methyl (E)-3-(diethylamino)-2-propenoate | 58243-07-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (E)-3-(diethylamino)-2-propenoate
• 英文别名: methyl (E)-3-(diethylamino)propenoate；methyl (E)-3-diethylaminoacrylate；cis-β-Diaethylamino-acrylsaeure-methylester；methyl (E)-3-(diethylamino)prop-2-enoate
• CAS: 58243-07-5
• 化学式: C₈H₁₅NO₂
• 分子量: 157.213
• InChiKey: RUXDZYKPXMQICT-VOTSOKGWSA-N

物化性质

• 沸点：
  80 °C(Press: 0.01 Torr)
• 密度：
  0.953±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 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：

  methyl (E)-3-(diethylamino)-2-propenoate 在 溴 作用下， 生成 2-Brom-3-diethylamino-acrylsaeuremethylester-hydrobromid
  参考文献：
  名称：

  推挽式烯烃的溴化。II。溴化产物的结构†

  摘要：

  推挽烯烃的溴化反应。II。溴化产物的结构解析

  DOI：

  10.1002/hlca.19770600712
• 作为产物：
  描述：

  N,N-diethylvinylamine 以 四氢呋喃 为溶剂， 生成 methyl (E)-3-(diethylamino)-2-propenoate
  参考文献：
  名称：

  New Reactions of Phosgene with Tertiary Amines

  摘要：

  1-Benzylwye (3) underwent substitution at the 7-position in the presence of COCl2 and pyridine in THF to afford various products depending upon the post-treatment through 1,4-dihydropyridine (7) and carboxylic acid derivative (8). When Et3N was used instead of pyridine, it reacted with COCl2 to provide two enamines (18 and 19), together with diethylcarbamyl chloride (20), after treatment of the reaction mixture with MeOH.

  DOI：

  10.3987/com-97-s37

文献信息

• [EN] METHODS FOR PREPARING NAPHTHYRIDINES<br/>[FR] PROCÉDÉS POUR LA PRÉPARATION DE NAPHTYRIDINES
  申请人：BIONOMICS LTD

  公开号：WO2012151640A1

  公开（公告）日：2012-11-15

  The present invention provides methods of synthesizing compounds of formula (1) and intermediates thereto. The present invention also provides intermediates useful in the synthesis of compounds of formula (1).

  本发明提供了合成式（1）化合物及其中间体的方法。本发明还提供了在合成式（1）化合物中有用的中间体。
• α-Cyclization of tertiary amines. Part 1
  作者：Shuiping Jiang、Zdenek Janousek、Heinz G. Viehe

  DOI：10.1016/0040-4039(94)88019-0

  日期：1994.2

  A general, diastereoselective synthesis of functionalised pyrrolidine, indolizidine, pyrrolizidine and its seven-, eight-membered homologues is reported, starting from readily available enamine esters and acetylenedicarboxylate (DMAD).

  据报道，从容易获得的烯胺酯和乙炔二羧酸酯（DMAD）开始，对官能化的吡咯烷，吲哚并立唑，吡咯烷并其七，八元同系物进行了一般的非对映选择性合成。
• Ring transformation of condensed pyrimidines by enamines and ynamines. Formation of condensed pyridines and condensed diazocines.
  作者：Akira MIYASHITA、Naokata TAIDO、Susumu SATO、Ken-ichi YAMAMOTO、Hitoshi ISHIDA、Takeo HIGASHINO

  DOI：10.1248/cpb.39.282

  日期：——

  A [4+2]-cycloaddition of quinazoline (2) and the 3H-1, 2, 3-triazolo[4, 5-d]pyrimidine 4 with enamines 1a-e resulted in ring transformation into the quinolines, 3a and 3c, and the 3H-1, 2, 3-triazolo[4, 5-b]pyridines, 5a-e, respectively. Similarly, the ynamine 13a cycloadded to 2 and its 4-cyano derivative 6, giving the quinolines, 14a and 14b, respectively.On the other hand, the 3H-1, 2, 3-triazolo[4, 5-d]pyrimidines 4, 15, 8, 16, 17, 18, and 19 underwent [2+2]-cycloaddition with the ynamine 13a, resulting in ring transformation into the corresponding 3H-1, 2, 3-triazolo[4, 5-d]-[1, 3]diazocines 21a-27. The 7-methoxy derivative 20, the 4-methoxy- and 4-cyano-1H-pyrazolo[3, 4-d]pyrimidines, 30 and 31, and the 6-cyano-9H-purine 36 also underwent [2+2]-cycloaddition with 13a to give the corresponding 3H-1, 2-3-triazolo[4, 5-b][1, 5]diazocine 28, 1H-pyrazolo[3, 4-b][1, 5]diazocines, 32 and 33, and 3H-imidazo[4, 5-b]-[1, 5]diazocine 37, respectively.The structures of the 1, 3- and 1, 5-diazocines, 21a and 28, were determined by X-ray crystallography.

  喹唑啉（2）和3H-1, 2, 3-三氮杂[4, 5-d]嘧啶（4）与烯胺（1a-e）进行[4+2]环加成反应，导致环转化为喹啉（3a和3c）和相应的3H-1, 2, 3-三氮杂[4, 5-b]吡啶（5a-e）。类似地，烯氨（13a）与2及其4-氰基衍生物6进行环加成，分别生成喹啉（14a和14b）。另一方面，3H-1, 2, 3-三氮杂[4, 5-d]嘧啶（4、15、8、16、17、18和19）与烯氨（13a）发生[2+2]环加成反应，导致环转化为相应的3H-1, 2, 3-三氮杂[4, 5-d]-[1, 3]二氮环（21a-27）。7-甲氧基衍生物20、4-甲氧基和4-氰基的1H-吡唑[3, 4-d]嘧啶（30和31）以及6-氰基-9H-嘌呤（36）也与13a发生[2+2]环加成，分别生成相应的3H-1, 2-3-三氮杂[4, 5-b][1, 5]二氮环（28）、1H-吡唑[3, 4-b][1, 5]二氮环（32和33）和3H-咪唑[4, 5-b]-[1, 5]二氮环（37）。1, 3-和1, 5-二氮环（21a和28）的结构通过X射线晶体学确定。
• Process for preparing 2-haloalkylnicotinic acids
  申请人：——

  公开号：US20030176468A1

  公开（公告）日：2003-09-18

  The present invention relates to a process for preparing 2-haloalkylnicotinic acids and haloalkylnicotinic acid derivatives starting from halomethyl-substituted enones and 3-dialkylaminoacrylic esters and also to intermediates of the process according to the invention.

  本发明涉及一种从卤甲基取代的烯酮和3-二烷基氨基丙烯酸酯出发制备2-卤代烷基烟酸和卤代烷基烟酸衍生物的方法，以及根据本发明的方法的中间体。
• α-Cyclization of tertiary amines. Part 3. Captodative or push-pull enamines form pyrrolines, pyrrolizidines and their ring homologues with dimethyl acetylenedicarboxylate in a highly diastereoselective reaction
  作者：Benoît De Boeck、Shuiping Jiang、Zdenek Janousek、Heinz G. Viehe

  DOI：10.1016/s0040-4020(01)85235-2

  日期：1994.1

  The title one-pot reaction occurs through a sequence of [2+2] cycloaddition, ring opening to dienamines and formation of a 1,5-dipole by [1,6] hydrogen-shift. This intermediate may cyclize or, in sterically suitable cases and at lower temperatures, lead to isolable N-vinyl enamines by proton transfer.

  通过[2 + 2]环加成，二烯胺开环和通过[1,6]氢转移形成1,5-偶极的过程发生标题一锅反应。该中间体可环化，或在空间上合适的情况下且在较低温度下通过质子转移产生可分离的N-乙烯基烯胺。