2-benzoylamino-1-cyano-2-thioxoethylidenetriphenylphosphorane | 155786-93-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-benzoylamino-1-cyano-2-thioxoethylidenetriphenylphosphorane
• 英文别名: N-(2-Cyano-2-(triphenylphosphoranylidene)ethanethioyl)benzamide；N-[2-cyano-2-(triphenyl-λ5-phosphanylidene)ethanethioyl]benzamide
• CAS: 155786-93-9
• 化学式: C₂₈H₂₁N₂OPS
• 分子量: 464.527
• InChiKey: NGQLNYJGSCPBQM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  85
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-benzoylamino-1-cyano-2-thioxoethylidenetriphenylphosphorane 在 硫酸 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 3.0h， 生成 (6-Benzylsulfanyl-4-oxo-2-phenyl-1,4-dihydro-pyrimidin-5-yl)-triphenyl-phosphonium; chloride
  参考文献：
  名称：

  Syntheses of Functionalized Pyrimidines from the Products of Addition of Triphenylphosphoranylideneacetonitrile to Acyl Isothiocyanates

  摘要：

  The products of addition of accessible phosphorus-containing ylide Ph3P-CHCN to acyl and alkoxycarbonyl isocyanates readily cyclize under the action of methanolic HCl. This reaction was used for preparing a broad range of new 5-phosphonium derivatives of di- and trifunctionalized pyrimidine bases. Among them, the corresponding tertiary phosphonium salts containing no labile hydrogen atoms are especially important. Under mild conditions, they undergo dephosphorylation in the presence of alkalis to give 4-mercapto, 4,6-dimercapto-, and 2,4,6-trimercaptopyrimidine derivatives which are difficult or impossible to prepare by traditional routes.

  DOI：

  10.1023/b:rugc.0000045875.40116.eb
• 作为产物：
  描述：

  苯甲酰基异硫氰酸酯 、 (三苯基膦)乙腈 以 乙腈 为溶剂， 反应 3.0h， 以70%的产率得到2-benzoylamino-1-cyano-2-thioxoethylidenetriphenylphosphorane
  参考文献：
  名称：

  具有挑战性的嘧啶系列叶立德甜菜碱合成方法

  摘要：

  可用的内鎓盐-C̄HCN与酰基异氰酸酯及其硫代类似物的加合物进行易环化，在甲醇中由氯化氢促进，得到高产率的2-烷基（芳基）-4-羟基（巯基）-6-氧代-1,6 -二氢嘧啶-5-基-三苯基-氯化物适用于制备嘧啶系列的几种类型的内酯-甜菜碱，其结构通过化学转化和X射线衍射分析确定。尽管这些杂环亲核试剂具有介观特性，但它们仍以区域选择性方式烷基化，这证明该方法对于合成非磷酸化嘧啶衍生物非常重要，否则很难获得。

  DOI：

  10.1016/0040-4020(96)00425-5

文献信息

• A challenging synthetic approach to phosphonium ylide-betaines of the pyrimidine series
  作者：Luc Van Meervelt、Oleg B. Smolii、Nikolai I. Mishchenko、Dmitrii B. Shakhnin、Evgenii A. Romanenko、Boris S. Drach

  DOI：10.1016/0040-4020(96)00425-5

  日期：1996.6

  several types of phosphonium ylide-betaines of the pyrimidine series, the structure of which was established by chemical transformations and X-ray diffraction analysis. Despite the mesomeric character of these heterocyclic nucleophilic agents, they are alkylated in a regioselective manner, which proves this approach to be important for the synthesis of non-phosphorylated pyrimidine derivatives, which

  可用的内鎓盐-C̄HCN与酰基异氰酸酯及其硫代类似物的加合物进行易环化，在甲醇中由氯化氢促进，得到高产率的2-烷基（芳基）-4-羟基（巯基）-6-氧代-1,6 -二氢嘧啶-5-基-三苯基-氯化物适用于制备嘧啶系列的几种类型的内酯-甜菜碱，其结构通过化学转化和X射线衍射分析确定。尽管这些杂环亲核试剂具有介观特性，但它们仍以区域选择性方式烷基化，这证明该方法对于合成非磷酸化嘧啶衍生物非常重要，否则很难获得。
• Smolii, O. B.; Panchishin, S. Ya.; Drach, B. S., Russian Journal of General Chemistry, 1993, vol. 63, # 9.1, p. 1390 - 1393
  作者：Smolii, O. B.、Panchishin, S. Ya.、Drach, B. S.

  DOI：——

  日期：——
• Syntheses of Functionalized Pyrimidines from the Products of Addition of Triphenylphosphoranylideneacetonitrile to Acyl Isothiocyanates
  作者：L. V. Muzychka、O. B. Smolii、B. S. Drach

  DOI：10.1023/b:rugc.0000045875.40116.eb

  日期：2004.7

  The products of addition of accessible phosphorus-containing ylide Ph3P-CHCN to acyl and alkoxycarbonyl isocyanates readily cyclize under the action of methanolic HCl. This reaction was used for preparing a broad range of new 5-phosphonium derivatives of di- and trifunctionalized pyrimidine bases. Among them, the corresponding tertiary phosphonium salts containing no labile hydrogen atoms are especially important. Under mild conditions, they undergo dephosphorylation in the presence of alkalis to give 4-mercapto, 4,6-dimercapto-, and 2,4,6-trimercaptopyrimidine derivatives which are difficult or impossible to prepare by traditional routes.