ethyl 1-amino-8,8-dimethyl-5-(piperidin-1-yl)-8,9-dihydro-6H-pyrano[4,3-d]thieno[2,3-b]pyridine-2-carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃吡啶类
• 英文名称: ethyl 1-amino-8,8-dimethyl-5-(piperidin-1-yl)-8,9-dihydro-6H-pyrano[4,3-d]thieno[2,3-b]pyridine-2-carboxylate
• 英文别名: ethyl1-amino-8,8-dimethyl-5-(piperidin-1-yl)-8,9-dihydro-6H-pyrano[4,3-d]thieno[2,3-b]pyridine-2-carboxylate；ethyl 3-amino-12,12-dimethyl-8-piperidin-1-yl-11-oxa-5-thia-7-azatricyclo[7.4.0.02,6]trideca-1(9),2(6),3,7-tetraene-4-carboxylate
• 化学式: C₂₀H₂₇N₃O₃S
• mdl: MFCD01956992
• 分子量: 389.519
• InChiKey: DMWFSRNRABKAON-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  106
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl 1-amino-8,8-dimethyl-5-(piperidin-1-yl)-8,9-dihydro-6H-pyrano[4,3-d]thieno[2,3-b]pyridine-2-carboxylate 在 甲酸 、 hydrazine hydrate 、 N,N-二甲基甲酰胺 、 三氯氧磷 作用下， 以 正丁醇 为溶剂， 反应 27.0h， 生成 8,8-dimethyl-11-(piperidin-1-yl)-7,10-dihydro-8H-pyrano[4'',3'':4',5']pyrido[3',2':4,5]thieno[2,3-e][1,2,4]triazolo[1,5-c]pyrimidine
  参考文献：
  名称：

  synthesis of (piperidin-1-yl)trihydropyrano(cyclopenta)-[4′,5′]pyrido[3′,2′: 4,5]thieno[3,2-e][1,2,4]triazolo-[4,3-c(1,5-c)]pyrimidines

  摘要：

  Reactions of 3-cyanopyridine-2(1H)-thiones with ethyl chloroacetate and chloroacetamide gave the corresponding amino-substituted thieno[2,3-b]pyridines which were treated with formamide or ethyl formate to obtain fused pyridothieno[3,2-d]pyrimidinones. The latter were converted into hydrazino derivatives whose cyclocondensation with triethyl orthoformate or formic acid afforded 7,10-dihydro-8H-pyranopyridothienopyrimidines and 2,3-dihydro-1H-cyclopentapyridothienopyrimidines annulated by triazole ring at the pyrimidine ring.

  DOI：

  10.1134/s1070428014120203
• 作为产物：
  描述：

  ethyl {[5-cyano-3,3-dimethyl-8-(piperidin-1-yl)-3,4-dihydro-1H-pyrano[3,4-c]pyridin-6-yl]sulfanyl}-acetate 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以97%的产率得到ethyl 1-amino-8,8-dimethyl-5-(piperidin-1-yl)-8,9-dihydro-6H-pyrano[4,3-d]thieno[2,3-b]pyridine-2-carboxylate
  参考文献：
  名称：

  synthesis of (piperidin-1-yl)trihydropyrano(cyclopenta)-[4′,5′]pyrido[3′,2′: 4,5]thieno[3,2-e][1,2,4]triazolo-[4,3-c(1,5-c)]pyrimidines

  摘要：

  Reactions of 3-cyanopyridine-2(1H)-thiones with ethyl chloroacetate and chloroacetamide gave the corresponding amino-substituted thieno[2,3-b]pyridines which were treated with formamide or ethyl formate to obtain fused pyridothieno[3,2-d]pyrimidinones. The latter were converted into hydrazino derivatives whose cyclocondensation with triethyl orthoformate or formic acid afforded 7,10-dihydro-8H-pyranopyridothienopyrimidines and 2,3-dihydro-1H-cyclopentapyridothienopyrimidines annulated by triazole ring at the pyrimidine ring.

  DOI：

  10.1134/s1070428014120203

文献信息

• Synthesis of 5,8-Diamino-Substituted Pyrano[4″,3″:4′,5′]pyrido[3′,2′:4,5]thieno[3,2-d]pyrimidines and Pyrimido[4′,5′:4,5]thieno[2,3-c]isoquinolines
  作者：E. G. Paronikyan、Sh. Sh. Dashyan、N. S. Minasyan、G. M. Stepanyan

  DOI：10.1134/s1070428016040187

  日期：2016.4

  corresponding 1-thioureido derivatives which underwent cyclization to 2,2-dimethyl-5-(piperidin-1-yl)-10-thioxo-1,4,10,11-tetrahydro-2H-pyrano[4″,3″:4′,5′]pyrido-[3′,2′:4,5]thieno[3,2-d]pyrimidin-8(9H)-one and 5-(piperidin-1-yl)-10-thioxo-1,2,3,4,10,11-hexahydropyrimido-[4′,5′:4,5]thieno[2,3-c]isoquinolin-8(9H)-one. The cyclization products were converted into 8-chloro derivatives, and the chlorine atom therein

  乙基1-氨基-8,8-二甲基-5-（哌啶-1-基）-8,9-二氢-6- ħ吡喃并[4,3- d ]噻吩并[2,3- b ]吡啶-2-羧酸盐和1-氨基-5-（哌啶-1-基）-6,7,8,9-四氢噻吩并[2,3 - c ]异喹啉-2-羧酸乙酯与苯甲酰基异硫氰酸酯反应生成相应的1-硫脲基衍生物进行环化成2,2-二甲基-5-（哌啶-1-基）-10-硫代-1,4,10,11-四氢-2 H-吡喃[4“，3”：4'，5' ] pyrido- [3'，2'：4,5] thieno [3,2- d ] pyrimidin-8（9 H）-one和5-（piperidin-1-yl）-10-thioxo-1,2， 3,4,10,11-六氢嘧啶基-[4'，5'：4,5]噻吩并[2,3 - c ]异喹啉-8（9 H）-一。将环化产物转化为8-氯衍生物，并用各种胺代替其中的氯原子。