diethyl (3-chloro-1,4-naphthoquinone-2-yl)malonate | 18093-48-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: diethyl (3-chloro-1,4-naphthoquinone-2-yl)malonate
• 英文别名: (3-chloro-1,4-dioxo-1,4-dihydro-[2]naphthyl)-malonic acid diethyl ester；(3-Chlor-1,4-dioxo-1,4-dihydro-[2]naphthyl)-malonsaeure-diaethylester；3-Chlor-naphthochinon-(1.4)-malonsaeure-(2)-diaethylester；3-Chlor-2-(dicarbaethoxy-methyl)-naphthochinon-(1.4)；3-Chlor-2-bis(ethoxycarbonyl)methylnaphthoquinon；1,3-Diethyl 2-(3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)propanedioate；diethyl 2-(3-chloro-1,4-dioxonaphthalen-2-yl)propanedioate
• CAS: 18093-48-6
• 化学式: C₁₇H₁₅ClO₆
• 分子量: 350.755
• InChiKey: NVIOHKNIBIOJJW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  86.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  diethyl (3-chloro-1,4-naphthoquinone-2-yl)malonate 以70%的产率得到
  参考文献：
  名称：

  SALOV B. V.; SHAXNOVICH A. I., XIMIYA GETEROTSIKL. SOEDIN. , 1976, HO 7, 911-914

  摘要：

  DOI：
• 作为产物：
  描述：

  2,3-二氯-1,4-萘醌 、 丙二酸二乙酯 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 0.12h， 以27%的产率得到diethyl (3-chloro-1,4-naphthoquinone-2-yl)malonate
  参考文献：
  名称：

  Synthesis and cytotoxicity evaluation of 2-amino- and 2-hydroxy-3-ethoxycarbonyl- N -substituted-benzo[ f ]indole-4,9-dione derivatives

  摘要：

  Reaction between 2,3-dichloronaphthoquinone (I) and ethyl cyanoacetate or diethyl malonate under different conditions gave the starting materials, 2-chloro-3-(alpha-cyano-alpha-ethoxycarbonyl-methyl)-1,4-naphthoquinone (A) or 2-chloro-3-(diethoxycarbonyl-methyl)-1,4-naphthoquinone (B). The 2-amino-3-ethoxycarbonyl-N-substituted-benzo[f]indole-4,9-dione derivatives [A-(1-10)] and 2-hydroxy-3-ethoxycarbonyl-N-substituted-benzo[f]indole-4,9-dione derivatives [B-(1-12)] were prepared from compounds A and B, respectively, by using various alkyl-, and arylamines. The cytotoxic activities of the prepared compounds were evaluated by SRB (Sulforhodamine B) assay against the following tumor cell lines: A459 (human lung), SK-OV-3 (human ovarian), SK-MEL-2 (human melanoma), XF498 (human CNS), and HCT 15 (human colon). Many of the derivatives mentioned exhibited more potent cytotoxic effects against SK-OV-3 and XF498 than etoposide. Significantly, 2-amino-3-ethoxycarbonyl-N-(3-methyl-phenyl)-benzo[f]indole-4,9-dione (A-8) showed potent activity against all tumor cell lines, and in particular, its cytotoxic effect against SK-OV-3 was much higher than doxorubicin. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00062-2

文献信息

• Synthesis of Novel Polycyclic Selenepinone Compounds
  作者：Makoto Sakakibara、Takahiro Mizumoto、Yoshihiko Watanabe、Takeshi Toru、Yoshio Ueno

  DOI：10.1246/bcsj.65.1794

  日期：1992.7

  Novel polycyclic selenepinone compounds, benzo[b]naphtho[2,3-f]selenepin-6,11,13(12H)-trione (6) and 6,14-dimethoxybenzo[1,2-b:5,4-b′]bis[1]benzoselenepin-12,16(13H,15H)-dione (14) were synthesized from chloroquinones.

  新型多环硒酮化合物苯并[b]萘并[2,3-f]硒素-6,11,13(12H)-三酮（6）和 6,14-二甲氧基苯并[1,2-b:5,4-b′]双[1]苯并硒素-12,16(13H,15H)-二酮（14）由氯醌类化合物合成。
• Liebermann, Chemische Berichte, 1899, vol. 32, p. 920
  作者：Liebermann

  DOI：——

  日期：——
• Liebermann, Chemische Berichte, 1899, vol. 32, p. 264
  作者：Liebermann

  DOI：——

  日期：——
• Liebermann, Chemische Berichte, 1900, vol. 33, p. 570
  作者：Liebermann

  DOI：——

  日期：——

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