1-phenyl-2-(pyrrolidin-2-ylidene)butane-1,3-dione | 64944-81-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-phenyl-2-(pyrrolidin-2-ylidene)butane-1,3-dione
• 英文别名: 1-phenyl-2-pyrrolidin-2-ylidenebutane-1,3-dione
• CAS: 64944-81-6
• 化学式: C₁₄H₁₅NO₂
• 分子量: 229.279
• InChiKey: IBJLUYYFUVYBMK-UHFFFAOYSA-N

物化性质

• 沸点：
  397.9±42.0 °C(Predicted)
• 密度：
  1.148±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  46.17
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-phenyl-2-(pyrrolidin-2-ylidene)butane-1,3-dione 在 甲醇 、 sodium 作用下， 反应 1.0h， 以31%的产率得到1-phenyl-2-(pyrrolidin-2-ylidene)ethanone
  参考文献：
  名称：

  A new bicyclic oxazaborines with a bridged nitrogen atom, their thermic rearrangement and fluorescence properties

  摘要：

  Cyclic beta-enaminones bearing secondary amino group react with 4-substituted benzenediazonium tetraphenylborates in dichloromethane to form substituted bicyclic [1,3,2 lambda(4)] oxazaborines The oxazaborines rearrange, on heating to 200 degrees C in the absence of solvent or in DMF or DMSO, to isomeric 2H-[1,2,4,3 lambda(4)] triazaborines. Previously prepared [1,3,2 lambda(4)] oxazaborines derived from acyclic beta-enaminones bearing secondary amino group either did not undergo the rearrangement or with a lot of difficulties and with negligible yield. The fluorescence behaviour of the prepared triazaborines was observed. These compounds fluoresce in 2-methyltetrahydrofurane and in solid state under low temperatures. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2011.11.004
• 作为产物：
  描述：

  2-甲氧基-1-吡咯烷 、 1-苯基-1,3-丁二酮 在 氮气 、 ethyl acetate n-hexane 作用下， 以 正己烷 为溶剂， 反应 18.0h， 以yields 1-phenyl-2-(2-pyrrolidinylidene)-1,3-butanedione, m.p. 106°-108°的产率得到1-phenyl-2-(pyrrolidin-2-ylidene)butane-1,3-dione
  参考文献：
  名称：

  Imino compounds

  摘要：

  本发明提供了具有以下结构式I的新的亚胺化合物：##STR1## 其中，R.sub.1代表脂肪族或环脂族烃基，未取代或取代的苯基，或苯基-较低烷基或二苯基-较低烷基，所述基团在苯环中未取代或取代，R.sub.2代表未取代或取代的苯基，未取代或取代的单环杂芳基或较低烷基，R.sub.3代表氢、较低烷基、与R.sub.2连接形成五元环的羰基基团，或R.sub.6-CO基团，其中R.sub.6代表较低烷基或未取代或取代的苯基，R.sub.4代表氢或较低烷基（如果存在），其独立或与R.sub.1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R.sub.1的两个芳环碳原子作为环成员，以及六元或七元环中也可以是离氮原子（在式I中给出）两个或至少两个碳原子分离的环氧或较低烷基亚胺基团，R.sub.5代表氢或较低烷基（如果存在），A代表具有2到（5-n.sub.1-n.sub.2）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，m.sub.1和m.sub.2代表0或1，并且总是一起代表1，n.sub.1代表1或，如果Z代表亚胺或较低烷基亚胺且n.sub.2代表1，则也可以代表0，n.sub.2代表0或1，其中存在两个额外的键，或者对应于虚线或对应于点线，m.sub.1在前一种情况下代表0，在后一种情况下m.sub.2代表0，并且酸加成盐，特别是其药学上可接受的酸加成盐。这些新物质具有有价值的药理学特性，特别是降血糖活性，并可用作口服抗糖尿病药物。具体实施例是2-[2-(环己基亚胺)-2-苯乙基]-吡咯烷和2-[2-(顺-2-环己基-环戊基亚胺)-2-苯乙基]-吡咯烷及其药学上可接受的酸加成盐。

  公开号：

  US04251542A1

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.

  本发明提供了具有以下式子I的新亚胺化合物： 其中R1代表脂肪族或环脂族烃基，未取代或取代的苯基，或苯基-低碳基或二苯基-低碳基，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低碳基，R3代表氢、低碳基、与R2连接形成五元环的羰基基团，或R6-CO基团，其中R6代表低碳基或未取代或取代的苯基，R4代表氢或低碳基（如存在），其独立或与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-低碳基基团R1的两个芳环碳原子作为环成员，并且作为六元或七元环，也可以是离氮原子（式I中给出）两个或至少两个碳原子分离的环氧或低碳基亚胺基团，R5代表氢或低碳基（如存在），A代表具有2到（5-n1-n2）链成员的直链或支链低碳基，Z代表环氧、环硫、亚胺或低碳基亚胺，M1和m2代表0或1且总是一起代表1，N1代表1或，如果Z代表亚胺或低碳基亚胺且n2代表1，则还可以代表0，N2代表0或1，其中存在两个额外的键，这些键要么对应于虚线，要么对应于点线，在前一种情况下，m1表示0，在后一种情况下，m2表示0，并且其酸加成盐，特别是其药学上可接受的酸加成盐。这些新物质具有有价值的药理特性，特别是降血糖活性。
• A new bicyclic oxazaborines with a bridged nitrogen atom, their thermic rearrangement and fluorescence properties
  作者：František Josefík、Markéta Svobodová、Valerio Bertolasi、Petr Šimůnek、Vladimír Macháček、Numan Almonasy、Eva Černošková

  DOI：10.1016/j.jorganchem.2011.11.004

  日期：2012.2

  Cyclic beta-enaminones bearing secondary amino group react with 4-substituted benzenediazonium tetraphenylborates in dichloromethane to form substituted bicyclic [1,3,2 lambda(4)] oxazaborines The oxazaborines rearrange, on heating to 200 degrees C in the absence of solvent or in DMF or DMSO, to isomeric 2H-[1,2,4,3 lambda(4)] triazaborines. Previously prepared [1,3,2 lambda(4)] oxazaborines derived from acyclic beta-enaminones bearing secondary amino group either did not undergo the rearrangement or with a lot of difficulties and with negligible yield. The fluorescence behaviour of the prepared triazaborines was observed. These compounds fluoresce in 2-methyltetrahydrofurane and in solid state under low temperatures. (C) 2011 Elsevier B.V. All rights reserved.
• Imino compounds
  申请人：Ciba-Geigy Corporation

  公开号：US04251542A1

  公开（公告）日：1981-02-17

  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, and can be used as oral antidiabetics. Specific embodiments are 2-[2-(cyclohexylimino)-2-phenyl-ethylidene]-pyrrolidine and 2-[2-(cis-2-cyclohexyl-cyclopentylimino)-2-phenylethylidene]-pyrrolidine, and their pharmaceutically acceptable acid addition salts.

  本发明提供了具有以下结构式I的新的亚胺化合物：##STR1## 其中，R.sub.1代表脂肪族或环脂族烃基，未取代或取代的苯基，或苯基-较低烷基或二苯基-较低烷基，所述基团在苯环中未取代或取代，R.sub.2代表未取代或取代的苯基，未取代或取代的单环杂芳基或较低烷基，R.sub.3代表氢、较低烷基、与R.sub.2连接形成五元环的羰基基团，或R.sub.6-CO基团，其中R.sub.6代表较低烷基或未取代或取代的苯基，R.sub.4代表氢或较低烷基（如果存在），其独立或与R.sub.1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R.sub.1的两个芳环碳原子作为环成员，以及六元或七元环中也可以是离氮原子（在式I中给出）两个或至少两个碳原子分离的环氧或较低烷基亚胺基团，R.sub.5代表氢或较低烷基（如果存在），A代表具有2到（5-n.sub.1-n.sub.2）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，m.sub.1和m.sub.2代表0或1，并且总是一起代表1，n.sub.1代表1或，如果Z代表亚胺或较低烷基亚胺且n.sub.2代表1，则也可以代表0，n.sub.2代表0或1，其中存在两个额外的键，或者对应于虚线或对应于点线，m.sub.1在前一种情况下代表0，在后一种情况下m.sub.2代表0，并且酸加成盐，特别是其药学上可接受的酸加成盐。这些新物质具有有价值的药理学特性，特别是降血糖活性，并可用作口服抗糖尿病药物。具体实施例是2-[2-(环己基亚胺)-2-苯乙基]-吡咯烷和2-[2-(顺-2-环己基-环戊基亚胺)-2-苯乙基]-吡咯烷及其药学上可接受的酸加成盐。