2-<(1-pyrrolin-2-yl)thio>acetophenone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-<(1-pyrrolin-2-yl)thio>acetophenone
• 英文别名: 2-[(1-pyrrolin-2-yl)-thio]-acetophenone；2-(3,4-dihydro-2H-pyrrol-5-ylsulfanyl)-1-phenylethanone
• 化学式: C₁₂H₁₃NOS
• 分子量: 219.307
• InChiKey: OQSWVEKFVDIAEJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  54.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-<(1-pyrrolin-2-yl)thio>acetophenone 以66%的产率得到
  参考文献：
  名称：

  FUHRER, W.;RASETTI, V.;RIHS, G., HELV. CHIM. ACTA, 1985, 68, N 5, 1235-1242

  摘要：

  DOI：
• 作为产物：
  描述：

  四氢吡咯-2-硫酮 、 2-溴苯乙酮 以 氯仿 为溶剂， 反应 16.0h， 生成 2-<(1-pyrrolin-2-yl)thio>acetophenone
  参考文献：
  名称：

  两种α，α'-二氨基肟的异常酸催化重排†

  摘要：

  2- [2-（烷亚氨基）-2-苯基亚乙基]吡咯烷（vinamidines，3 - 6）中任一获得经由相应vinologous酰胺活化1与米尔文盐以及中间的后续处理2与胺，或更直接地通过苯乙酮的席夫碱与2-乙氧基-1-吡咯啉的酸催化缩合。这些钒胺的亚硝化产生α，α′-二亚氨基肟。在两种情况下（10，11），这些肟经历酸催化的重排形成5,6,7,8-四氢咪唑并[1,2的一个]吡啶环系（12，13）。提供了这些产物之一（13）和一种Viannaidine盐（6）的X射线分析。

  DOI：

  10.1002/hlca.19850680520

文献信息

• 2-(Iminoethylidene)-pyrrolidines and tautomeric
  申请人：Ciba-Geigy Corporation

  公开号：US04130652A1

  公开（公告）日：1978-12-19

  The present invention provides new imino compounds having the formula I ##STR1## wherein R.sub.1 represents an aliphatic or cycloaliphatic hydrocarbon radical, unsubstituted or substituted phenyl, or phenyl-lower alkyl or diphenyl-lower alkyl, which radicals are unsubstituted or substituted in the phenyl ring(s), R.sub.2 represents unsubstituted or substituted phenyl, unsubstituted or substituted monocyclic heteroaryl or lower alkyl, R.sub.3 represents hydrogen, lower alkyl, a carbonyl group linked with R.sub.2 to form a five-membered ring, or the group R.sub.6 --CO wherein R.sub.6 represents lower alkyl or unsubstituted or substituted phenyl, R.sub.4 represents, if present, hydrogen or lower alkyl which is independent or is linked with R.sub.1 to form a five- to seven-membered ring which can contain as ring members two aromatic ring carbon atoms of an unsubstituted or substituted phenyl or phenyl-lower-alkyl radical R.sub.1, and as a six- or seven-membered ring also epoxy or lower alkylimino which is separated by two, or at least two, carbon atoms from the nitrogen atom given in the formula I, R.sub.5 represents, if present, hydrogen or lower alkyl, A represents a straight- or branched-chain lower alkylene having 2 to (5-n.sub.1 -n.sub.2) chain members, Z represents epoxy, epithio, imino or lower alkylimino, and M.sub.1 and m.sub.2 represent 0 or 1 and together always represent 1, N.sub.1 represents 1 or, if Z represents imino or lower alkylimino and n.sub.2 represents 1, can also represent 0, N.sub.2 represents 0 or 1, And wherein two additional bonds, either corresponding to the dashed lines or corresponding to the dotted lines, are present, with m.sub.1 representing 0 in the former case and m.sub.2 representing 0 in the latter case, and the acid addition salts, in particular the pharmaceutically acceptable acid addition salts thereof. These new substances possess valuable pharmacological properties, particularly hypoglycaemic activity.

  本发明提供了新的亚胺化合物，其具有以下化学式I 其中，R1代表脂肪或环脂烃基，未取代或取代苯基，或苯基-较低烷基或二苯基-较低烷基，这些基团在苯环中未取代或取代；R2代表未取代或取代的苯基，未取代或取代的单环杂环芳基或较低烷基；R3代表氢，较低烷基，与R2连接形成五元环的羰基基团，或R6-CO基团，其中R6代表较低烷基或未取代或取代的苯基；R4代表，如果存在，则为氢或较低烷基，独立或与R1连接形成五至七元环，该环可以包含未取代或取代的苯基或苯基-较低烷基基团R1的两个芳环碳原子作为环成员，并且作为六元或七元环，还可以分离两个或至少两个碳原子与化学式I中给出的氮原子相隔的环氧或较低烷基亚胺基团；R5代表，如果存在，则为氢或较低烷基；A代表具有2到（5-n1-n2）个链成员的直链或支链较低烷基；Z代表环氧、环硫、亚胺或较低烷基亚胺；M1和m2代表0或1，并且总是一起代表1；N1代表1或，如果Z代表亚胺或较低烷基亚胺且n2代表1，则也可以代表0；N2代表0或1；其中存在两个额外的键，可以对应于虚线或点线，m1在前一种情况下表示为0，m2在后一种情况下表示为0，并且酸盐加合物，特别是其药学上可接受的酸盐。这些新物质具有有价值的药理学特性，特别是降血糖活性。
• One-Pot Eschenmoser Episulfide Contractions in DMSO: Applications to the Synthesis of Fuligocandins A and B and a Number of Vinylogous Amides
  作者：Birgitta Pettersson、Vedran Hasimbegovic、Jan Bergman

  DOI：10.1021/jo101864n

  日期：2011.3.18

  Practical total syntheses of the natural products fuligocandin A (2a) and fuligocandin B (3) have been achieved through a convergent strategy depending on the Eschenmoser episulfide contraction as a key step. Conducting the reaction in DAIS proved to be an efficient and general method for the synthesis of a variety of vinylogous amides, such as azepan-2-ylidenepropan-2-one.
• US4130652A
  申请人：——

  公开号：US4130652A

  公开（公告）日：1978-12-19
• US4251542A
  申请人：——

  公开号：US4251542A

  公开（公告）日：1981-02-17