(2-methylamino-vinyl) phenyl ketone | 56570-44-6

• 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: (2-methylamino-vinyl) phenyl ketone
• 英文别名: 3-methylamino-1-phenylprop-2-en-1-one；(Z)-3-(methylamino)-1-phenylprop-2-en-1-one；PhCOCH=CHNHCH3
• CAS: 56570-44-6
• 化学式: C₁₀H₁₁NO
• 分子量: 161.203
• InChiKey: MGZAGXMLBKSKRX-FPLPWBNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2-methylamino-vinyl) phenyl ketone 在 二氯{（S）-（-）-2,2''-双[二（3,5-二甲苯基）膦基]-1,1''-联萘基}[（2S）-（+）-1,1-双（4-甲氧基苯基）-3-甲基-1,2-丁二胺]钌（II）RuCl2[(S)-xylbinap][(S)-daipen] 、 potassium tert-butylate 、 氢气 作用下， 以 二氯甲烷 、 异丙醇 为溶剂， 20.0 ℃ 、100.0 kPa 条件下， 反应 24.17h， 生成 N-(3-hydroxy-3-phenylpropyl)-N-methylacetamide
  参考文献：
  名称：

  钌催化的β-酮烯胺的不对称加氢：手性γ-氨基醇的一种有效方法

  摘要：

  钌（II）二氯{（S）-（-）-2,2'-双[di（3,5-二甲苯基）膦基] -1,1'-催化的未保护的β-酮烯胺的高效对映选择性氢化双萘基} [（2 S）-（+）-1,1-双（4-甲氧基苯基）-3-甲基-1,2-丁二胺] {Ru [（S）-xylbinap] [（S）-daipen] Cl 2 }已成功开发。这种方法可以直接获取游离的γ-仲氨基醇，这是各种药物和天然产品的关键组成部分，在所有情况下均具有高产率（> 99％）和出色的对映选择性（ee高达99％）。

  DOI：

  10.1002/adsc.201100305
• 作为产物：
  描述：

  苯乙酮 在 potassium hydrogensulfate 作用下， 以 水 为溶剂， 反应 3.0h， 生成 (2-methylamino-vinyl) phenyl ketone
  参考文献：
  名称：

  Devi; Dutta; Nongkhlaw, Journal of the Indian Chemical Society, 2010, vol. 87, # 6, p. 739 - 742

  摘要：

  DOI：

文献信息

• Nuclear magnetic resonance spectral study of β-aminoenones
  作者：Choji Kashima、Hiromu Aoyama、Yasuhiro Yamamoto、Takehiko Nishio、Kazutoshi Yamada

  DOI：10.1039/p29750000665

  日期：——

  The n.m.r. spectra of the four geometrical isomers of β-aminoenones, trans-s-trans, trans-s-cis, cis-s-trans, and cis-s-cis, are discussed. It was found that the chemical shift of the α-proton of β-aminoenones depends on both anisotropic effects and the electron density: δ=δ0–Δδstruc=ΔδAr+K(q–q0). Thus the conformation of non-rigid β-aminoenones can be determined from the observed and the calculated

  β-aminoenones的四个几何异构体的NMR谱，反式-小号-反式，反式-小号-顺式，顺式-小号-反式，以及顺式-小号-顺式，进行了讨论。据发现，β-aminoenones的α质子的化学位移取决于两个各向异性效应和电子密度：δ=δ 0 -Δδ STRUC =Δδ的Ar + ķ（q - q 0）。因此，可以根据观察到的和计算出的α-质子的化学位移来确定非刚性β-氨基烯酮的构象。
• An efficient method for the synthesis of 2-pyridones <i>via</i> C–H bond functionalization
  作者：Shuguang Zhou、Duan-Yang Liu、Suo Wang、Jie-Sheng Tian、Teck-Peng Loh

  DOI：10.1039/d0cc06834a

  日期：——

  A simple and practical method to access N-substituted 2-pyridones via a formal [3+3] annulation of enaminones with acrylates based on RhIII-catalyzed C–H functionalization was developed. Control and deuterated experiments led to a plausible mechanism involving C–H bond cross-coupling and aminolysis cyclization. This strategy provides a short synthesis of structural motifs of N-substituted 2-pyridones

  开发了一种简单实用的方法，通过基于Rh III催化的C–H官能化，通过烯丙酮与丙烯酸酯的正式[3 + 3]环合反应，获得N-取代的2-吡啶酮。对照和氘代实验导致了一个合理的机制，涉及C–H键交叉偶联和氨解环化。该策略提供了N-取代的2-吡啶酮的结构基序的简短合成。
• A facile one-pot synthesis of tetrahydropyrimidines part 3 Synthesis of [alkanediylbis(3-alkyl/aralkyl/aryl-3,6-dihydropyrimidine-1,5(2<i>H</i>)-diyl)bis(arylmethanones) and [1,4-phenylenebis(3-phenyl-3,6-dihydropyrimidine-1,5(2<i>H</i>)-diyl)]bis(phenylmethanone)
  作者：Milan CH. Dutta、Kaushik Chanda、Jai N. Vishwakarma

  DOI：10.1002/jhet.5570420118

  日期：2005.1

  A facile one-pot synthetic strategy has been developed for novel [alkanediylbis(3-alkyl/aralkyl/ aryl-3,6-dihydropyrimidine-1,5(2H)-diyl)]bis(arylmethanones) 2a-c, 2e-m and [1,4-phenylenebis(3-phenyl-3,6-dihydropyrimidine-1,5(2H)-diyl)]bis(phenylmethanone) 2d by refluxing enaminones 1a-f in methanol with diamines and formaldehyde.

  已经开发了一种简便的一锅合成策略，用于新型[烷二基双（3-烷基/芳烷基/芳基-3,6-二氢嘧啶-1,5（2 H）-二基）]双（芳基甲酮）2a-c，2e- m和[1,4-亚苯基双（3-苯基-3,6-二氢嘧啶-1,5（2 H）-二基）]双（苯基甲酮）2d通过在甲醇中将烯胺酮1a-f与二胺和甲醛回流而制得。
• Deuterium Isotope Effects on 13C Chemical Shifts of Enaminones.
  作者：Donka Kh. Zheglova、Daniel G. Genov、Simon Bolvig、Poul Erik Hansen、M. Hanfland、E. Dooryhee

  DOI：10.3891/acta.chem.scand.51-1016

  日期：——

  Deuterium isotope effects on C-13 chemical shifts have been studied in a series of substituted N-alkyl and N-phenyl keto-enamines. The intramolecularly hydrogen bonded Z-forms show the largest two-bond isotope effects, (2) Delta C-1(ND). Methyl-substitution al C-l leads to a larger two-bond isotope effect in the N-phenyl-substituted derivatives. This effect is ascribed to steric compression. Space-filling substituents at the ortho-position of the N-phenyl ring lead to a decrease of the two-bond isotope effect. A correlation is found between (2) Delta C-1(ND) and (3) Delta C-2'(ND). The latter becomes negative in the sterically hindered cases. (3) Delta C-2'(ND) may therefore be used as a gauge of the twist of the phenyl ring.o-Hydroxy substitution of the CO-phenyl rings enables intramolecular hydrogen bonding to the carbonyl group. This kind of hydrogen bond with two donors to one acceptor leads to smaller (2) Delta C-2(ND) and (2) Delta C-2 ''(OD) isotope effects equivalent to weaker hydrogen bonds for the Z-isomer. This is ascribed to competition for the acceptor. For the E-isomer (2) Delta C(OD) is enhanced. The same feature is seen for N,N-dimethylamino enamines. This increase is ascribed to delocalization of the nitrogen lone-pair onto the carbonyl oxygen, thereby strengthening the hydrogen bond and thus leading to larger two-bond, (2) Delta C(OD), isotope effects.
• REACTION OF ENAMINONES WITH THIACUMULENES
  作者：Swapan Kumar Chatterjee、Wolf-Dieter Rudorf

  DOI：10.1080/10426509808032471

  日期：1998.1

  Enaminones 2, easily prepared from the corresponding sodium salts of beta -ketoaldehydes 1 and hydrochlorides of primary amines, react with carbon disulfide/sodium hydride to give dithiocarbamates 3 after alkylation. In a similar way thiocarbamoylation yields isothioureas 4. The C-13 NMR parameters of 2, 3 and 4 show significant low- and high-field shifts of the C-1 and C-2 signals, respectively.