4-chloro-2-phenyl-thiazole-5-carbaldehyde | 108263-77-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-chloro-2-phenyl-thiazole-5-carbaldehyde
• 英文别名: 4-Chloro-2-phenylthiazole-5-carbaldehyde；4-chloro-2-phenyl-1,3-thiazole-5-carbaldehyde
• CAS: 108263-77-0
• 化学式: C₁₀H₆ClNOS
• 分子量: 223.683
• InChiKey: BEXKFRZZFNJNSZ-UHFFFAOYSA-N

物化性质

• 沸点：
  378.5±45.0 °C(Predicted)
• 密度：
  1.388±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• 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

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2934100090

反应信息

• 作为反应物：
  描述：

  4-chloro-2-phenyl-thiazole-5-carbaldehyde 在 sodium azide 、 溶剂黄146 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 18.0h， 生成 5-<(N-p-tolylimino)methyl>-2-phenyl-4-<(triphenylphosphoranylidene)amino>thiazole
  参考文献：
  名称：

  Fused pyrimidines by a tandem aza-Wittig/electrocyclic ring closure strategy: synthesis of pyrazolo[3,4-d]pyrimidine, [1,2,3]triazolo[4,5-d]pyrimidine, and thiazolo[4,5-d]pyrimidine derivatives

  摘要：

  DOI：

  10.1021/jo00255a003

文献信息

• Neighbouring group effects on rates of thermolysis of 4-azidothiazoles
  作者：Erik Ceulemans、Karin Vercauteren、Leonard K. Dyall、Dirk Buelens、Wim Dehaen

  DOI：10.1016/s0040-4020(97)00638-8

  日期：1997.7

  Rate measurements for thermolysis of 4-azidothiazoles in p-xylene solution have identified neighbouring group effects from nitro (19-fold rate increase), phenyliminomethyl (16), formyl (4.5) and acetyl (2.2) substituents in the 5-position. These effects are very similar in magnitude to those measured for 3-azidothiophenes, whereas in azidobenzenes the rate increases are much larger, 5-Substituents in 4-azidothiazole which are capable of conjugative donation (phenyl, ethyl propenoate) also increased the reaction rate. The reactions involving neighbouring group participation led to cyclized products from the 4-azidothiazoles though not all of these products were stable under the thermolysis conditions. (C) 1997 Elsevier Science Ltd.
• Diastereoselective intramolecular hetero Diels–Alder approach towards polycyclic heterocycles
  作者：Erik Ceulemans、Marieke Voets、Sabine Emmers、Koen Uytterhoeven、Luc Van Meervelt、Wim Dehaen

  DOI：10.1016/s0040-4020(01)01153-x

  日期：2002.1

  Several different heterocyclic aldehydes, derived from pyrazole. pyrimidine, pyridine, indole and thiazole, were converted to polyheterocyclic compounds containing four to seven rings. The key steps in the sequence were a Knoevenagel condensation of the aldehyde and a heterocyclic carbonyl compound, such as pyrazolone and isoxazolone, followed by an intramolecular hetero Diets-Alder reaction. Most final products were isolated with high yield and diastereoselecivity. The isoxazolo fused cycloadducts formed interesting spiro-adducts upon heating. The cis nature of the bridging hydrogens of the heterocycles was evidenced by X-ray diffraction analysis.(dagger) (C) 2002 Elsevier Science Ltd. All rights reserved.
• MOLINA, PEDRO;ARQUES, ANTONIO;VINADER, MARIA VICTORIA;BECHER, JAN;BRONDUM+, J. ORG. CHEM., 53,(1988) N 20, C. 4654-4663
  作者：MOLINA, PEDRO、ARQUES, ANTONIO、VINADER, MARIA VICTORIA、BECHER, JAN、BRONDUM+

  DOI：——

  日期：——