phthalimidoacetyl isothiocyanate | 1283593-17-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: phthalimidoacetyl isothiocyanate
• CAS: 1283593-17-8
• 化学式: C₁₁H₆N₂O₃S
• 分子量: 246.246
• InChiKey: IABCVSPZKGTADN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.91
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  66.81
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  phthalimidoacetyl isothiocyanate 、 丙酮苯腙 以 丙酮 为溶剂， 以85%的产率得到2-((2,2-dimethyl-4-phenyl-5-thioxo-2,3,4,5-tetrahydro-1,3,4,6-oxatriazepin-7-yl)methyl)isoindoline-1,3-dione
  参考文献：
  名称：

  Utility of Phthalimidoacyl Isothiocyanate in Synthesis of Quinazolines, Benzoxazoles, Benzimidazoles, 1,2,4-Triazoles, and Oxatriazepines

  摘要：

  Phthalimidoacyl isothiocyanates 1a,b participated in a wide range of addition-cyclization reactions. Simultaneous or subsequent cyclization of the obtained adducts gave derivatives of quinazoline, benzoxazole, benzimidazole, 1,2,4-triazole, and oxatriazepine. The structures of all the products were confirmed by microanalytical and spectroscopic data.

  DOI：

  10.1080/10426507.2011.597804
• 作为产物：
  描述：

  硫氰酸铵 、 N-邻苯二甲酰甘氨酰氯 反应 0.5h， 生成 phthalimidoacetyl isothiocyanate
  参考文献：
  名称：

  Utility of Phthalimidoacyl Isothiocyanate in Synthesis of Quinazolines, Benzoxazoles, Benzimidazoles, 1,2,4-Triazoles, and Oxatriazepines

  摘要：

  Phthalimidoacyl isothiocyanates 1a,b participated in a wide range of addition-cyclization reactions. Simultaneous or subsequent cyclization of the obtained adducts gave derivatives of quinazoline, benzoxazole, benzimidazole, 1,2,4-triazole, and oxatriazepine. The structures of all the products were confirmed by microanalytical and spectroscopic data.

  DOI：

  10.1080/10426507.2011.597804

文献信息

• The Reformatsky analogous reaction for the synthesis of novel β-thioxoesters <i>via</i> using aroyl isothiocyanates under solvent-free ball milling and conventional conditions
  作者：Paula S. Farag、Magdy M. Hemdan、Aya I. Hassaballah

  DOI：10.1039/d2ra01154a

  日期：——

  The classical Reformatsky reaction, initially described in 1887, is considered one of the most useful ways of forming C–C bonds. The target of this work includes improving the Reformatsky reaction between aroyl isothiocyanates and α-haloesters using metallic zinc to form β-thioxoesters (3–11). In this procedure, a new metal-mediated carbon–carbon linkage is formed with the formation of an organozinc

  最初于 1887 年描述的经典 Reformatsky 反应被认为是形成 C-C 键的最有用的方法之一。这项工作的目标包括改进芳酰基异硫氰酸酯和 α-卤代酯之间的 Reformatsky 反应，使用金属锌形成 β-硫代酯 (3-11)。在此过程中，形成了新的金属介导的碳-碳键，形成有机锌卤化物并由于稀酸的存在而分解，通过常规技术和球磨提供所需产物的良好收率。Reformatsky 反应不需要溶剂和惰性气体。
• Synthesis, Insecticidal Activity and DFT Study of 1,2,4-Triazolidinthione, 1,3,5-Oxadiazine and Thiourea Derivatives
  作者：Amira A. El-Sayed、Galal A. Elsayed、Sameh A. Rizk、Mahmoud F. Ismail

  DOI：10.1080/00304948.2023.2209489

  日期：2024.1.2

  Published in Organic Preparations and Procedures International: The New Journal for Organic Synthesis (Vol. 56, No. 1, 2024)

  发表于《国际有机制备和程序：有机合成新期刊》（第 56 卷，第 1 期，2024 年）