1-[(Diethylphosphono)methyl]-(4,5-dihydro)thiazole | 149770-58-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: 1-[(Diethylphosphono)methyl]-(4,5-dihydro)thiazole
• 英文别名: 2-(Diethoxyphosphorylmethyl)-4,5-dihydro-1,3-thiazole
• CAS: 149770-58-1
• 化学式: C₈H₁₆NO₃PS
• 分子量: 237.26
• InChiKey: DHZIDXXDUOEMDQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  73.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  糠醛 、 1-[(Diethylphosphono)methyl]-(4,5-dihydro)thiazole 在 sodium hydride 作用下， 生成 2-(2-(2-furyl)vinyl)-4,5-dihydrothiazole
  参考文献：
  名称：

  Synthèse, activités anti-parasitaire et anti-fongique d'arylalkyl- et d'arylvinylthiazolines

  摘要：

  Twenty-seven arylalkyl- or arylvinylthiazolines were synthesized and tested in vitro against three genera of nematodes, various yeasts and opportunistic fungi. Vinyl compounds seem to have an interesting filaricidal activity against Molinema dessetae and anti-fungal activity against yeasts.

  DOI：

  10.1016/0223-5234(93)90076-q
• 作为产物：
  描述：

  2-diethoxyphosphoryl-N-(2-hydroxyethyl)ethanethioamide 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以51%的产率得到1-[(Diethylphosphono)methyl]-(4,5-dihydro)thiazole
  参考文献：
  名称：

  新型不对称膦酰化噻唑啉的合成及其在烯烃化反应中的应用

  摘要：

  N-(2-羟基烷基)-2-磷酸乙硫酰胺由易得的磷酸二硫乙酸酯和商业化的手性β-氨基醇制备而成。利用同一分子中羟基（亲核试剂）和C=S（亲电试剂）的共存，我们通过Mitsunobu反应的分子内环化获得了新的手性磷酸化噻唑啉。随后，这些噻唑啉-磷酸酯参与了霍纳-瓦茨沃斯-埃蒙斯反应，生成不对称的烯基噻唑啉。

  DOI：

  10.1055/s-2000-6324

文献信息

• Bis-Cationic Heteroaromatics as Macrofilaricides:  Synthesis of Bis-Amidine and Bis<i>-</i>Guanylhydrazone Derivatives of Substituted Imidazo[1,2-<i>a</i>]pyridines
  作者：Richard J. Sundberg、Sujay Biswas、Krishna Kumar Murthi、Donna Rowe、John W. McCall、Michael T. Dzimianski

  DOI：10.1021/jm9803368

  日期：1998.10.1

  A series of guanylhydrazone, amidine, and hydrazone derivatives of 2-phenylimidazo[1,2-a]pyridine have been prepared and evaluated for macrofilarial activity against Acanthocheilonema viteae and Brugia pahangi in jirds. Compounds with 4',6-bis-substitution by cyclic guanylhydrazone groups show activity. 4',6-Bis-amidines show some activity but are more toxic; 4'- or 6-monosubstituted compounds are inactive. 2,6-Bis-substituted compounds lacking the phenyl ring are inactive. 4',6-Bis-substituted compounds having additional double bonds inserted between the heterocyclic ring and the phenyl ring or between the substituent and the ring system show reduced activity.
• Synthèse, activités anti-parasitaire et anti-fongique d'arylalkyl- et d'arylvinylthiazolines
  作者：R Caujolle、G Baziard-Mouysset、JD Favrot、M Payard、PR Loiseau、H Amarouch、MD Linas、JP Seguela、PM Loiseau、C Bories、P Gayral

  DOI：10.1016/0223-5234(93)90076-q

  日期：1993.1

  Twenty-seven arylalkyl- or arylvinylthiazolines were synthesized and tested in vitro against three genera of nematodes, various yeasts and opportunistic fungi. Vinyl compounds seem to have an interesting filaricidal activity against Molinema dessetae and anti-fungal activity against yeasts.
• Synthesis of New Asymmetric Phosphonylated Thiazolines and their Use in Olefination Reactions
  作者：Nicolas Leflemme、Patrice Marchand、Mihaela Gulea、Serge Masson

  DOI：10.1055/s-2000-6324

  日期：——

  N-(2-Hydroxyalkyl)-2-phosphonoethanethioamides were prepared from a readily accessible phosphonodithioacetate and commercial chiral β-amino alcohols. Taking advantage of both the presence of the hydroxy group (nucleofuge) and of the C=S (nucleophile) in the same molecule, we obtained new chiral phosphonylated thiazolines by an intramolecular cyclisation using the Mitsunobu procedure. These thiazoline-phosphonates were then involved in Horner-Wadsworth-Emmons reaction to give asymmetric vinylic thiazolines.

  N-(2-羟基烷基)-2-磷酸乙硫酰胺由易得的磷酸二硫乙酸酯和商业化的手性β-氨基醇制备而成。利用同一分子中羟基（亲核试剂）和C=S（亲电试剂）的共存，我们通过Mitsunobu反应的分子内环化获得了新的手性磷酸化噻唑啉。随后，这些噻唑啉-磷酸酯参与了霍纳-瓦茨沃斯-埃蒙斯反应，生成不对称的烯基噻唑啉。