2-isothiocyanatoacetic acid benzyl ester | 1226977-53-2

• 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-isothiocyanatoacetic acid benzyl ester
• 英文别名: 2-isothiocyanoethanoic acid benzyl ester；isothiocyanoethanoic acid benzyl ester；Benzyl 2-isothiocyanatoacetate
• CAS: 1226977-53-2
• 化学式: C₁₀H₉NO₂S
• 分子量: 207.253
• InChiKey: YUSGZQMGRRZUSO-UHFFFAOYSA-N

物化性质

• 沸点：
  325.2±25.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  70.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-isothiocyanatoacetic acid benzyl ester 在 碘乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 benzyl N-(1H-benzimidazol-2-yl)glycinate
  参考文献：
  名称：

  Iodoacetic Acid is an Efficient Reagent for the Synthesis of Amino Acid Derived 2-Aminobenzimidazoles

  摘要：

  Chiral, nonracemic, N-unprotected amino acids were converted into the corresponding N-benzimidazol-2-yl derivatives by a sequential procedure involving initial formation of isothiocyanates, their reaction with arene-1,2-diamines, and cyclization-desulfurization of the intermediate thioureas with iodoacetic acid. The simplified workup and the lack of volatile or toxic byproducts in the key desulfurization step renders iodoacetic acid a superior reagent to the usual reagent, iodomethane.

  DOI：

  10.1055/s-0032-1316849
• 作为产物：
  描述：

  硫光气 、 甘氨酸苄酯盐酸盐 在 碳酸氢钠 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 0.92h， 生成 2-isothiocyanatoacetic acid benzyl ester
  参考文献：
  名称：

  Iodoacetic Acid is an Efficient Reagent for the Synthesis of Amino Acid Derived 2-Aminobenzimidazoles

  摘要：

  Chiral, nonracemic, N-unprotected amino acids were converted into the corresponding N-benzimidazol-2-yl derivatives by a sequential procedure involving initial formation of isothiocyanates, their reaction with arene-1,2-diamines, and cyclization-desulfurization of the intermediate thioureas with iodoacetic acid. The simplified workup and the lack of volatile or toxic byproducts in the key desulfurization step renders iodoacetic acid a superior reagent to the usual reagent, iodomethane.

  DOI：

  10.1055/s-0032-1316849

文献信息

• Synthesis of N-urethane protected amino alkyl (S-methyl)-isothiouronium compounds and carbodiimide tethered peptidomimetics: an application for guanidino and substituted guanidino peptidomimetics synthesis
  作者：Basavaprabhu Hosamani、N. Narendra、Girish Prabhu、Vommina V. Sureshbabu

  DOI：10.1039/c4ra07252a

  日期：——

  The synthesis of N,N′-disubstituted and N,N′,N′′-trisubstituted guanidine linked peptidomimetic molecules suitably decorated in the peptide backbone has been delineated. Nα-Protected amino acid derived S-methyl isothiouronium derivatives are employed as the key intermediates for the synthesis of guanidinopeptide mimics. Synthesis of a new class of carbodiimide tethered dipeptidomimetics has also been outlined wherein a Staudinger-aza-Wittig type reaction between amino alkyl azide and isothiocyanato esters is employed. Thus obtained carbodiimides have been demonstrated as starting materials for the construction of guanidino peptide mimics as well as an array of trisubstituted guanidine mimetics bearing N-hydroxy, cyano and amino function as third substitutions at the guanidino unit in the backbone.

  已阐明了合成N,N′-二取代和N,N′,N′′-三取代的胍基连接肽模仿分子，这些分子在肽骨架中进行了适当的装饰。采用Nα-保护的氨基酸衍生的S-甲基异硫脲盐衍生物作为合成胍基肽模仿物的关键中间体。还概述了一类新型的碳二亚胺连接的二肽模仿物的合成，其中采用氨基烷基叠氮化物与异硫氰酸酯之间的斯陶丁格-阿扎-维蒂格反应。因此获得的碳二亚胺已被证明是构建胍基肽模仿物的起始材料，以及一系列具有N-羟基、氰基和氨基作为胍基单元中第三取代基的三取代胍基模仿物。
• Access to <i>N</i>-Difluoromethyl Amides, (Thio)Carbamates, Ureas, and Formamides
  作者：Filip G. Zivkovic、Gina Wycich、Linhao Liu、Franziska Schoenebeck

  DOI：10.1021/jacs.3c13711

  日期：2024.1.17

  herein. The synthetic strategy relies on the initial synthesis and straightforward derivatization of N-CF2H carbamoyl fluorides, which were prepared through a desulfurization–fluorination of thioformamides (─NH─C(H)═S) coupled with carbonylation. The newly made N-CF2H carbonyl compounds proved to be highly robust and compatible with numerous chemical transformations and downstream derivatizations, underscoring

  本文报道了首次有效获得N-二氟甲基酰胺、氨基甲酸酯、硫代氨基甲酸酯、脲、甲酰胺及其衍生物。该合成策略依赖于N -CF 2 H氨基甲酰氟的初始合成和直接衍生化，其通过硫代甲酰胺（─NH─C(H)=S）的脱硫氟化与羰基化反应制备。新制备的N -CF 2 H 羰基化合物被证明具有高度鲁棒性，并且与多种化学转化和下游衍生化相容，强调了这种新颖基序作为复杂功能分子构建块的潜力。