2-diethylamino-3-phenylpropenal | 176374-17-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醛
• 英文名称: 2-diethylamino-3-phenylpropenal
• 英文别名: α-N,N-diethylaminocinnamaldehyde；2-Diethylamino-3-phenylpropenal；2-(diethylamino)-3-phenylprop-2-enal
• CAS: 176374-17-7
• 化学式: C₁₃H₁₇NO
• 分子量: 203.284
• InChiKey: WEQRIQOXUNHBLH-UHFFFAOYSA-N

物化性质

• 沸点：
  340.8±35.0 °C(Predicted)
• 密度：
  1.012±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  二甲基三甲硅基膦酸酯 、 2-diethylamino-3-phenylpropenal 反应 2.0h， 以78%的产率得到dimethyl 2-diethylamino-3-phenyl-1-trimethylsiloxy-1-propenephosphonate
  参考文献：
  名称：

  Captodative Formyl Enamines in a New Synthesis of Tertiary α-Amino Esters

  摘要：

  一种将–CH(NR2)CO-基团从捕获稳定的形式亚胺成功应用于合成三级α-氨基酯的策略。

  DOI：

  10.3390/61100892
• 作为产物：
  描述：

  (2Z)-2-bromo-3-phenyl-2-propenal 、 二乙胺 以 乙醚 为溶剂， 生成 2-(diethylamino)-3-phenylacrylaldehyde 、 2-diethylamino-3-phenylpropenal
  参考文献：
  名称：

  Klein, Jean-Louis; Combret, Jean-Claude, Bulletin de la Societe Chimique de France, 1983, vol. 2, # 1-2, p. 28 - 32

  摘要：

  DOI：

文献信息

• Reactions of ?-halo-?, ?-unsaturated aldehydes with secondary amines
  作者：A. Yu. Raley、N. A. Keiko、M. G. Poronkov

  DOI：10.1007/bf01433745

  日期：1996.1

  Reactions of 2-halo-2-alkenals R″(R′)C=CX-CHO with secondary amines R2NH occur asipso-substitution of the halogen atom, along with fragmentation and condensation, yielding 1,2-diaminoethenes R2NCH=CHNR2, carbonyl compounds R″C(O)R′, 1,3-bis(amino)-2-haloolefins R″(R′)C(NR2)CX=CHNR2, and formamides R2NCHO. The ratio between the competing reactions depends on the structure of the starting compounds and

  2-halo-2-alkenals R″(R')C=CX-CHO 与仲胺 R2NH 的反应发生卤原子的同位取代，以及裂解和缩合，产生 1,2-二氨基乙烯 R2NCH=CHNR2，羰基化合物 R"C(O)R'、1,3-双(氨基)-2-卤代烯烃 R"(R')C(NR2)CX=CHNR2 和甲酰胺 R2NCHO。竞争反应之间的比率取决于起始化合物的结构和实验条件。
• Transformations des énamines α-formylées: synthèse d’α-amino esters N,N-disubstitués
  作者：Alexander Yu. Rulev、Lyudmila I. Larina、Mikhail G. Voronkov

  DOI：10.1016/s0040-4039(00)01838-4

  日期：2000.12

  2-Dialkylaminoalkanoic esters are prepared in moderate yield by the reaction of N,N-disubstituted 2-amino-2-alkenals with dialkyl phosphonates in the presence of sodium alcoxide. A mechanism involving an α-keto-β-aminophosphonate as an intermediate is proposed.

  通过使N，N-二取代的2-氨基-2-烯醛与二烷基膦酸酯在氧化钠的存在下反应，以中等收率制备2-二烷基氨基链烷酸酯。提出了以α-酮-β-氨基膦酸酯为中间体的机理。
• Reactions of α-Functionally Substituted Enals with Terminal Alkynes: Unexpected Assembly of 2-Amino-2-Cyclopentenones
  作者：Rustam B. Shnigirev、Igor A. Ushakov、Valentin A. Semenov、Alexander Yu. Rulev

  DOI：10.1021/acs.joc.3c00340

  日期：——

  α-amino functionally substituted enals with terminal alkynes leading either to corresponding propargyl alcohols (for O-, S-, Cl-, and Br-bearing substrates) or unexpected 2-amino-2-cyclopentenones (for aminoenals) are described. The key feature of these reactions is the rearrangement of adducts bearing amino groups on silica gel that triggered further cyclization to five-membered carbocycles.

  α-硫属元素、α-卤素或 α-氨基功能取代的烯醛与末端炔烃的反应导致相应的炔丙醇（对于含 O-、S-、Cl- 和 Br 的底物）或意想不到的 2-氨基-描述了 2-环戊烯酮（对于氨基烯醛）。这些反应的关键特征是硅胶上带有氨基的加合物的重排，引发进一步环化为五元碳环。
• ——
  作者：A. Yu. Rulev、L. I. Larina、M. G. Voronkov

  DOI：10.1023/a:1014232124751

  日期：——

  alpha-Acylenamines with terminal double bond CH2=CH(NR2)COMe add dialkyl hydrogen phosphites to form only the Michaelis adducts. Contrary to that hydrophosphorylation of a-formylated enamines proceeds regiospecifically at C=O bond. Subsequent isomerization of the products of 1,2-addition and the cleavage of P-C bond of the intermediate alpha-keto-beta-aminophosphonate yields N, N-disubstituted alpha-aminocarboxylates.
• UV Spectra and Structure of 2-Diethylamino-3-phenylpropenal: Enamine or Enal?
  作者：N. N. Chipanina、A. Yu. Rulev、L. V. Sherstyannikova、L. V. Kanitskaya、S. V. Fedorov、V. K. Turchaninov

  DOI：10.1023/b:rujo.0000013128.70004.32

  日期：2003.11

  According to the data of UV, IR, H-1 and (NMR)-N-13 spectra and also quantum-chemical calculations (B3LYP/631G*), Z- and E-isomers of 2-diethylamino-3-phenylpropenal in inert environment exist as antiperiplanar conformers. The energy of electron transitions therein depends on the orientation both f the benzene ring and the unshared electron pair of the nitrogen with respect to the C=C bond. 2-Diethylamino3-phenylpropenal is an enamine, but the extent of the ppi(*) interaction in its prevailing Z-isomer is small.