2-(diethoxymethyl)thiazole-4-carboxamide | 170033-70-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(diethoxymethyl)thiazole-4-carboxamide
• 英文别名: 2-(Diethoxymethyl)-1,3-thiazole-4-carboxamide；2-(diethoxymethyl)-1,3-thiazole-4-carboxamide
• CAS: 170033-70-2
• 化学式: C₉H₁₄N₂O₃S
• 分子量: 230.288
• InChiKey: AEQYUQKAKKQEAK-UHFFFAOYSA-N

物化性质

• 熔点：
  112-114 °C
• 沸点：
  368.3±37.0 °C(predicted)
• 密度：
  1.233±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  103
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(diethoxymethyl)thiazole-4-carboxamide 在 吡啶 、 三氯氧磷 作用下， 反应 2.0h， 以83%的产率得到
  参考文献：
  名称：

  Synthesis of saramycetic acid

  摘要：

  The first reported synthesis of saramycetic acid, a degradation product of the complex thiopeptide antibiotic cyclothiazomycin, is achieved in nine steps and 11% overall yield from diethoxyacetonitrile by a strategy, which incorporates two Hantzsch thiazole syntheses using thioamides prepared from the corresponding nitriles without the use of gaseous H2S. The synthetic material was transformed to methyl saramycetate, which had spectroscopic Properties in excellent agreement with the literature data. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.07.111
• 作为产物：
  描述：

  2,2-二乙氧基乙酰胺 在 tetraphosphorus decasulfide 、 4 A molecular sieve 、 氨 作用下， 以 甲醇 、 乙醇 、 苯 为溶剂， 反应 25.67h， 生成 2-(diethoxymethyl)thiazole-4-carboxamide
  参考文献：
  名称：

  锌（II）的三氟甲磺酸盐控制的C-（2-噻唑基）硝酮的1,3-偶极环加成反应：在合成新型偶氮唑啉类似物的过程中的应用

  摘要：

  当在1当量的三氟甲磺酸锌存在下进行反应时，C-（2-噻唑基）硝酮与烯丙基醇之间的环加成反应具有完全的外切选择性。在微波辐射下，反应速率大大提高。手性双亲亲油的使用使得该方法学可用于合成迄今未知的对映体纯的C-核苷噻唑林的异恶唑烷基类似物。

  DOI：

  10.1021/jo051572a

文献信息

• Novel C-nucleoside analogs of 1,3-dioxolane: Synthesis of enantiomeric (2′R,4′S)- and (2′S,4′R)-2-[4-(hydroxymethyl)-1,3-dioxolan-2-yl]-1,3-thiazol-4-carboxamide
  作者：Yuejun Xiang、Quincy Teng、Chung K. Chu

  DOI：10.1016/0040-4039(95)00625-m

  日期：1995.5

  Novel C-nucleosides (2′R,4′S)-and (2′S,4′R)-2-[4-(hydroxymethyl)-1,3-dioxolan-2-yl]-1,3-thiazole-4-carboxamide have been synthesized from stereoselectively induced condensation of optically active triols (S or R) with a 1,3-thiazole-4-carboxamide derivative.

  新型C-核苷（2'R，4'S）-和（2'S，4'R）-2- [4-（羟甲基）-1,3-二氧戊环-2-基] -1,3-噻唑-4-羧酰胺是由旋光性三醇（S或R）与1，3-噻唑-4-羧酰胺衍生物的立体选择性诱导的缩合反应合成的。
• Synthesis of saramycetic acid
  作者：Christian Glover、Eleanor A. Merritt、Mark C. Bagley

  DOI：10.1016/j.tetlet.2007.07.111

  日期：2007.9

  The first reported synthesis of saramycetic acid, a degradation product of the complex thiopeptide antibiotic cyclothiazomycin, is achieved in nine steps and 11% overall yield from diethoxyacetonitrile by a strategy, which incorporates two Hantzsch thiazole syntheses using thioamides prepared from the corresponding nitriles without the use of gaseous H2S. The synthetic material was transformed to methyl saramycetate, which had spectroscopic Properties in excellent agreement with the literature data. (c) 2007 Elsevier Ltd. All rights reserved.
• Zinc(II) Triflate-Controlled 1,3-Dipolar Cycloadditions of <i>C</i>-(2-Thiazolyl)nitrones:  Application to the Synthesis of a Novel Isoxazolidinyl Analogue of Tiazofurin
  作者：Ugo Chiacchio、Antonio Rescifina、Maria G. Saita、Daniela Iannazzo、Giovanni Romeo、Juan A. Mates、Tomas Tejero、Pedro Merino

  DOI：10.1021/jo051572a

  日期：2005.10.1

  The cycloaddition reaction between C-(2-thiazolyl) nitrones and allylic alcohol takes place with complete exo selectivity when the reactions are carried out in the presence of 1 equiv of zinc triflate. The rate of the reaction is increased enormously under microwave irradiation. The use of a chiral dipolarophile allowed application of the methodology to the synthesis of a hitherto unknown enantiomerically

  当在1当量的三氟甲磺酸锌存在下进行反应时，C-（2-噻唑基）硝酮与烯丙基醇之间的环加成反应具有完全的外切选择性。在微波辐射下，反应速率大大提高。手性双亲亲油的使用使得该方法学可用于合成迄今未知的对映体纯的C-核苷噻唑林的异恶唑烷基类似物。