：

  1,4-萘醌与脂肪醛光酰化的改进方法

  摘要：

  1,4-萘醌在苯中和脂肪醛存在下以 300±25 nm 进行辐照，很容易以良好到高产率产生酰化氢醌。开发的协议代表了对使用中压汞灯的原始程序的重大改进。随后的氧化得到相应的酰化醌。

  DOI：

  10.1055/s-0028-1087272

文献信息

• TYPE 1, 4-NAPHTOQUINONE COMPOUNDS, COMPOSITIONS COMPRISING THEM AND USE OF THESE COMPOUNDS AS ANTI-CANCER AGENTS
  申请人：Depierre Gaelle

  公开号：US20090247472A1

  公开（公告）日：2009-10-01

  This invention relates to compounds with the formula (I) given below or one of their pharmaceutically acceptable salts, as a medicine; Formula (I) of pharmaceutical compositions comprising one or more compounds with Formula (I) as active constituent, use of compounds with Formula (I) for the preparation of compositions designed to prevent or treat at least one illness involving an abnormal cellular proliferation, pro-apoptotic compositions and/or anti-proliferative compositions comprising at least one compound with Formula (I)/and the use of compounds with formula (I) as pro-apoptotic and/or anti-proliferative agents.

  这项发明涉及以下给定的化合物（I）的公式或其药学上可接受的盐之一，作为药物；包含一个或多个具有公式（I）的化合物作为活性成分的药物组合物的公式（I），使用具有公式（I）的化合物制备旨在预防或治疗涉及异常细胞增殖的至少一种疾病的组合物，包含至少一种具有公式（I）的化合物的促凋亡组合物和/或抗增殖组合物，以及使用具有公式（I）的化合物作为促凋亡和/或抗增殖剂。
• Non-Catalyzed Thermal Reactions of Acylquinones with Allylstannanes
  作者：Kazuhiro Maruyama、Yoshihiro Matano

  DOI：10.1246/bcsj.62.3877

  日期：1989.12

  Thermal reactions of acylquinones with allylstannanes in benzene afforded several kinds of product after column chromatography on silica gel; acyl allyl quinones, acyl allyl epoxy quinones, cyclopentanoid compounds including stannyl moiety, allyl hydroxy quinones, acyl hydroquinones, and acyl allyl hydroquinones. The main product comprises cyclopentanoid compounds, which are novel [2+3] cyclo adducts with 1,2-migration of trialkylstannyl moiety. Spectroscopic examinations (1H NMR and Vis-UV) enabled us to confirm the reaction pathways that four types of precursors were initially generated via polarized tight pair and inverted to isolated products during purification by column chromatography. Similar reactions in acetonitrile showed a remarkable difference in the reactivity, that is, acyl allyl quinones and the corresponding hydroquinones are obtained, but the [2+3] cyclo adducts are not produced at all. From 1H NMR examination, it was confirmed that three types of precursor are generated via solvent separated ion pairs at the initial stage. The rather strong reactivity of acylquinones towards allylstannanes will be due to electron withdrawing ability of acyl group.

  酰基喹诺酮与烯丙基锡在苯中的热反应经过硅胶柱层析后产生了几种产品；包括酰基烯丙基喹诺酮、酰基烯丙基环氧喹诺酮、含锡基团的环戊烷类化合物、烯丙基羟基喹诺酮、酰基羟基喹诺酮和酰基烯丙基羟基喹诺酮。主要产品是环戊烷类化合物，它们是新型的 [2+3] 环加成物，具有三烷基锡基团的 1,2-迁移。通过光谱学检查（1H NMR 和 Vis-UV），我们确认了反应途径，四种前体最初通过极化紧配对生成，并在柱层析纯化过程中转化为孤立的产品。在乙腈中的类似反应显示出明显的反应性差异，即生成酰基烯丙基喹诺酮及其对应的羟基喹诺酮，但完全不产生 [2+3] 环加成物。从 1H NMR 检查中确认，三种类型的前体在初始阶段通过溶剂分离离子对生成。酰基喹诺酮对烯丙基锡的较强反应性将是由于酰基的电子吸引能力。
• The Photochemical Dimerization of 2-Acyl-1,4-quinones
  作者：Yo Miyagi、Kazuhiro Maruyama、Hideo Ishii、Sachie Mizuno、Masao Kakudo、Nobuo Tanaka、Yoshiki Matsuura、Shigeharu Harada

  DOI：10.1246/bcsj.52.3019

  日期：1979.10

  2-Acyl-1,4-benzoquinones and 2-acyl-1,4-naphthoquinones underwent a novel type of regiospecific and stereospecific cyclodimerization by photolysis. The reaction was general, being not affected by a...

  2-Acyl-1,4-benzoquinones 和 2-acyl-1,4-naphthoquinones 通过光解经历了一种新型的区域专一性和立体专一性环二聚化。反应是一般的，不受...的影响。
• PHOTOCHEMICAL DIMERIZATION OF 2-ACYL-1,4-QUINONES
  作者：Yo Miyagi、Kazuo Kitamura、Kazuhiro Maruyama、Yuan Lang Chow

  DOI：10.1246/cl.1978.33

  日期：1978.1.5

  Upon irradiation 2-acyl-1,4-quinones (I) underwent a regiospecific condensation to give their dimers, polycyclic compounds (II). An alternative structure (II′), though it is compatible with the NMR spectra of the dimers, was excluded on the basis of converting one of the dimers to a 9,10-phenanthrenequinone derivative (IV). No condensation of I with dienophiles occurred.

  在辐射后，2-酰基-1,4-醌（I）经历了区域特异性缩合，得到它们的二聚体，多环化合物（II）。替代结构 (II') 尽管与二聚体的 NMR 谱相容，但基于将其中一个二聚体转化为 9,10-菲醌衍生物 (IV) 而排除在外。没有发生 I 与亲二烯体的缩合。
• 10.1002/1099-0690(200208)2002:15<2465::aid-ejoc2465<3.0.co;2-o
  作者：Oelgemoeller, Michael、Schiel, Christian、Froehlich, Roland、Mattay, Jochen

  DOI：10.1002/1099-0690(200208)2002:15<2465::aid-ejoc2465<3.0.co;2-o

  日期：——