2-N-morpholino-dithiocarbamoyl-pentanoic acid | 181036-27-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-N-morpholino-dithiocarbamoyl-pentanoic acid
• 英文别名: 2-(Morpholine-4-carbothioylsulfanyl)pentanoic acid
• CAS: 181036-27-1
• 化学式: C₁₀H₁₇NO₃S₂
• 分子量: 263.382
• InChiKey: IIEZIHYPSQNMLF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  107
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-N-morpholino-dithiocarbamoyl-pentanoic acid 在 二硫化碳 、 乙酸酐 、 三乙胺 作用下， 以 苯 为溶剂， 以75%的产率得到2-N-morpholino-5-propyl-1,3-dithiolium-4-thiolate
  参考文献：
  名称：

  MESOIONIC 2-N-CYCLOALKYLAMINO-5-ALKYL-1,3-DITHIOLIUM-4-THIOLATES

  摘要：

  Seven 2-(N-cycloalkylamino-1,3-dithiocarbamoyl)-carboxylic acids and seven mesoionic 2-N-cycloalkylamino-5-alkyl-1,3-dithiolium-4-thiolates have been conveniently synthesized. They were characterized by elemental analysis, I.R., U.V., mass and H-1 NMR spectrometry, plus C-13 NMR spectrometry in some cases. Important questions concerning the structure of the mesoionic compounds, relevant to mesoionic compounds in general, are addressed. In particular, we refer to the degree of separation of regions of positive and negative charge, bond orders, electron and charge delocalization and aromaticity. In this discussion we cite some of our X-ray diffraction and theoretical studies. We conclude that there are regions of positive and negative charge in which there is delocalization of electrons and charge with bond orders between 1 and 2. However, the shared regions are separated by what are essentially single bonds. Thus, they, and mesoionic compounds in general, should not be considered as formally aromatic. This is supported by estimates of Bird Aromaticity indices-experimentally based for two of the title mesoionic compounds-of the order of 50: substantially less than values for thiophene and pyrrole and much less than values for benzene and pyridine. Finally, based on this discussion, we introduce a new notation for the structures of mesoionic compounds which we believe more accurately represents both the bonding situation and the chemical patterns of reactivity of such compounds.

  DOI：

  10.1080/10426509608029640
• 作为产物：
  描述：

  正戊酸 在 溴 、 三氯化磷 作用下， 以 苯 为溶剂， 反应 31.0h， 生成 2-N-morpholino-dithiocarbamoyl-pentanoic acid
  参考文献：
  名称：

  中离子 5-ALKYL-1,3-DITHIOLIUM-4-THIOLATES：合成和盐水对虾的毒性

  摘要：

  合成并表征了一系列 12 种 1,3-dithiolium-4-thiolate 介离子化合物。以α-溴代链烷酸为原料合成2-N-吗啉代-二硫代氨基甲酰基羧酸，在甲胺中与二硫化碳和乙酸酐反应生成相应的2-N-吗啉代-二硫代氨基甲酰羧酸，未分离出中间体1,3-二硫鎓-4-油酸酯。之后，通过逆向 1,3-偶极加成反应获得 2-N-morpholino-5-烷基-1,3-dithiolium-4-thiolates。醇！与杂环的 C-5 连接的部分允许增加疏水特性，并且对卤虫的致死率评估了这种影响。结果表明，介离子衍生物侧链碳原子数与丰年虾毒性测定的LD50呈钟形关系。介离子化合物因其特殊的结构、反应行为和广谱性而受到越来越多的关注和广泛的研究。 -范围的生物活动 (1-5)。最近，这些化合物已被广泛用于新材料应用，包括非线性光学效应 (6)、分析试剂 (7)（例如 Nitron"）和照相材料

  DOI：

  10.1515/hc.2002.8.6.593

文献信息

• MESOIONIC 5-ALKYL-1,3-DITHIOLIUM-4-THIOLATES: SYNTHESIS AND BRINE SHRIMP TOXICITY
  作者：Paulo Afonso de Almeida、Tänia Maria Sarmento da Silva、Aurea Echevarria

  DOI：10.1515/hc.2002.8.6.593

  日期：2002.1

  A series of twelve 1,3-dithiolium-4-thiolate mesoionic compounds were synthesized and characterized. The synthetical approach starting from α-bromoalkancic acids to obtain the corresponding 2-N-morpholino-dithiocarbamoylcarboxylic acids that by on-pot reaction with carbon disulfide and acetic anhydride in Methylamine formed not isolate intermediates, 1,3-dithiolium-4-olates. After, the 2-N-morpholino-5-alkyl-1

  合成并表征了一系列 12 种 1,3-dithiolium-4-thiolate 介离子化合物。以α-溴代链烷酸为原料合成2-N-吗啉代-二硫代氨基甲酰基羧酸，在甲胺中与二硫化碳和乙酸酐反应生成相应的2-N-吗啉代-二硫代氨基甲酰羧酸，未分离出中间体1,3-二硫鎓-4-油酸酯。之后，通过逆向 1,3-偶极加成反应获得 2-N-morpholino-5-烷基-1,3-dithiolium-4-thiolates。醇！与杂环的 C-5 连接的部分允许增加疏水特性，并且对卤虫的致死率评估了这种影响。结果表明，介离子衍生物侧链碳原子数与丰年虾毒性测定的LD50呈钟形关系。介离子化合物因其特殊的结构、反应行为和广谱性而受到越来越多的关注和广泛的研究。 -范围的生物活动 (1-5)。最近，这些化合物已被广泛用于新材料应用，包括非线性光学效应 (6)、分析试剂 (7)（例如 Nitron"）和照相材料
• MESOIONIC 2-N-CYCLOALKYLAMINO-5-ALKYL-1,3-DITHIOLIUM-4-THIOLATES
  作者：Magali B. De Oliveira、Joseph Miller、Arnaldo B. Pereira、Sérgio E. Galembeck、Gustavo L. C. De Moura、Alfredo M. Simas

  DOI：10.1080/10426509608029640

  日期：1996.1.1

  Seven 2-(N-cycloalkylamino-1,3-dithiocarbamoyl)-carboxylic acids and seven mesoionic 2-N-cycloalkylamino-5-alkyl-1,3-dithiolium-4-thiolates have been conveniently synthesized. They were characterized by elemental analysis, I.R., U.V., mass and H-1 NMR spectrometry, plus C-13 NMR spectrometry in some cases. Important questions concerning the structure of the mesoionic compounds, relevant to mesoionic compounds in general, are addressed. In particular, we refer to the degree of separation of regions of positive and negative charge, bond orders, electron and charge delocalization and aromaticity. In this discussion we cite some of our X-ray diffraction and theoretical studies. We conclude that there are regions of positive and negative charge in which there is delocalization of electrons and charge with bond orders between 1 and 2. However, the shared regions are separated by what are essentially single bonds. Thus, they, and mesoionic compounds in general, should not be considered as formally aromatic. This is supported by estimates of Bird Aromaticity indices-experimentally based for two of the title mesoionic compounds-of the order of 50: substantially less than values for thiophene and pyrrole and much less than values for benzene and pyridine. Finally, based on this discussion, we introduce a new notation for the structures of mesoionic compounds which we believe more accurately represents both the bonding situation and the chemical patterns of reactivity of such compounds.