5-propyl-oxazole-4-carboxylic acid ethyl ester | 41172-58-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-propyl-oxazole-4-carboxylic acid ethyl ester
• 英文别名: 5-Propyloxazol-4-carbonsaeureaethylester；Ethyl 5-propyl-1,3-oxazole-4-carboxylate
• CAS: 41172-58-1
• 化学式: C₉H₁₃NO₃
• 分子量: 183.207
• InChiKey: MGIFQJMFGCGBLF-UHFFFAOYSA-N

物化性质

• 沸点：
  274.8±28.0 °C(Predicted)
• 密度：
  1.082±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  52.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-propyl-oxazole-4-carboxylic acid ethyl ester 在 盐酸 作用下， 以 甲醇 为溶剂， 生成 2-amino-3-oxo-hexanoic acid ethyl ester
  参考文献：
  名称：

  新的方便的α-C-酰基氨基酸和α-氨基酮的合成方法。

  摘要：

  DOI：

  10.1021/jo00960a028
• 作为产物：
  描述：

  丁酸酐 、 异氰基乙酸乙酯 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 5-propyl-oxazole-4-carboxylic acid ethyl ester
  参考文献：
  名称：

  Lipophilic 5,6,7,8-tetrahydropterin substrates for phenylalanine hydroxylase (monkey brain), tryptophan hydroxylase (rat brain) and tyrosine hydroxylase (rat brain)

  摘要：

  DOI：

  10.1016/0223-5234(87)90265-0

文献信息

• Decarboxylative CH Cross-Coupling of Azoles
  作者：Fengzhi Zhang、Michael F. Greaney

  DOI：10.1002/anie.200906921

  日期：2010.4.1

  use of diverse oxazoles 2 as suitable substrates in cross‐coupling reactions with azole‐5‐carboxylic acids 1 under palladium catalysis in the presence of copper carbonate. The reaction is successful for the synthesis of a range of bis(azole)s, and has been applied to the convergent synthesis of challenging poly azoles (dcpe=bis(dicyclohexylphosphino)ethane, DMSO=dimethyl sulfoxide, M.S.=molecular sieves)

  d'Azole化合物：标题反应表明，在碳酸铜存在下，在钯催化下，与恶唑-5羧酸1交叉偶联反应中，可使用多种恶唑2作为合适的底物。该反应成功合成了一系列双（唑），并已用于聚合合成具有挑战性的聚唑（dcpe =双（二环己基膦基）乙烷，DMSO =二甲基亚砜，MS =分子筛）。
• Synthesis and Structure–Activity Relationship Study of Antimicrotubule Agents Phenylahistin Derivatives with a Didehydropiperazine-2,5-dione Structure
  作者：Yuri Yamazaki、Koji Tanaka、Benjamin Nicholson、Gordafaried Deyanat-Yazdi、Barbara Potts、Tomoko Yoshida、Akiko Oda、Takayoshi Kitagawa、Sumie Orikasa、Yoshiaki Kiso、Hiroyuki Yasui、Miki Akamatsu、Takumi Chinen、Takeo Usui、Yuki Shinozaki、Fumika Yakushiji、Brian R. Miller、Saskia Neuteboom、Michael Palladino、Kaneo Kanoh、George Kenneth Lloyd、Yoshio Hayashi

  DOI：10.1021/jm2009088

  日期：2012.2.9

  Plinabulin (11, NPI-2358) is a potent microtubule-targeting agent derived from the natural diketopiperazine "phenylahistin" (1) with a colchicine-like tubulin depolymerization activity. Compound 11 was recently developed as VDA and is now under phase II clinical trials as an anticancer drug. To develop more potent antimicrotubule and cytotoxic derivatives based on the didehydro-DKP skeleton, we performed further modification on the tert-butyl or phenyl groups of 11, and evaluated their cytotoxic and tubulin-binding activities. In the SAR study, we developed more potent derivatives 33 with 2,5-difluorophenyl and 50 with activity of 33 and 50 exhibited a lowest effective concentration The values of 33 and 50 were 5 and 10 times more potent than second-generation derivative with both vascular disrupting and a benzophenone in place of the phenyl group. The anti-HuVEC of 2 and 1 nM for microtubule depolymerization, respectively. that of CA-4, respectively. These derivatives could be a valuable cytotoxic activities.