5,6,7,8-Tetrahydroquinoline-8-thiocarboxamide | 53400-60-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 5,6,7,8-Tetrahydroquinoline-8-thiocarboxamide
• 英文别名: 5,6,7,8-tetrahydro-quinoline-8-carbothioic acid amide；5,6,7,8-Tetrahydrochinolin-8-thiocarboxamid；8-Quinolinecarbothioamide, 5,6,7,8-tetrahydro-；5,6,7,8-tetrahydroquinoline-8-carbothioamide
• CAS: 53400-60-5
• 化学式: C₁₀H₁₂N₂S
• 分子量: 192.285
• InChiKey: MUZLJLSOGBHBDC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  71
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5,6,7,8-四氢喹啉 、 5,6,7,8-Tetrahydroquinoline-8-thiocarboxamide 在 正丁基锂 作用下， 以 正己烷 为溶剂， 生成 5,6,7,8-tetrahydro-8-lithioquinoline
  参考文献：
  名称：

  Tetrahydroquinoline derivatives

  摘要：

  本发明涉及新的四氢喹啉衍生物，其是制备抗溃疡剂的中间体。新的衍生物具有以下式子(I)：##STR1## 其中M为钠、钾或锂，R.sup.1、R.sup.2、R.sup.3、R.sup.4、R.sup.5和R.sup.6相同或不同，表示氢、较低的烷基或苯基基团，

  公开号：

  US04160094A1
• 作为产物：
  描述：

  5,6,7,8-四氢喹啉 生成 5,6,7,8-Tetrahydroquinoline-8-thiocarboxamide
  参考文献：
  名称：

  CROSSLEY, R.

  摘要：

  DOI：

文献信息

• Silyl isothiocyanates
  申请人：John Wyeth & Brother Ltd.

  公开号：US04593111A1

  公开（公告）日：1986-06-03

  The invention concerns novel compounds of formula IIIA R.sub.x.sup.a Si(NCS).sub.4-x IIIA wherein R.sup.a is selected from electron donating substituents consisting of alkoxy of 1-10 carbon atoms, cycloalkoxy of 4-8 carbon atoms, aralkoxy of 7-12 carbon atoms, phenoxy which may be substituted by alkyl of 1-10 carbon atoms, alkoxy of 1-10 carbon atoms or trifluoromethyl, the group R.sup.b R.sup.c N-wherein R.sup.b and R.sup.c are selected from alkyl of 1-6 carbon atoms, cycloalkyl of 4-6 carbon atoms, phenyl which may be substituted by alkyl of 1-10 carbon atoms, alkoxy of 1-10 carbon atoms or trifluoromethyl, and aralkyl of 7-12 carbon atoms or R.sup.b and R.sup.c may be joined to form a pyrrolidinyl or piperidinyl ring with the nitrogen atom, which ring may be substituted by alkyl of 1-10 carbon atoms; alkylthio of 1-10 carbon atoms, cycloalkylthio of 4-8 carbon atoms, aralkylthio of 7-12 carbon atoms, phenylthio which may be substituted by alkyl of 1-10 carbon atoms, alkoxy of 1-10 carbon atoms, or trifluoromethyl, and hydrocarbon substituents selected from alkyl of 1-10 carbon atoms, cycloalkyl of 4-8 carbon atoms, aralkyl of 7-12 carbon atoms, or phenyl which may be substituted by alkyl of 1-10 carbon atoms, alkoxy of 1-10 carbon atoms or trifluoromethyl, at least one group R.sup.a being an electron donating substituent with the provisos that: (i) when x is 3 and all three R.sup.a groups are the same alkoxy then the alkoxy group has at least 3 carbon atoms; (ii) when R.sup.a is alkoxy and x is 1 then R.sup.a is other than propoxy; (iii) when one or more R.sup.a are alkylthio and the others (if any) are alkyl then the alkylthio group has at least 2 carbon atoms; (iv) when R.sup.a is aryloxy and x is 3 then at least one group R.sup.a is other than aryloxy. The compounds are useful intermediates in an improved process for preparing fused carbocyclic ring derivatives of pyridine especially 5,6,7,8-tetrahydroquinoline 8-nitriles and thioamides which is described in co-pending U.S. Ser. No. 506,278. The nitriles and thioamides are anti-ulcer and/or anti-secretory agents.

  该发明涉及公式IIIA R.sub.x.sup.a Si(NCS).sub.4-x IIIA的新化合物，其中R.sup.a从以下供电子给体取代物中选择：1-10个碳原子的烷氧基，4-8个碳原子的环烷氧基，7-12个碳原子的芳基氧基，苯氧基，可能被1-10个碳原子的烷基，1-10个碳原子的烷氧基或三氟甲基取代，基团R.sup.b R.sup.c N-其中R.sup.b和R.sup.c从1-6个碳原子的烷基，4-6个碳原子的环烷基，可能被1-10个碳原子的烷基，1-10个碳原子的烷氧基或三氟甲基取代的苯基，7-12个碳原子的芳基或R.sup.b和R.sup.c可以连接形成与氮原子的吡咯啉基或哌啶基，该环可能被1-10个碳原子的烷基取代；1-10个碳原子的烷硫基，4-8个碳原子的环烷硫基，7-12个碳原子的芳基硫基，可能被1-10个碳原子的烷基，1-10个碳原子的烷氧基或三氟甲基取代的苯硫基，以及从1-10个碳原子的烷基，4-8个碳原子的环烷基，7-12个碳原子的芳基，或可能被1-10个碳原子的烷基，1-10个碳原子的烷氧基或三氟甲基取代的苯基的烃取代物中选择的烃基，至少一个基团R.sup.a是一个供电子给体取代物，但需满足以下条件：(i)当x为3且所有三个R.sup.a基团相同时，则烷氧基至少有3个碳原子；(ii)当R.sup.a为烷氧基且x为1时，则R.sup.a不是丙氧基；(iii)当一个或多个R.sup.a为烷硫基而其他的（如果有的话）为烷基时，则烷硫基至少有2个碳原子；(iv)当R.sup.a为芳氧基且x为3时，则至少一个R.sup.a基团不是芳氧基。这些化合物是制备吡啶的融合碳环戒的衍生物的改进过程中的有用中间体，特别是5,6,7,8-四氢喹啉-8-腈和硫酰胺，该过程在共同待决的美国专利申请号506,278中描述。这些腈和硫酰胺是抗溃疡和/或抗分泌剂。
• Preparation of fused carbocyclic ring derivatives of pyridine
  申请人：John Wyeth & Brother Limited

  公开号：US04539406A1

  公开（公告）日：1985-09-03

  An improved process for preparing fused carbocyclic ring derivatives of pyridine especially 5,6,7,8-tetrahydroquinoline 8-nitriles, amides and thioamides is described. The nitriles and thioamides are anti-ulcer and/or anti-secretory agents. Typically a compound of formula A ##STR1## wherein M is sodium, potassium, lithium or MgHal where Hal is chlorine, bromine or iodine, is reacted with a silyl compound R.sub.x.sup.a Si(NCY).sub.4-x III, wherein R.sup.a is selected from electron donating substituents, e.g. alkoxy or dialkylamino, and hydrocarbon substituents e.g. alkyl, at least one R.sup.a being an electron donating substituent, Y is oxygen or sulphur, x has a value from 1 to 3, then subjecting the product to hydrolysis or alcoholysis to obtain the corresponding nitrile, amide or thioamide, provided that when a nitrile is desired the molar ratio of compound III to compound A is at least 2:1 and x is 3 and Y is S. The products may be isolated as acid addition salts. Compound A may carry various substituents e.g. hydrocarbon substituents. Some compounds of formula III are novel and are also claimed.

  描述了一种改进的制备过程，用于合成吡啶的融合碳环衍生物，尤其是5,6,7,8-四氢喹啉8-腈、酰胺和硫代酰胺。这些腈和硫代酰胺是抗溃疡和/或抗分泌剂。通常，式A化合物（其中M是钠、钾、锂或MgHal，Hal是氯、溴或碘）与一个硅基化合物R.sub.x.sup.a Si(NCY).sub.4-x III反应，其中R.sup.a选自电子供体取代基，例如烷氧基或二烷基氨基，以及烃取代基，例如烷基，至少一个R.sup.a是电子供体取代基，Y是氧或硫，x的值从1到3，然后将产物进行水解或醇解以获得相应的腈、酰胺或硫代酰胺，如果需要腈，则化合物III与化合物A的摩尔比至少为2:1，且x为3，Y为S。这些产品可以隔离为酸加成盐。化合物A可以带有各种取代基，例如烃取代基。式III中的一些化合物是新颖的，也申请了专利。
• Process for preparing pyridine derivatives
  申请人：John Wyeth & Brother Limited

  公开号：US04000142A1

  公开（公告）日：1976-12-28

  The invention relates to a process for preparing pyridine compounds which have a fused cycloalkane ring containing an amide, thioamide or nitrile group. The process involves treating a metal derivative of the pyridine compound with a silyl isocyanate or isothiocyanate and then subjecting the product to hydrolysis or alcoholysis.

  这项发明涉及一种制备含有酰胺、硫酰胺或腈基团的融合环烷基环的吡啶化合物的方法。该方法涉及将吡啶化合物的金属衍生物与硅烷异氰酸酯或异硫氰酸酯处理，然后将产物经过水解或醇解。
• Process for preparing cyano derivatives of tetrahydroquinolines and
  申请人：John Wyeth & Brother Limited

  公开号：US04529798A1

  公开（公告）日：1985-07-16

  Fused carbocyclic ring derivatives of pyridine which contain a nitrile or thioamide group on the carbocyclic ring e.g. 8-cyano or thiocarboxamido-5,6,7,8-tetrahydroquinolines are prepared by a process in which a sodium, potassium, lithium or magnesium halide derivative of the pyridine compound is treated with a compound RaRbNCN wherein Ra and Rb are the same or different and represent alkyl, cycloalkyl, or aralkyl, or Ra and Rb are joined to form a heterocyclic ring with the nitrogen, and the product is treated with a proton source to obtain the nitrile which is optionally treated with a sulphurizing agent to form the thioamide. The nitriles or thioamides may be isolated as their acid addition salts.

  含有腈基或硫代酰胺基团的吡啶融合碳环衍生物，例如8-氰基或硫代羧酰胺基-5,6,7,8-四氢喹啉，可通过以下过程制备：用含有钠、钾、锂或镁卤化物衍生物的吡啶化合物处理化合物RaRbNCN，其中Ra和Rb相同或不同，代表烷基、环烷基或芳基，或Ra和Rb连接形成与氮原子相连的杂环环，然后用质子源处理产物以获得腈基，可选择用硫化剂处理腈基以形成硫代酰胺基团。腈基或硫代酰胺基团可作为其酸盐分离。
• Cyclopenteno[b]pyridine derivatives
  申请人：John Wyeth & Brother Limited

  公开号：US04029668A1

  公开（公告）日：1977-06-14

  The invention relates to novel cyclopenteno[b]pyridine derivatives which have a group X on the 7-position and related tricyclic compounds. X is CONHR.sup.3, or CO.sub.2 R.sup.5 wherein R.sup.3 is hydrogen or lower alkyl and R.sup.5 is hydrogen or a lower alkyl or lower aralkyl group which may be substituted by alkyl, alkoxy, halogen, nitro or trifluoromethyl; other substituents may be present. The compounds are intermediates for compounds wherein X is CSNHR.sup.3 which are anti-ulcer agents.

  本发明涉及一种新颖的环戊烯[b]吡啶衍生物，其在7-位上有一个X基团，以及相关的三环化合物。其中X为CONHR.sup.3或CO.sub.2R.sup.5，其中R.sup.3为氢或低碳基，R.sup.5为氢或低碳基或低芳基碳基，其可被烷基、烷氧基、卤素、硝基或三氟甲基取代；其他取代基也可以存在。这些化合物是X为CSNHR.sup.3的化合物的中间体，后者是抗溃疡剂。