dihydro-3-[(dimethylamino)methylene]-2(3H)-furanone | 34009-40-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: dihydro-3-[(dimethylamino)methylene]-2(3H)-furanone
• 英文别名: 3-[(dimethylamino)methylene]dihydro-2(3H)-furanone；2(3H)-Furanone, 3-[(dimethylamino)methylene]dihydro-, (3E)-；(3E)-3-(dimethylaminomethylidene)oxolan-2-one
• CAS: 34009-40-0
• 化学式: C₇H₁₁NO₂
• 分子量: 141.17
• InChiKey: TVGHSXBYKSMSHY-AATRIKPKSA-N

物化性质

• 熔点：
  97-99 °C(Solv: ethyl ether (60-29-7))
• 沸点：
  143-155 °C(Press: 2.66 Torr)
• 密度：
  1.204±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  dihydro-3-[(dimethylamino)methylene]-2(3H)-furanone 在 正丁基锂 、 氘代甲醇-d 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 生成 (3E)-3-[deuterio(dimethylamino)methylidene]oxolan-2-one
  参考文献：
  名称：

  取代基对丙烯酸衍生物形成乙烯基锂区域选择性的影响

  摘要：

  β-烷氧基，β-二烷基氨基和β-N-烷基酰基氨基取代基决定丙烯酸酯和腈衍生物的乙烯基去质子化的区域选择性：可能会生成α-或β-乙烯基锂物种。具有额外的α-烷基或α-甲基巯基取代基的相应的丙烯酰胺或体系在β-位被锂化。

  DOI：

  10.1016/s0040-4039(01)82926-9
• 作为产物：
  描述：

  2,3-二氢-4-三氯乙酰基呋喃 、 二甲胺 以 甲醇 、 水 为溶剂， 反应 1.0h， 以85%的产率得到dihydro-3-[(dimethylamino)methylene]-2(3H)-furanone
  参考文献：
  名称：

  Convenient synthesis of 3-aminomethylenedihydrofuran-2-ones

  摘要：

  A simple and convenient synthesis of a series of 3-aminomethylenedihydrofuran-2-ones from the reaction of 3-trichloroacetyl-4,5-dihydrofuran with amines, is presented. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02744-2

文献信息

• [EN] ENAMINOCARBONYL COMPOUNDS AND THEIR USE<br/>[FR] COMPOSÉS D'ÉNAMINOCARBONYLE ET LEUR UTILISATION
  申请人：INST CHEMII ORGANICZNEJ POLSKA

  公开号：WO2010087727A1

  公开（公告）日：2010-08-05

  The present invention relates to enaminocarbonyl compounds with the formula I, in which X denotes O or CH2, Y denotes N and each of R1 and R2 denotes hydrogen, or Y denotes a CH and either R1 or R2 denotes a C1-4 alkyl, and the remaining R1 or R2 denotes hydrogen, selected (for Y denoting CH and R1 or R2 denoting a C1-4 alkyl) from a group encompassing a mixture of R and S enantiomers enriched in either enantiomer R or enantiomer S, enantiomer R and enantiomer S. The present invention also relates to the use of compounds with the formula I, in which X denotes O or CH2, Y denotes a CH and either R1 or R2 is selected from a group encompassing hydrogen and a C1-4 alkyl, and the remaining R1 or R2 denotes hydrogen, for the modification of the taste of a product and/or preparation for oral administration.

  本发明涉及具有式I的恩酰胺羰基化合物，其中X表示O或CH2，Y表示N，并且R1和R2中的每一个表示氢，或者Y表示CH且R1或R2表示C1-4烷基，剩余的R1或R2表示氢，从一个包含富集于R或S对映体的R和S对映体混合物的群体中选择（对于Y表示CH且R1或R2表示C1-4烷基），对映体R和对映体S。本发明还涉及具有式I的化合物的用途，其中X表示O或CH2，Y表示CH，且R1或R2从包括氢和C1-4烷基的群体中选择，剩余的R1或R2表示氢，用于改善产品的口味和/或口服制剂的调整。
• [4 + 2]-Cycloaddition Reactions between β-Acceptor-Substituted Enamines and 2-Vinylindole Radical Cations Acting as Hetero-Dienes
  作者：Christoph F. Gürtler、Eberhard Steckhan、Siegfried Blechert

  DOI：10.1021/jo951551o

  日期：1996.1.1

  [4 + 2]-Cycloaddition reactions between 2-vinylindoles acting as hetero-dienes and beta-acceptor substituted cyclic and acyclic enamines can be induced by formation of 2-vinylindole radical cations either via anodic oxidation or photoelectron transfer (PET) using catalytic amounts of triarylpyrylium tetrafluoroborates as sensitizers. In this way, pyrido[1,2-a]indoles or indolo[1,2-a]hexahydro-1,8-naphthyridines

  充当杂二烯的2-乙烯基吲哚与β-受体取代的环状和无环烯胺之间的[4 + 2]-环加成反应可以通过使用催化量的阳极氧化或光电子转移（PET）形成2-乙烯基吲哚自由基阳离子来诱导四氟硼酸三芳基吡啶鎓作为敏化剂。以此方式，在完整的区域和立体化学控制下，一步形成吡啶并[1,2-a]吲哚或吲哚[1,2-a]六氢-1,8-萘啶。
• 4H-pyrimido[2,1-a]isoquinolin-4-one derivatives
  申请人：G. D. Searle & Co.

  公开号：US04661592A1

  公开（公告）日：1987-04-28

  This invention relates to a class of novel 4H-pyrimido[2,1-a]isoquinoline derivatives. The invention further relates to pharmaceutical compositions containing such 4H-pyrimido[2,1-a]isoquinoline-4-one derivatives and to the use of such compounds and compositions as anorectic agents. In particular, the novel 4H-pyrimido[2,1-a]isoquinoline-4-one derivatives are effective anorectic agents when administered orally.

  本发明涉及一类新型的4H-嘧啶并[2,1-a]异喹啉衍生物。本发明还涉及含有这种4H-嘧啶并[2,1-a]异喹啉-4-酮衍生物的制药组合物以及将这些化合物和组合物用作抑食剂。特别地，当口服时，这些新型的4H-嘧啶并[2,1-a]异喹啉-4-酮衍生物是有效的抑食剂。
• ENAMINOCARBONYL COMPOUNDS AND THEIR USE
  申请人：Krajewski Piotr

  公开号：US20110274803A1

  公开（公告）日：2011-11-10

  The present invention relates to enaminocarbonyl compounds with the formula I, in which X denotes O or CH 2 , Y denotes N and each of R 1 and R 2 denotes hydrogen, or Y denotes a CH and either R 1 or R 2 denotes a C1-4 alkyl, and the remaining R 1 or R 2 denotes hydrogen, selected (for Y denoting CH and R 1 or R 2 denoting a C 1-4 alkyl) from a group encompassing a mixture of R and S enantiomers enriched in either enantiomer R or enantiomer S, enantiomer R and enantiomer S. The present invention also relates to the use of compounds with the formula I, in which X denotes O or CH 2 , Y denotes a CH and either R 1 or R 2 is selected from a group encompassing hydrogen and a C 1-4 alkyl, and the remaining R 1 or R 2 denotes hydrogen, for the modification of the taste of a product and/or preparation for oral administration.

  本发明涉及具有公式I的烯胺酰基化合物，其中X表示O或CH2，Y表示N，且R1和R2中的每一个表示氢，或Y表示CH且R1或R2中的一个表示C1-4烷基，其余的R1或R2表示氢，所选的（对于Y表示CH且R1或R2表示C1-4烷基）从包括富集于R或S对映体的混合物、对映体R或对映体S中选择。本发明还涉及具有公式I的化合物的用途，其中X表示O或CH2，Y表示CH且R1或R2中的一个从包括氢和C1-4烷基的群中选择，其余的R1或R2表示氢，用于改变产品和/或口服制剂的口感。
• Electrochemically Induced Hetero-[4+2]-Cycloaddition Reactions Between 2-Vinylpyrroles andβ-Acceptor-Substituted Enamines
  作者：Thomas Peglow、Siegfried Blechert、Eberhard Steckhan

  DOI：10.1002/(sici)1521-3765(199801)4:1<107::aid-chem107>3.0.co;2-e

  日期：1998.1

  Recently, we reported on radical cation cycloaddition reactions between 2-vinylindoles and beta-acceptor-substituted enamines, which provide a new pathway to pyrido[1,2-a] indoles.([1]) In order to broaden the synthetic scope of this reaction, we have developed hetero-[4+2]-cycloaddition reactions between a number of readily accessible 2-vinylpyrroles, acting as heterodienes, and beta-acceptor-substituted enamines. This reaction is induced by electrochemically generated radical cations of either the 2-vinylpyrrole diene or the enamine dienophile. These electron-transfer-induced reactions open up a novel route to highly substituted indolizines in moderate yields. We propose a mechanism that explains both the complete regio-control of this cycloaddition as well as the product formation, irrespective of the inducing radical cation species.