(S)-methyl 2-((R)-2-((tert-butoxycarbonyl)amino)-3-((4-methoxybenzoyl)thio)propanamido)propanoate | 1422008-15-8

• 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: (S)-methyl 2-((R)-2-((tert-butoxycarbonyl)amino)-3-((4-methoxybenzoyl)thio)propanamido)propanoate
• 英文别名: Boc-Cys(Bz(4-OMe))-Ala-OMe；methyl (2S)-2-[[(2R)-3-(4-methoxybenzoyl)sulfanyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]propanoate
• CAS: 1422008-15-8
• 化学式: C₂₀H₂₈N₂O₇S
• 分子量: 440.518
• InChiKey: OSLGFNIBMXRDOP-WFASDCNBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  30
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  145
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  4-碘苯甲醚 、 9-methyl-9H-fluorene-9-carbonyl chloride 、 Boc-Cys-Ala-OMe 在 N-甲基二环己基胺 、 sodium acetate 、 palladium diacetate 、 双(2-二苯基磷苯基)醚 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 、 tri tert-butylphosphoniumtetrafluoroborate 作用下， 以 乙二醇二甲醚 为溶剂， 反应 18.0h， 以71%的产率得到(S)-methyl 2-((R)-2-((tert-butoxycarbonyl)amino)-3-((4-methoxybenzoyl)thio)propanamido)propanoate
  参考文献：
  名称：

  Pd-Catalyzed Thiocarbonylation with Stoichiometric Carbon Monoxide: Scope and Applications

  摘要：

  A general protocol for the Pd-catalyzed thiocarbonylation of aryl iodides with stoichiometric carbon monoxide has been established employing a catalytic system composed of Pd(OAc)(2) and DPEphos with low catalyst loading (1 mol %). Both electron-rich and -deficient aryl iodides proved effective for these couplings with aryl and alkyl thiols. The choice of the metal ligands and the solvent system was crucial for the efficiency and chemoselectivity of these transformations.

  DOI：

  10.1021/ol400138m

文献信息

• Palladium-Catalyzed Thiocarbonylation of Aryl, Vinyl, and Benzyl Bromides
  作者：Mia N. Burhardt、Andreas Ahlburg、Troels Skrydstrup

  DOI：10.1021/jo5009965

  日期：2014.12.19

  A catalytic protocol for synthesis of thioesters from aryl, vinyl, and benzyl bromides as well as benzyl chlorides was developed using only stoichiometric amounts of carbon monoxide, produced from a solid CO precursor inside a two-chamber system. As a catalytic system, the combination of bis(benzonitrile) palladium(II) chloride and Xantphos furnished the highest yields of the desired compounds, along

  使用芳烃，乙烯基和苄基溴化物以及苄基氯来合成硫酯的催化方案仅使用化学计量量的一氧化碳开发，该一氧化碳是由两室系统中的固态CO前驱体产生的。作为催化体系，双（苄腈）氯化钯（II）和Xantphos的组合在120°C的苯甲醚溶液中提供了所需化合物以及弱碱NaOAc的最高收率。为了确保反应中的高化学选择性，催化体系和溶剂的选择被证明是重要的。富电子和缺电子的芳基溴在此反应中均能很好地发挥作用。向反应中加入1当量的碘化钠可改善缺电子的芳基溴化物的化学选择性。硫醇范围包括芳基和烷基硫醇，包括2-巯基二苯甲酮，其中通过硫羰基化和随后的McMurry偶联生成不同取代的苯并噻吩。事实证明，该方法可以适用于13 C引入噻吩环。
• Pd-Catalyzed Thiocarbonylation with Stoichiometric Carbon Monoxide: Scope and Applications
  作者：Mia N. Burhardt、Rolf H. Taaning、Troels Skrydstrup

  DOI：10.1021/ol400138m

  日期：2013.2.15

  A general protocol for the Pd-catalyzed thiocarbonylation of aryl iodides with stoichiometric carbon monoxide has been established employing a catalytic system composed of Pd(OAc)(2) and DPEphos with low catalyst loading (1 mol %). Both electron-rich and -deficient aryl iodides proved effective for these couplings with aryl and alkyl thiols. The choice of the metal ligands and the solvent system was crucial for the efficiency and chemoselectivity of these transformations.