methyl 2,5-diphenylthiazolecarboxylate | 133415-16-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: methyl 2,5-diphenylthiazolecarboxylate
• 英文别名: methyl 2,5-diphenylthiazole-4-carboxylate；Methyl 2,5-diphenyl-1,3-thiazole-4-carboxylate
• CAS: 133415-16-4
• 化学式: C₁₇H₁₃NO₂S
• 分子量: 295.362
• InChiKey: IFEPBOJDYIEBOU-UHFFFAOYSA-N

物化性质

• 熔点：
  90-91.5 °C(Solv: hexane (110-54-3))
• 沸点：
  483.6±47.0 °C(Predicted)
• 密度：
  1.227±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  67.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 2,5-diphenylthiazolecarboxylate 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 5.0h， 生成 2,5-diphenylthiazole-4-carboxylic acid hydrazide
  参考文献：
  名称：

  Synthesis of novel thiazoles bearing hydrazine, thiosemicarbazide, thiazole, and thiazolidinone moieties

  摘要：

  Thiazolecarboxylate esters (I) and (II) react with hydrazine hydrate to give the acid hydrazides (III) and (IV), which then react with KSCN and PhNCS to give high yields of the thiosemicarbazides (V) (VIII). Cyclocondensation of the thiosemicarbazide (V) with 3-phenyl-3-chloro-2-oxopropionic acid derivatives gives compounds with two thiazole moieties (IX)-(XIV). The reaction of the phenylthiosemicarbazides (VII) and (VIII) with chloroacetyl chloride and (or) chloroacetic acid affords the thiazolidinonethiazoles (XV) and (XVI).

  DOI：

  10.1007/bf00959725
• 作为产物：
  描述：

  methyl 2-phenyl-4,5-dihydrothiazole-4-carboxylate 在 silver(I) acetate 、 copper diacetate 、 palladium dichloride 、 三甲基乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 methyl 2,5-diphenylthiazolecarboxylate
  参考文献：
  名称：

  Pd(ii)-catalyzed direct C5-arylation of azole-4-carboxylates through double C–H bond cleavage

  摘要：

  首次实现了通过双C–H键断裂的铂催化直接C5-芳基化反应，将简单的未活化芳烃与azole-4-羧酸酯进行反应。该协议提供了一种简便的方法，获得了多种5-芳基取代的azole-4-羧酸衍生物，并具有良好的功能团耐受性。

  DOI：

  10.1039/c2cc00081d

文献信息

• Mechanism Selection for Regiocontrol in Base-Assisted, Palladium-Catalysed Direct CH Coupling with Halides: First Approach for Oxazole- and Thiazole-4-Carboxylates
  作者：Laure Théveau、Cécile Verrier、Pierrik Lassalas、Thibaut Martin、Georges Dupas、Olivier Querolle、Luc Van Hijfte、Francis Marsais、Christophe Hoarau

  DOI：10.1002/chem.201101615

  日期：2011.12.16

  Both base‐assisted non‐concerted metallation–deprotonation (nCMD) and concerted metallation–deprotonation (CMD) have been identified as two potent operating mechanisms in palladium‐catalysed direct CH coupling of oxazole and thiazole‐4‐carboxylate esters with halides through base‐ and solvent‐effect experiments. Novel C2‐ and C5‐selective CMD direct arylation procedures in oxazole‐ and thiazole‐4‐carboxylate

  两个基地辅助非一致金属化-去质子化（NCMD）和协同金属化-去质子化（CMD）已被确定为在钯催化的直接C上两个有效的操作机构通过与卤化物恶唑的耦合和噻唑-4-羧酸酯ħ碱和溶剂效应实验。然后通过控制电子和空间因素之间的平衡，设计了恶唑和噻唑-4-羧酸酯系列中新颖的C2和C5选择性CMD直接芳基化方法。值得注意的是，钯催化剂和底物之间的电荷相互作用被确定为控制选择性和减少CMD反应中空间因素的影响的参数。
• Direct C-2 Arylation of Alkyl 4-Thiazolecarboxylates: New Insights in Synthesis of Heterocyclic Core of Thiopeptide Antibiotics
  作者：Thibaut Martin、Cécile Verrier、Christophe Hoarau、Francis Marsais

  DOI：10.1021/ol801035c

  日期：2008.7.3

  The Pd(0)-catalyzed regioselective C-2 (hetero)arylation of tert-butyl 4-thiazolecarboxylate with a broad (hetero)aryl halide is reported, including the direct coupling of pyridinyl halides. The process has allowed the preparation of valuable 2-pyridynyl-4-thiazolecarboxylates which are components of the complex heterocyclic core of thiopeptides antibiotics. As a first application, a synthesis of a tert-butyl sulfomycinamate thio-analogue from tert-butyl 4-thiazolecarboxylate is here described through a three-step direct pyridinylation, halogenation, and Stille cross-coupling sequence.
• Synthesis of functionally substituted 5-phenylthiazoles
  作者：V. A. Mamedov、I. A. Nuretdinov、D. N. Sadkova

  DOI：10.1007/bf01184545

  日期：1990.12

  The reaction of esters and amides of 3-phenyl-3-chloro-2-oxopropionic acid with thioamides and thiourea gave new 5-phenylthiazoles.
• Fused Polycyclic Nitrogen-Containing Heterocycles: VIII. Friedel–Crafts Intramolecular Cyclization of 5-Phenylthiazole-4-carboxylic Acids—A New Route to Indeno[2,1-d]thiazoles
  作者：V. A. Mamedov、A. T. Gubaidullin、I. Z. Nurkhametova、I. A. Litvinov、Ya. A. Levin

  DOI：10.1023/b:rujo.0000036076.65278.fe

  日期：2004.4

  Friedel-Crafts intramolecular cyclization in the presence of polyphosphoric acid of 2-substituted 5-phenylthiazole-4-carboxylic acids, which are obtained by alkaline hydrolysis of the corresponding esters, leads to indeno[2,1-d]thiazoles. According to the X-ray diffraction data, packing of their molecules in crystal is determined mainly by intermolecular pi-pi contacts, regardless of the substituent nature.
• Aryl–aryl coupling via palladium-catalyzed C–P/C–H bond cleavage
  作者：Ziyuan Li、Haipin Zhou、Jinyi Xu、Xiaoming Wu、Hequan Yao

  DOI：10.1016/j.tet.2013.02.001

  日期：2013.4

  The first example of aryl-aryl coupling through palladium-catalyzed C-P/C-H bond cleavage with good functional group tolerance is disclosed. This work demonstrates the phosphines could be used as coupling partners in palladium-catalyzed aryl-aryl coupling. (C) 2013 Elsevier Ltd. All rights reserved.