1-(1,4-dihydroxynaphthalen-2-yl)butan-1-one | 72827-02-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(1,4-dihydroxynaphthalen-2-yl)butan-1-one
• 英文别名: 1-(1,4-dihydroxy-2-naphthyl)-1-butanone
• CAS: 72827-02-2
• 化学式: C₁₄H₁₄O₃
• 分子量: 230.263
• InChiKey: AWEJJLXSMBKMDX-UHFFFAOYSA-N

物化性质

• 熔点：
  147-148.5 °C(Solv: chloroform (67-66-3))
• 沸点：
  446.0±30.0 °C(Predicted)
• 密度：
  1.244±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 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-(1,4-dihydroxynaphthalen-2-yl)butan-1-one 在 magnesium sulfate 、 silver(l) oxide 作用下， 以 苯 为溶剂， 生成
  参考文献：
  名称：

  2-酰基-1,4-醌的光化学二聚反应

  摘要：

  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。

  DOI：

  10.1246/bcsj.52.3019
• 作为产物：
  描述：

  1,4-二羟基萘 在 盐酸 、 三氯化铝 、 硫酸 作用下， 反应 8.5h， 生成 1-(1,4-dihydroxynaphthalen-2-yl)butan-1-one
  参考文献：
  名称：

  A new synthesis of anthraquinones

  摘要：

  DOI：

  10.1021/jo01305a029

文献信息

• Photoacylation of Electron-Rich Quinones: An Application of the ”Photo-Friedel-Crafts Reaction”
  作者：Jochen Mattay、Christian Schiel、Michael Oelgemöller

  DOI：10.1055/s-2001-15072

  日期：——

  Irradiation of substituted 1,4-benzo- or 1,4-naphthoquinones in the presence of several aldehydes resulted in the formation of acylated hydroquinones in good yields. In the case of 5-acetyloxy naphthoquinone 8, both regioisomers were formed, but the 2,8-isomer was favored in all cases examined. Even acylated tetrahydroxy naphthalenes became available in good yields by this method.

  在多种醛的存在下，对取代的1,4-苯醌或1,4-萘醌进行辐照，得到了良好产率的酰基化氢醌。在5-乙酰氧基萘醌8的情况下，形成了两种区域异构体，但在所有检查的案例中，2,8-异构体都是优先形成的。通过这种方法，甚至获得了良好产率的酰基化四羟基萘。
• Access to New Cytotoxic Quinone-Amino Acid Conjugates Linked through A Vinylic Spacer from 2-Acylnaphthoquinones and Methyl 3-Aminocrotonate
  作者：Jaime Valderrama、Joel Garrido、Virginia Delgado、Julio Benites、Cristina Theoduloz

  DOI：10.3390/molecules22122281

  日期：——

  bonded through a vinyl spacer in the yields range 40-71%. The presence of not-separable isomers of the naphthoquinone amino acids conjugates in the ¹H- and 13C-NMR spectra is explained by the existence of conformational isomers generated by hindered rotation of the substituent bonded to the quinone double bond. These new naphthoquinone amino acids conjugates were screened in vitro on normal and cancer cell

  2-乙酰基和2-苯甲酰基-1,4-萘醌与（Z）-3-（羟甲基）氨基巴豆酸甲酯的反应通过正式的[3 + 3]过程进行，从而在63中得到相应的1,2-二氢苯并异喹啉喹啉％和72％的收率分别。2-酰基-1，4-萘醌与衍生自不同的1-和d-氨基酸甲基酯的烯胺酮的反应产生了通过乙烯基间隔基键合的相应的萘醌氨基酸共轭物，产率范围为40-71％。在1 H-和13 C-NMR光谱中萘醌氨基酸共轭物的不可分离的异构体的存在是由于存在由于与醌双键结合的取代基的旋转受阻而产生的构象异构体。
• In Vitro Inhibition of Hsp90 Protein by Benzothiazoloquinazolinequinones Is Enhanced in The Presence of Ascorbate. A Preliminary In Vivo Antiproliferative Study
  作者：Jaime A. Valderrama、David Ríos、Giulio G. Muccioli、Pedro Buc Calderon、Julio Benites

  DOI：10.3390/molecules25040953

  日期：——

  A series of benzo[g]benzothiazolo[2,3-b]quinazoline-7,12-quinones were prepared from 2-acylnaphthohydroquinones and 2-aminobenzothiazoles and were evaluated for their in vitro antiproliferative activity. After screening using the MTT reduction assay, their IC50 values were calculated on a panel of cancer cells (T24, DU-145, MCF-7). Current standard anticancer drugs were included as control, and their calculated IC50 values were 7.8 and 23.5 µM for 5-fluorouracil and tamoxifen, respectively. Non-cancer cells (AG1523) were included to assess cancer cell sensitivity and drug selectivity. Four members of the series, with IC50 values from 0.11 to 2.98 µM, were chosen for further assays. The selected quinones were evaluated regarding their effects on cancer cell proliferation (clonogenic assay) and on Hsp90 and poly(ADPribose)polymerase (PARP) protein integrity. The most active compound (i.e., 15) substantially inhibited colony forming unit (CFU) formation at 0.25 µM. In the presence of ascorbate, it induced an oxidative cleavage of Hsp90 but had no effect on PARP protein integrity. In an in vivo animal model, it discreetly increased the mean survival time (m.s.t.) of tumor-bearing mice. In light of these results, compound 15 represents a potential lead-molecule to be further developed.

  一系列苯并[g]苯并噻唑[2,3-b]喹唑啉-7,12-醌类化合物是通过2-酰基萘羟喹醌和2-氨基苯并噻唑反应制备的，并对它们的体外抗增殖活性进行了评估。通过MTT还原实验筛选后，在一系列癌细胞（T24、DU-145、MCF-7）中计算了它们的IC50值。当前标准的抗癌药物被包括为对照，5-氟尿嘧啶和他莫昔芬的计算IC50值分别为7.8和23.5微米。非癌细胞（AG1523）被包括以评估癌细胞的敏感性和药物选择性。系列中的四个成员，其IC50值从0.11到2.98微米不等，被选定进行进一步的实验。选定的醌类化合物被评估其对癌细胞增殖（克隆形成实验）以及对Hsp90和聚(ADP核糖)聚合酶（PARP）蛋白完整性的影响。最活性的化合物（即15号）在0.25微米下显著抑制了克隆形成单位（CFU）的形成。在抗坏血酸存在的情况下，它诱导了Hsp90的氧化裂解，但对PARP蛋白的完整性没有影响。在体内动物模型中，它轻微增加了携带肿瘤的小鼠的平均存活时间（m.s.t.）。鉴于这些结果，化合物15代表了一个有潜力进一步开发的先导分子。
• Synthetic approaches and in vitro cytotoxic evaluation of 2-acyl-3-(3,4,5-trimethoxyanilino)-1,4-naphthoquinones
  作者：Jaime A. Valderrama、Mónica Cabrera、Julio Benites、David Ríos、Ricardo Inostroza-Rivera、Giulio G. Muccioli、Pedro Buc Calderon

  DOI：10.1039/c7ra03238b

  日期：——

  formation of the heterocyclic compounds is discussed in terms of the ring closure of C–C Michael type adduct intermediates through two alternative N–C-bond formations. The propensity of the substrates to undergo preferential C–C instead of C–N bond formation and the further heterocyclization of the C–C Michael type adduct intermediates is rationalized by using product stability parameters assessed by DFT

  2-酰基-1,4-萘醌与3,4,5-三甲氧基苯胺在有氧条件下反应，生成苯并菲啶醌，苯并咔唑和2-酰基-3-（3,4,5-三甲氧基苯胺基）-1,4-萘醌衍生品。关于杂环化合物的形成，将通过两个备选的N-C键形成对C–C Michael型加合物中间体的闭环进行讨论。通过使用DFT计算评估的产品稳定性参数，可以使底物发生优先C–C而不是C–N键形成的倾向以及C–C Michael型加合物中间体的进一步杂环化。初步结果报道了从2-酰基萘醌制备2-酰基-3-（3,4,5-三甲氧基苯胺基）-1,4-萘醌的便利方法及其对癌细胞的细胞毒活性。
• An Improved Procedure for the Photoacylation of 1,4-Naphthoquinone with Aliphatic Aldehydes
  作者：Michael Oelgemöller、Ferdinand Friedrichs、Brian Murphy、Delphine Nayrat、Torsten Ahner、Mario Funke、Michael Ryan、Johann Lex、Jochen Mattay

  DOI：10.1055/s-0028-1087272

  日期：——

  Irradiation of 1,4-naphthoquinone at 300±25 nm in benzene and in the presence of aliphatic aldehydes readily yields acylated hydroquinones in good to high yields. The developed protocol represents a significant improvement over the original procedure using medium-pressure mercury lamps. Subsequent oxidation gives the corresponding acylated quinones.

  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。