2-[3-(4-Chlorophenyl)-7-oxa-4-thia-1,2,9,11-tetrazatricyclo[6.4.0.02,6]dodeca-5,8-dien-11-yl]propanoic acid

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-[3-(4-Chlorophenyl)-7-oxa-4-thia-1,2,9,11-tetrazatricyclo[6.4.0.02,6]dodeca-5,8-dien-11-yl]propanoic acid
• 化学式: C₁₅H₁₅ClN₄O₃S
• 分子量: 366.828
• InChiKey: CFWUPDMIWGMGLB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  93.9
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  聚合甲醛 、 DL-丙氨酸 、 5-(4-chlorophenyl)-5H-[1,3]thiazolo[4,3-b][1,3,4]oxadiazol-2-amine 在 盐酸 作用下， 生成 2-[3-(4-Chlorophenyl)-7-oxa-4-thia-1,2,9,11-tetrazatricyclo[6.4.0.02,6]dodeca-5,8-dien-11-yl]propanoic acid
  参考文献：
  名称：

  New Fungitoxic Fused-Ring Synthetics Incorporating Azoles and Azines in Different Combinations

  摘要：

  2-Aryl-3-thioureido-4-thiazolidinones IIa,b obtained by addition-condensation of aldehyde thiosemicarbazones Ia,b and mercaptoacetic acid underwent chemoselective intramolecular heterocyclizations to 5-aryl-2-mercapto-1,5-dihydrothiazolo[3,4-b]-1,2,4-triazoles IIIa,b, 2-amino-5-aryl-5-hydrothiazolo-[4,3-b]=1,3,4-oxadiazoles IVa,b, and the corresponding thiazolo[4,3-b]-1,3,4-thiadiazoles Va,b with NaOH, I2/NaOH, and concentrated H2SO4, respectively. III-V were condensed with HCHO and alpha-amino acids to yield 7-aryl-2-(carboxyalkyl)thiazolo[3',4':2,3]-1,2,4-triazolo[5,4-b]-1,3,5-thiadiazines VIa-d and 7-aryl-3-(carboxyalkyl)thiazolo[3',4':3,2]-1,3,4-thia(oxa)diazolo[4,5-a]-1,3,5-triazines VIIa-d and VIIIa-d. Fungitoxicities of compounds III-VIII were evaluated in vitro against Aspergillus niger and Fusarium oxysporium. Some of the compounds displayed activities comparable with that of the commercial fungicide Dithane M-45. Structure-activity relationships for the screened compounds are discussed.

  DOI：

  10.1021/jf00039a043

文献信息

• New Fungitoxic Fused-Ring Synthetics Incorporating Azoles and Azines in Different Combinations
  作者：Lal Dhar S. Yadav、Anjum Vaish、Sangeeta Sharma

  DOI：10.1021/jf00039a043

  日期：1994.3

  2-Aryl-3-thioureido-4-thiazolidinones IIa,b obtained by addition-condensation of aldehyde thiosemicarbazones Ia,b and mercaptoacetic acid underwent chemoselective intramolecular heterocyclizations to 5-aryl-2-mercapto-1,5-dihydrothiazolo[3,4-b]-1,2,4-triazoles IIIa,b, 2-amino-5-aryl-5-hydrothiazolo-[4,3-b]=1,3,4-oxadiazoles IVa,b, and the corresponding thiazolo[4,3-b]-1,3,4-thiadiazoles Va,b with NaOH, I2/NaOH, and concentrated H2SO4, respectively. III-V were condensed with HCHO and alpha-amino acids to yield 7-aryl-2-(carboxyalkyl)thiazolo[3',4':2,3]-1,2,4-triazolo[5,4-b]-1,3,5-thiadiazines VIa-d and 7-aryl-3-(carboxyalkyl)thiazolo[3',4':3,2]-1,3,4-thia(oxa)diazolo[4,5-a]-1,3,5-triazines VIIa-d and VIIIa-d. Fungitoxicities of compounds III-VIII were evaluated in vitro against Aspergillus niger and Fusarium oxysporium. Some of the compounds displayed activities comparable with that of the commercial fungicide Dithane M-45. Structure-activity relationships for the screened compounds are discussed.