2-(4-chlorophenyl)-3-hydroxynaphthalene-1,4-dione | 10409-20-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(4-chlorophenyl)-3-hydroxynaphthalene-1,4-dione
• 英文别名: 2-(4-chloro-phenyl)-3-hydroxy-[1,4]naphthoquinone；2-(4-Chlor-phenyl)-3-hydroxy-[1,4]naphthochinon；3-(4-Chlor-phenyl)-2-hydroxy-naphtho-1,4-chinon
• CAS: 10409-20-8
• 化学式: C₁₆H₉ClO₃
• 分子量: 284.699
• InChiKey: HWRVFGNFROHXLI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.69
• 重原子数：
  20.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.37
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-(4-chlorophenyl)-3-hydroxynaphthalene-1,4-dione 、 二苯基乙炔 在 palladium diacetate 、 copper(II) acetate monohydrate 作用下， 以 2-甲基-2-丁醇 为溶剂， 反应 12.0h， 以78%的产率得到(E)-3-(5-chloro-2,3-diphenyl-1H-inden-1-ylidene)isobenzofuran- 1(3H)-one
  参考文献：
  名称：

  Pd（II）催化的脱羰环化反应合成亚烷基邻苯二甲酰亚胺

  摘要：

  据报道，空前的Pd（II）催化的脱羰CH-H / CC活化和环化反应是通过分子内环化进行的。羟基萘醌与二取代炔烃的这种反应提供了高收率的取代亚烷基苯酞，这是合成生物活性天然产物的关键中间体。

  DOI：

  10.1021/acs.orglett.9b00726
• 作为产物：
  描述：

  1,4-萘醌 在 sodium hydroxide 、 三氟化硼乙醚 作用下， 生成 2-(4-chlorophenyl)-3-hydroxynaphthalene-1,4-dione
  参考文献：
  名称：

  Fieser et al., Journal of the American Chemical Society, 1948, vol. 70, p. 3177

  摘要：

  DOI：

文献信息

• Styryl and functionalized aryl derivatives of lawsone through metal-free cross-coupling of its BF3-activated phenyliodonium ylide with cinnamaldehydes and arylaldehydes
  作者：Elizabeth Malamidou-Xenikaki、Maria Tsanakopoulou、Maria Chatzistefanou、Dimitra Hadjipavlou-Litina

  DOI：10.1016/j.tet.2015.06.037

  日期：2015.8

  Phenyliodonium ylide of lawsone activated with BF3 center dot Et2O reacts with cinnamaldehydes to afford 2-hydroxy-3-styryl-1,4-naphthoquinones in good to excellent yields and relatively high level of stereospecificity through deformylation of the aldehydes. The product yield is diminished with a methoxy substituted cinnamaldehyde and becomes zero with a dimethoxy substituted substrate giving rise to another product, 2-hydroxy-3-aryl-1,4-naphthoquinone. The reaction of the same ylide with salicylic aldehydes forms 2-hydroxy-3-(2-hydroxyary1)-1,4-naphthoquinones and/or benzo[d]naphtha[2,1-b]furano-5,6-diones, depending on the reaction conditions applied. Plausible reaction mechanisms explaining the formation of these products are proposed. The products showed potent antioxidant activity and inhibited lipoxygenase. (C) 2015 Elsevier Ltd. All rights reserved.
• Arylation of lawsone through BF3-mediated coupling of its phenyliodonium ylide with activated arenes and aromatic aldehydes
  作者：Elias Glinis、Elizabeth Malamidou-Xenikaki、Haris Skouros、Spyros Spyroudis、Maria Tsanakopoulou

  DOI：10.1016/j.tet.2010.04.120

  日期：2010.7

  Phenyliodonium ylide of lawsone, activated by BF3 center dot Et2O, reacts with electron-rich arenes to afford the corresponding 2-aryl-3-hydroxy-1,4-naphthoquinones, in a coupling reaction without metal catalysts. The same type of products, in greater variety and higher yields, are obtained from the reaction of the BF3 center dot Et2O-activated ylide with aromatic aldehydes in a synthetically and mechanistically interesting deformylation reaction. (C) 2010 Elsevier Ltd. All rights reserved.
• SHCHERBAN A. I.; ALEKSYUK M. P.; XARITONOV G. V., IZV. VUZOV. XIMIYA I XIM. TEXNOL.,
  作者：SHCHERBAN A. I.、 ALEKSYUK M. P.、 XARITONOV G. V.

  DOI：——

  日期：——
• Protein p140 and DNA encoding it
  申请人：ONO PHARMACEUTICAL CO., LTD.

  公开号：EP0659883B1

  公开（公告）日：2003-04-16
• Novel polypeptide of protein p140 and DNAs encoding it
  申请人：ONO PHARMACEUTICAL CO., LTD.

  公开号：US20030170865A1

  公开（公告）日：2003-09-11

  The present invention is related to a novel protein p140 polypeptide which is a key protein involved in the signal transmission system of insulin; method for preparation of it; DNA encoding the said polypeptide; vector derived the said DNA; host cells transformed the said vector; antibody of the said polypeptide; pharmaceutical composition containing the said peptide or antibody; method for the prevention and/or treatment of diabetes, which is characterized by tyrosine phosphorylation of the said protein p140; agent for the prevention and/or treatment for the currently said the prevention and/or treatment method; agent for the prevention and/or treatment of diabetes, which is characterized by containing a compound which can tyrosine phosphorylation of protein p140, as active ingredient and the screening methods of the said prevention and/or treatment agent. Tyrosine phosphorylation of protein p140 is an essential step in the induction of hypoglycemia by glucose uptake. Method and agent of prevention and/or treatment based on tyrosine phosphorylation of protein p140 in the present invention is not only improve the diabetes-derived hyperglycemic conditions but are also useful for the treatment and/or prevention of diabetes, especially non-insulin dependent diabetes mellitus (NIDDM).