2-chloro-3-(α-cyano-α-carbethoxy)methyl-1,4-napthoquinone | 25932-81-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-chloro-3-(α-cyano-α-carbethoxy)methyl-1,4-napthoquinone
• 英文别名: 2-chloro-3-(α-cyano-α-ethoxycarbonyl-methyl)-1,4-naphthoquinone；Ethyl-α-(2-chlor-1.4-dihydro-1.4-dioxo-3-naphthyl)-α-cyanoacetate；(3-chloro-1,4-dioxo-1,4-dihydro-naphthalen-2-yl)-cyano-acetic acid ethyl ester；3-Chlor-naphthochinon-(1.4)-cyanessigsaeure-(2)-aethylester；(3-Chlor-1,4-dioxo-1,4-dihydro-[2]naphthyl)-cyan-essigsaeure-aethylester；3-Chlor-2-(carbaethoxy-cyan-methyl)-naphthochinon-(1.4)；Ethyl (3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)(cyano)acetate；ethyl 2-(3-chloro-1,4-dioxonaphthalen-2-yl)-2-cyanoacetate
• CAS: 25932-81-4
• 化学式: C₁₅H₁₀ClNO₄
• 分子量: 303.702
• InChiKey: MQFPUDFVKBOKAR-UHFFFAOYSA-N

物化性质

• 熔点：
  121 °C(Solv: methanol (67-56-1))
• 沸点：
  462.4±45.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  84.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-chloro-3-(α-cyano-α-carbethoxy)methyl-1,4-napthoquinone 在 吡啶 、 乙醇 作用下， 生成 6,11-dioxo-6,11-dihydrobenzo[f]pyrido[1,2-a]indole-12-carbonitrile
  参考文献：
  名称：

  Reactions of Naphthoquinones with Malonic Ester and its Analogs. III. 1-Substituted Phthaloyl- and Phthaloylbenzopyrrocolines¹

  摘要：

  DOI：

  10.1021/ja01562a048
• 作为产物：
  描述：

  2,3-二氯-1,4-萘醌 、 氰乙酸乙酯 在 ammonium hydroxide 作用下， 以 乙醇 为溶剂， 反应 0.33h， 以64%的产率得到2-chloro-3-(α-cyano-α-carbethoxy)methyl-1,4-napthoquinone
  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 and application of ethyl 2-arylazo-4,9-dioxonaphtho[2,3-<i>b</i>]thiophene-3-carboxylate
  作者：D. W. Rangnekar、V. R. Kanetkar、G. S. Shankarling、J. V. Malanker

  DOI：10.1002/jhet.5570360103

  日期：1999.1

  Synthesis of ethyl 2-arylazo-4,9-dioxonaphtho[2,3-b]thiophene-3-carboxylate was achieved by diazotization of ethyl 2-amino-4,9-dioxonaphtho[2,3-b]thiophene-3-carboxylate and coupling with selected N,N-dialkylanilines. The key intermediate ethyl 2-amino-4,9-dioxonaphtho[2,3-b]thiophene-3-carboxylate was synthesized by the condensation of sodium salt of ethyl cyanoacetate with 2,3-dichloro-1,4-naphthoquinone

  2-芳基偶氮-4,9-二dioxonaphtho [2,3的合成b ]噻吩-3-羧酸乙酯用2-氨基-4,9-二dioxonaphtho [2,3-的重氮化实现b ]噻吩-3-羧酸盐并与选定的N，N-二烷基苯胺偶联。关键中间体2-氨基-4,9-二氧杂萘并[2,3- b ]噻吩-3-羧酸乙酯是通过氰基乙酸乙酯的钠盐与2,3-二氯-1,4-萘醌的缩合反应合成的。将2-芳基偶氮-4,9-二氧杂萘并[2,3- b ]噻吩-3-羧酸乙酯作为分散染料应用于聚酯纤维上，研究了它们的染色性能。
• Liebermann, Chemische Berichte, 1899, vol. 32, p. 920
  作者：Liebermann

  DOI：——

  日期：——
• Synthesis and cytotoxicity evaluation of 2-amino- and 2-hydroxy-3-ethoxycarbonyl- N -substituted-benzo[ f ]indole-4,9-dione derivatives
  作者：Hyun-Jung Lee、Myung-Eun Suh、Chong-Ock Lee

  DOI：10.1016/s0968-0896(03)00062-2

  日期：2003.4

  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.
• AKIBA M.; IKUTA S.; TAKADA T., HETEROCYCLES,1978, 9, NO 7, 813-818
  作者：AKIBA M.、 IKUTA S.、 TAKADA T.

  DOI：——

  日期：——
• Akiba,M. et al., Heterocycles, 1978, vol. 9, # 7, p. 813 - 818
  作者：Akiba,M. et al.

  DOI：——

  日期：——

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