1,2,2,2-四氯乙基N-甲基氨基甲酸酯 | 101506-45-0

• 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
• 中文名称: 1,2,2,2-四氯乙基N-甲基氨基甲酸酯
• 英文名称: 1,2,2,2-tetrachloroethyl N-methylcarbamate
• CAS: 101506-45-0
• 化学式: C₄H₅Cl₄NO₂
• 分子量: 240.901
• InChiKey: YYUSRRCQGJTZGA-UHFFFAOYSA-N

物化性质

• 沸点：
  249.0±40.0 °C(Predicted)
• 密度：
  1.576±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,2,2,2-四氯乙基N-甲基氨基甲酸酯 、 2-methyl-3-amino-5-[p-[[2-aminoethyl]carbamoyl]phenyl]-7-(dimethylamino)phenazenium chloride 以 1,4-二氧六环 、 水 、 三乙胺 为溶剂， 反应 8.0h， 以38%的产率得到2-methyl-3-amino-5-[p-[[2-[(N-methylcarbamoyl)amino]ethyl]carbamoyl]phenyl]-7-(dimethylamino)phenazenium chloride
  参考文献：
  名称：

  The Design of Agents To Control DNA Methylation Adducts. Enhanced Major Groove Methylation of DNA by an N-Methyl-N-nitrosourea Functionalized Phenyl Neutral Red Intercalator

  摘要：

  An N-methyl-N-nitrosourea (MNU) moiety [CH3N(N=O)C(=O)NH-] linked to the C4'-position of the 5-substituted phenyl ring of phenyl neutral red (PNR), 2-methyl-3-amino-5-[p-[[2-[(N-nitroso-N-methylcarbamoyl)amino]ethyl]carbamoyl]phenyl]-7-(dimethylamino)phenazenium chloride (MNU-PNR), has been synthesized as an approach to design a molecule that will deliver alkylating agents with some preference to guanine (Gua) in the major groove of DNA. The PNR nucleus was chosen because previous studies suggested the following: (1) PNR binds with a slight preference for G/C rich sequences; and (2) PNR intercalates into DNA from the major groove with the 5-phenyl ring pointing out into the major groove (Muller, W., Bunemann, H., and Dattagupta, N. (1975) fur. J. Biochem. 54, 279-291). It is demonstrated that MNU-PNR yields 2.6 and 6.0 times more N7-methylguanine (7-MeGua) than MNU at low salt (10 mM Tris buffer) and high salt (10 mM Tris buffer + 200 mM NaCl), respectively. It is also shown that the ratio of 7-MeGua (a major groove adduct) to N3-methyladenine (a minor groove adduct) is approximately 5 times higher for MNU-PNR than for MNU. The yield of the 7-MeGua adduct is decreased by the coaddition of a nonmethylating analogue of MNU-PNR or NaCl, but increased in the presence of the minor groove intercalator, ethidium bromide. Using a P-32-end-labeled restriction fragment, the enhanced methylation by MNU-PNR at 7-Gua is confirmed, and it is demonstrated that the sequence-dependent formation of 7-MeGua from MNU-PNR is the same as that seen with MNU. UV, circular dichroism, and viscosity studies are consistent with MNU-PNR binding to DNA via an intercalation-based process.

  DOI：

  10.1021/tx960007n
• 作为产物：
  描述：

  (+/-)-1,2,2,2-四氯乙基氯甲酸酯 在 甲胺 作用下， 以 二氯甲烷 、 水 为溶剂， 以88%的产率得到1,2,2,2-四氯乙基N-甲基氨基甲酸酯
  参考文献：
  名称：

  Process for the preparation of carbamates, thiocarbamates and ureas

  摘要：

  本发明涉及一种制备公式为##STR1##的氨基甲酸衍生物的方法，其中R.sup.1或R.sup.2表示氢原子或取代或未取代的、饱和或不饱和的脂肪族、环脂肪族或杂环基团，或者R.sup.1和R.sup.2共同形成一个环，Y表示OR、SR、##STR2##基团，R表示取代或未取代的、饱和或不饱和的脂肪族或环脂肪族基团，或者取代或未取代的芳香族基团，R.sup.3和R.sup.4表示氢原子或脂肪族、环脂肪族、脂环族、芳香族或杂环基团，或者共同形成一个环，R.sup.6和R.sup.7表示饱和或不饱和的、取代或未取代的脂肪族或环脂肪族基团、氢原子、烷基硫基团或烷氧基团。根据本过程，将公式为##STR3##的化合物与公式为##STR4##的α-卤代衍生物在-5至150摄氏度的温度下，在卤化氢酸的受体存在下进行反应。所得到的氨基甲酸酯、硫代氨基甲酸酯或脲非常有用，尤其是作为农药。

  公开号：

  US04725680A1

文献信息

• Procédé de préparation de dérivés de l'acide carbamique
  申请人：SOCIETE NATIONALE DES POUDRES ET EXPLOSIFS

  公开号：EP0155862B1

  公开（公告）日：1987-07-22
• US4725680A
  申请人：——

  公开号：US4725680A

  公开（公告）日：1988-02-16
• Process for the preparation of carbamates, thiocarbamates and ureas
  申请人：Societe Nationale des Poudres et Explosifs

  公开号：US04725680A1

  公开（公告）日：1988-02-16

  The invention relates to a process for preparing carbamic acid derivatives of formula: ##STR1## in which R.sup.1 or R.sup.2 denotes a hydrogen atom or a substituted or unsubstituted, saturated or unsaturated aliphatic, cycloaliphatic or heterocyclic radical, or R.sup.1 and R.sup.2 together form a ring, and Y denotes OR, SR, ##STR2## groups, R being a substituted or unsubstituted, saturated or unsaturated aliphatic or cycloaliphatic radical, or a substituted or unsubstituted aromatic radical, R.sup.3 and R.sup.4 denote a hydrogen atom or an aliphatic, cycloaliphatic, araliphatic, aromatic or heterocyclic radical or together form a ring, and R.sup.6 and R.sup.7 denote a saturated or unsaturated, substituted or unsubstituted aliphatic or cycloaliphatic radical, a hydrogen atom, an alkylthio radical or an alkyloxy radical. According to the process, a compound of formula ##STR3## is reacted with an .alpha.-halogenated derivative of formula ##STR4## at a temperature of -5.degree. to 150.degree. C. in the presence of an acceptor for hydrohalic acid. The carbamates, thiocarbamates or ureas obtained are very useful, especially as pesticides.

  本发明涉及一种制备公式为##STR1##的氨基甲酸衍生物的方法，其中R.sup.1或R.sup.2表示氢原子或取代或未取代的、饱和或不饱和的脂肪族、环脂肪族或杂环基团，或者R.sup.1和R.sup.2共同形成一个环，Y表示OR、SR、##STR2##基团，R表示取代或未取代的、饱和或不饱和的脂肪族或环脂肪族基团，或者取代或未取代的芳香族基团，R.sup.3和R.sup.4表示氢原子或脂肪族、环脂肪族、脂环族、芳香族或杂环基团，或者共同形成一个环，R.sup.6和R.sup.7表示饱和或不饱和的、取代或未取代的脂肪族或环脂肪族基团、氢原子、烷基硫基团或烷氧基团。根据本过程，将公式为##STR3##的化合物与公式为##STR4##的α-卤代衍生物在-5至150摄氏度的温度下，在卤化氢酸的受体存在下进行反应。所得到的氨基甲酸酯、硫代氨基甲酸酯或脲非常有用，尤其是作为农药。
• The Design of Agents To Control DNA Methylation Adducts. Enhanced Major Groove Methylation of DNA by an <i>N</i>-Methyl-<i>N</i>-nitrosourea Functionalized Phenyl Neutral Red Intercalator
  作者：Pratibha Mehta、Kevin Church、Jonathan Williams、Fa-Xian Chen、Lance Encell、David E. G. Shuker、Barry Gold

  DOI：10.1021/tx960007n

  日期：1996.1.1

  An N-methyl-N-nitrosourea (MNU) moiety [CH3N(N=O)C(=O)NH-] linked to the C4'-position of the 5-substituted phenyl ring of phenyl neutral red (PNR), 2-methyl-3-amino-5-[p-[[2-[(N-nitroso-N-methylcarbamoyl)amino]ethyl]carbamoyl]phenyl]-7-(dimethylamino)phenazenium chloride (MNU-PNR), has been synthesized as an approach to design a molecule that will deliver alkylating agents with some preference to guanine (Gua) in the major groove of DNA. The PNR nucleus was chosen because previous studies suggested the following: (1) PNR binds with a slight preference for G/C rich sequences; and (2) PNR intercalates into DNA from the major groove with the 5-phenyl ring pointing out into the major groove (Muller, W., Bunemann, H., and Dattagupta, N. (1975) fur. J. Biochem. 54, 279-291). It is demonstrated that MNU-PNR yields 2.6 and 6.0 times more N7-methylguanine (7-MeGua) than MNU at low salt (10 mM Tris buffer) and high salt (10 mM Tris buffer + 200 mM NaCl), respectively. It is also shown that the ratio of 7-MeGua (a major groove adduct) to N3-methyladenine (a minor groove adduct) is approximately 5 times higher for MNU-PNR than for MNU. The yield of the 7-MeGua adduct is decreased by the coaddition of a nonmethylating analogue of MNU-PNR or NaCl, but increased in the presence of the minor groove intercalator, ethidium bromide. Using a P-32-end-labeled restriction fragment, the enhanced methylation by MNU-PNR at 7-Gua is confirmed, and it is demonstrated that the sequence-dependent formation of 7-MeGua from MNU-PNR is the same as that seen with MNU. UV, circular dichroism, and viscosity studies are consistent with MNU-PNR binding to DNA via an intercalation-based process.