2-cyano-3,3-dimercapto-2-propenoic acid methyl ester | 74598-57-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-cyano-3,3-dimercapto-2-propenoic acid methyl ester
• 英文别名: 2,3-Dimercapto-maleinsaeure-nitril-methylester；Methyl 2-cyano-3,3-bis(sulfanyl)prop-2-enoate
• CAS: 74598-57-5
• 化学式: C₅H₅NO₂S₂
• 分子量: 175.232
• InChiKey: MLDYHZVEEOMUPZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  52.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-cyano-3,3-dimercapto-2-propenoic acid methyl ester 以 乙醇 、 乙腈 为溶剂， 100.0 ℃ 、689.49 kPa 条件下， 反应 0.5h， 生成 methyl 3-[[bis(2-ethoxyethoxy)phosphoryl-phenylmethyl]amino]-2-cyano-3-methylsulfanylprop-2-enoate
  参考文献：
  名称：

  Synthesis and Antiviral Bioactivities of 2-Cyano-3-substituted-amino(phenyl) Methylphosphonylacrylates (Acrylamides) Containing Alkoxyethyl Moieties

  摘要：

  An efficient reaction under microwave irradiation has been developed for the synthesis of a series of novel 2-cyano-3-substituted-amino(phenyl) methylphosphonylacrylates (acrylamides) II. The products obtained in shorter reaction time with moderate yields are fully characterized by elemental analysis, IR, H-1, C-13, and P-31 NMR spectral data. The role of introducing various substituents and the effect of incorporating alpha-aminophosphonates with an alkoxyethyl moiety into the parent cyanoacrylate (acrylamide) structure are investigated. Among the studied compounds, both II-17 and II-24 displayed good in vivo curative, protection, and inactivation effects, which were comparable to those of the commercial reference ningnanmycin (inhibitory rates of 58.8, 60.2, 78.9% and 60.0, 58.9, 85.5%, respectively, at 500 mg/L against TMV). To the best of the authors' knowledge, this is the first report on the synthesis and antiviral activity of the title compounds II.

  DOI：

  10.1021/jf902861m
• 作为产物：
  描述：

  二硫化碳 、 氰乙酸甲酯 在 sodium methylate 、 sodium 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 2-cyano-3,3-dimercapto-2-propenoic acid methyl ester
  参考文献：
  名称：

  A regioselective synthesis of 2,6-diarylpyridines

  摘要：

  通过碱（二甲基亚砜中的氢氧化钠）催化的环转变反应，从适当功能化的2H-吡喃-2-酮与苯甲酰胺的区域选择性合成2,6-二芳基吡啶已被详细阐述。然而，在无水乙醇中使用氢氧化钠作为催化剂，2H-吡喃-2-酮与苯甲酰胺的类似反应产生了高度拥挤的δ-酮酯，具有活性甲烯中心，而不是2,6-二芳基吡啶。

  DOI：

  10.1039/c3ra41575a

文献信息

• Organic photoelectric device image sensor and electronic device
  申请人：Samsung Electronics Co., Ltd.

  公开号：US09997718B2

  公开（公告）日：2018-06-12

  An organic photoelectric device includes a first electrode and a second electrode facing each other, and an active layer between the first electrode and the second electrode, the active layer including an n-type semiconductor compound represented by Chemical Formula 1 and a p-type semiconductor compound having selective light absorption in a green wavelength region of about 500 nm to about 600 nm.

  一种有机光电器件包括相互面对的第一电极和第二电极，以及位于第一电极和第二电极之间的活性层，该活性层包括由化学式1表示的n型半导体化合物和具有选择性吸收约500nm至约600nm绿色波长区域光的p型半导体化合物。
• Soederbaeck,E., Acta Chemica Scandinavica (1947), 1963, vol. 17, p. 362 - 376
  作者：Soederbaeck,E.

  DOI：——

  日期：——
• ZONTOVA, V. N.;KOROLEVA, T. I.;NEGREBETSKIJ, V. V.;GRAPOV, A. F., ZH. OBSHCH. XIMII, 60,(1990) N, S. 475-476
  作者：ZONTOVA, V. N.、KOROLEVA, T. I.、NEGREBETSKIJ, V. V.、GRAPOV, A. F.

  DOI：——

  日期：——
• Synthesis and Antiviral Bioactivities of 2-Cyano-3-substituted-amino(phenyl) Methylphosphonylacrylates (Acrylamides) Containing Alkoxyethyl Moieties
  作者：Jia-Qiang Yang、Bao-an Song、Pinaki S. Bhadury、Zhuo Chen、Song Yang、Xue-Jian Cai、De-Yu Hu、Wei Xue

  DOI：10.1021/jf902861m

  日期：2010.3.10

  An efficient reaction under microwave irradiation has been developed for the synthesis of a series of novel 2-cyano-3-substituted-amino(phenyl) methylphosphonylacrylates (acrylamides) II. The products obtained in shorter reaction time with moderate yields are fully characterized by elemental analysis, IR, H-1, C-13, and P-31 NMR spectral data. The role of introducing various substituents and the effect of incorporating alpha-aminophosphonates with an alkoxyethyl moiety into the parent cyanoacrylate (acrylamide) structure are investigated. Among the studied compounds, both II-17 and II-24 displayed good in vivo curative, protection, and inactivation effects, which were comparable to those of the commercial reference ningnanmycin (inhibitory rates of 58.8, 60.2, 78.9% and 60.0, 58.9, 85.5%, respectively, at 500 mg/L against TMV). To the best of the authors' knowledge, this is the first report on the synthesis and antiviral activity of the title compounds II.
• A regioselective synthesis of 2,6-diarylpyridines
  作者：Hardesh K. Maurya、Prema G. Vasudev、Atul Gupta

  DOI：10.1039/c3ra41575a

  日期：——

  A regioselective synthesis of 2,6-diarylpyridines through base (sodium hydroxide in DMSO) catalyzed ring transformation of suitably functionalized 2H-pyran-2-ones with benzamide has been delineated. However, similar reaction of 2H-pyran-2-ones with benzamide using sodium hydroxide in absolute ethanol yielded highly congested delta keto esters with an active methylene centre, instead of 2,6-diarylpyridines.

  通过碱（二甲基亚砜中的氢氧化钠）催化的环转变反应，从适当功能化的2H-吡喃-2-酮与苯甲酰胺的区域选择性合成2,6-二芳基吡啶已被详细阐述。然而，在无水乙醇中使用氢氧化钠作为催化剂，2H-吡喃-2-酮与苯甲酰胺的类似反应产生了高度拥挤的δ-酮酯，具有活性甲烯中心，而不是2,6-二芳基吡啶。