1-(2-thiazolyl)propynone | 271597-73-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2-thiazolyl)propynone
• 英文别名: 1-(1,3-Thiazol-2-yl)prop-2-yn-1-one
• CAS: 271597-73-0
• 化学式: C₆H₃NOS
• 分子量: 137.162
• InChiKey: WGXQDWKDGQZGEG-UHFFFAOYSA-N

物化性质

• 沸点：
  245.6±23.0 °C(Predicted)
• 密度：
  1.319±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  58.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 3-amino-3-(2-thienyl)-2-propenoate 、 1-(2-thiazolyl)propynone 以 乙醇 为溶剂， 反应 1.0h， 以70%的产率得到ethyl 6-(thiazol-2-yl)-2-(thien-2-yl)pyridine-3-carboxylate
  参考文献：
  名称：

  Total Synthesis of the Thiopeptide Promothiocin A

  摘要：

  The thiopeptide (or thiostrepton) antibiotics are a class of sulfur-containing highly modified cyclic peptides with interesting biological activity. Described herein is the total synthesis of the thiopeptide antibiotic promothiocin A, which utilizes a modified Bohlmann-Rahtz pyridine synthesis to establish the oxazolyl-thiazole-pyridine heterocyclic centerpiece of the antibiotic. The oxazole building blocks were obtained by a dirhodium(II)-catalyzed chemoselective carbenoid N-H insertion reaction followed by cyclodehydration, and the thiazoles by the Hantzsch reaction. Two different strategies for macrocyclization were successfully employed, with the dehydroalanine side chain of the natural product being introduced in the last steps of the synthesis.

  DOI：

  10.1021/ja994247b
• 作为产物：
  描述：

  1-(1,3-噻唑-2-基)-2-丙炔-1-醇 在 manganese(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 1-(2-thiazolyl)propynone
  参考文献：
  名称：

  钌和O的磷环稠合双环金属呋喃配合物

  摘要：

  由末端酮HC≡C（C = O）R与顺式-[Ru / Os（dppm）2 Cl 2]（dppm = 1,1-双（二苯基膦基）甲烷）。人们发现，涉及金属-亚乙烯基的途径是这些络合物在能量上可行的形成机理。像许多metal功能化的药物一样，这些含phospho的金属呋喃也具有诱导线粒体功能障碍的能力。与它们的金属前体和经典的抗癌药顺铂相比，它们还对几种人类癌细胞系表现出更强的细胞毒性。总体而言，这项工作通过Ru II和Os II中心激活炔烃，为功能性金属环的合理设计提供了结构和机理方面的见解。

  DOI：

  10.1002/chem.201901080

文献信息

• Phosphonium‐Ring‐Fused Bicyclic Metallafuran Complexes of Ruthenium and Osmium
  作者：Chi‐Fung Yeung、Lai‐Hon Chung、Sze‐Wing Ng、Hau‐Lam Shek、Sheung‐Ying Tse、Siu‐Chung Chan、Man‐Kit Tse、Shek‐Man Yiu、Chun‐Yuen Wong

  DOI：10.1002/chem.201901080

  日期：2019.7.11

  Metallafuran complexes with a fused five‐membered phosphonium ring were synthesized from reactions between terminal ynones HC≡C(C=O)R and cis‐[Ru/Os(dppm)2Cl2] (dppm=1,1‐bis(diphenylphosphino)methane). A metal–vinylidene‐involving pathway was found to be an energetically feasible formation mechanism for these complexes. These phosphonium‐containing metallafurans, like many phosphonium‐functionalized

  由末端酮HC≡C（C = O）R与顺式-[Ru / Os（dppm）2 Cl 2]（dppm = 1,1-双（二苯基膦基）甲烷）。人们发现，涉及金属-亚乙烯基的途径是这些络合物在能量上可行的形成机理。像许多metal功能化的药物一样，这些含phospho的金属呋喃也具有诱导线粒体功能障碍的能力。与它们的金属前体和经典的抗癌药顺铂相比，它们还对几种人类癌细胞系表现出更强的细胞毒性。总体而言，这项工作通过Ru II和Os II中心激活炔烃，为功能性金属环的合理设计提供了结构和机理方面的见解。
• Total Synthesis of the Thiopeptide Promothiocin A
  作者：Mark C. Bagley、Katherine E. Bashford、Claire L. Hesketh、Christopher J. Moody

  DOI：10.1021/ja994247b

  日期：2000.4.1

  The thiopeptide (or thiostrepton) antibiotics are a class of sulfur-containing highly modified cyclic peptides with interesting biological activity. Described herein is the total synthesis of the thiopeptide antibiotic promothiocin A, which utilizes a modified Bohlmann-Rahtz pyridine synthesis to establish the oxazolyl-thiazole-pyridine heterocyclic centerpiece of the antibiotic. The oxazole building blocks were obtained by a dirhodium(II)-catalyzed chemoselective carbenoid N-H insertion reaction followed by cyclodehydration, and the thiazoles by the Hantzsch reaction. Two different strategies for macrocyclization were successfully employed, with the dehydroalanine side chain of the natural product being introduced in the last steps of the synthesis.