(E)-3-(4-methoxyphenyl)-1-morpholinoprop-2-en-1-one | 21497-15-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-3-(4-methoxyphenyl)-1-morpholinoprop-2-en-1-one
• 英文别名: 3-(4-methoxyphenyl)-1-morpholinoprop-2-en-1-one；(E)-4-methoxycinnamic acid morpholinoamide；4-[3-(4-methoxy-phenyl)-acryloyl]-morpholine；trans-p-Methoxy-zimtsaeuremorpholid；(E)-3-(4-methoxyphenyl)-1-morpholin-4-ylprop-2-en-1-one
• CAS: 21497-15-4
• 化学式: C₁₄H₁₇NO₃
• 分子量: 247.294
• InChiKey: JFWXJITUTNBMPU-QPJJXVBHSA-N

物化性质

• 熔点：
  105-107 °C
• 沸点：
  467.7±45.0 °C(Predicted)
• 密度：
  1.162±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-3-(4-methoxyphenyl)-1-morpholinoprop-2-en-1-one 在 叔丁基过氧化氢 叠氮基三甲基硅烷 、 三苯胂氧化物 、 S-1,1'-联-2-萘酚 、 samarium(III) isopropoxide 作用下， 以 四氢呋喃 、 癸烷 为溶剂， 反应 13.0h， 生成 4-[(2R,3R)-3-azido-2-hydroxy-3-(4-methoxyphenyl)-1-oxo-propyl]morpholine
  参考文献：
  名称：

  Dynamic Ligand Exchange of the Lanthanide Complex Leading to Structural and Functional Transformation:  One-Pot Sequential Catalytic Asymmetric Epoxidation-Regioselective Epoxide-Opening Process

  摘要：

  The characteristic property of the lanthanide complex, which easily undergoes a dynamic ligand exchange and alters its structure and function in situ, is described. After the completion of the catalytic asymmetric epoxidation of various a,beta-unsaturated amides 2 in the presence of the Sm-(S)-BINOL-Ph3As=O (1:1:1) complex 1 (2-10 mol %), the addition of Me3SiN3 directly to the reaction mixture led to smooth epoxide-opening at room temperature, affording the corresponding anti-beta-azido-alpha-hydroxyamide 4 in excellent overall yield (up to 99%) with complete regioselectivity and excellent enantiomeric excess (up to >99%). The key to the success of the sequential process was the in situ generation of the highly reactive samarium azide complex through dynamic ligand exchange. In situ IR spectroscopy and other experiments provided strong evidence that the samariurn azide complex was generated. In addition, the relatively high Lewis basicity of the amide moiety had a key role in the high reactivity of both the epoxidation and the epoxide-opening reactions. Examinations of other nucleophiles such as sulfur or carbon nucleophiles as well as transformations of epoxide-opened products are also described.

  DOI：

  10.1021/ja043770+
• 作为产物：
  描述：

  反式-4-甲氧基肉桂酸 在 氯化亚砜 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 生成 (E)-3-(4-methoxyphenyl)-1-morpholinoprop-2-en-1-one
  参考文献：
  名称：

  Synthesis of piplartine analogs and preliminary findings on structure–antimicrobial activity relationship

  摘要：

  In this work it is described the synthesis, characterization and antimicrobial and toxicity evaluation of a series of analogs of piplartine, a piperamide found in Piper sp. The compounds structures were confirmed by infrared spectroscopy, H-1, C-13 nuclear magnetic resonance, high resolution mass spectroscopy and were evaluated against strains of Candida spp., Staphylococcus aureus, Escherichia coli and Pseudomonas aeruginosa. Derivative 24 was almost four-fold more potent (IC50: 48.83 mu M) and five-fold less toxic (SI > 3) than piplartine (IC50: 189.2 mu M; SI: 0.21) against Candida krusei, as well as two-fold more potent than fluconazole (IC50: 104.48 mu M). This compound was also active against Candida tropicalis at 97.67 mu M. Benzoyl derivative 17 was three-fold more potent (IC50: 85.2 mu M) and more than five-fold less toxic (CC50: 231.71 mu M) than piplartine (IC50: 315.33 mu M and CC50: 41.14 mu M) against Staphylococcus aureus. Given these findings, we have found analogs of piplartine which can be assumed as prototypes for the optimization and the development of new antimicrobial (compounds 24 and 17) agents.

  DOI：

  10.1007/s00044-016-1774-9

文献信息

• <i>Z</i>-Selective phosphine promoted 1,4-reduction of ynoates and propynoic amides in the presence of water
  作者：Fabian Seifert、Denis Drikermann、Johannes Steinmetzer、You Zi、Stephan Kupfer、Ivan Vilotijevic

  DOI：10.1039/d1ob00909e

  日期：——

  the selectivity by preventing or reducing the rates of Z- to E-product isomerization. Close reaction monitoring enables isolation of the Z-alkenes with high selectivities. The computational results suggest that the reactions could be highly Z-selective owing to the stereoselective formation of the E-P-hydroxyphosphorane intermediate.

  在水存在下，膦介导的取代丙炔酸酯和酰胺的还原产生了具有高Z选择性的部分还原的 α,β-不饱和酯和酰胺。在某些情况下，产物的竞争性原位 Z对E异构化降低了分离的 α,β-不饱和羰基产物的Z对E比。反应时间和反应混合物中的磷化氢和水的量是通过防止或降低Z - 至E -产物异构化速率来控制选择性的关键实验因素。密切的反应监测可以隔离Z-具有高选择性的烯烃。计算结果表明，由于EP -羟基正膦中间体的立体选择性形成，反应可能是高度Z选择性的。
• Some condensation reactions between aromatic aldehydes and 1,1-bisdialkylaminoalkenes and related compounds
  作者：D. H. R. Barton、G. Hewitt、P. G. Sammes

  DOI：10.1039/j39690000016

  日期：——

  Condensation of 1,1-bisdialkylaminoethenes with aromatic aldehydes gives the corresponding trans-cinnamoyl amides in fair yield. Salicylaldehyde affords coumarin. 1,1-Bisdialkylamino-1,3-dienes and aromatic aldehydes produce 5-arylpenta-cis-2,trans-4-dienoyl dialkylamides. The mechanisms of these reactions have been explored. Some related condensations using 1-alkoxy-1-dialkylaminoethenes and 1-al

  1，1-双二烷基氨基乙烯与芳族醛的缩合以适当的收率得到相应的反式肉桂酰基酰胺。水杨醛提供香豆素。1，1-双二烷基氨基-1，3-二烯和芳族醛产生5-芳基五-顺-2，反式-4-二壬基二烷基酰胺。已经研究了这些反应的机理。还研究了一些使用1-烷氧基-1-二烷基氨基乙烯和1-烷硫基-1-二烷基氨基乙烯的缩合反应。
• CrCl₂-Promoted Stereospecific and Stereoselective Alkyl- and Silylcyclopropanation of α,β-Unsaturated Amides
  作者：José M. Concellón、Humberto Rodríguez-Solla、Carmen Méjica、Elena G. Blanco、Santiago García-Granda、M. Rosario Díaz

  DOI：10.1021/jo800103t

  日期：2008.5.1

  An efficient chromium-promoted alkyl- or silylcyclopropanation of α,β-unsaturated amides is described. These reactions can be carried out on (E)- or (Z)-α,β-enamides in which the C−C double bond is di-, or trisubstituted. This process takes place with total stereospecificity and the new stereogenic center is generated with high or total stereoselectivity. Some synthetic applications of the obtained

  描述了一种有效的铬促进的α，β-不饱和酰胺的烷基或甲硅烷基环丙烷化。这些反应可以在（C）C双键被二或三取代的（E）-或（Z）-α，β-酰胺上进行。该过程以完全立体特异性进行，并且以高或总体立体选择性产生了新的立体异构中心。还报道了所得甲硅烷基环丙基酰胺的一些合成应用。已经提出了基于类胡萝卜素或卡宾配合物的生成的两种机理来解释该环丙烷化反应。
• A Catalytic Asymmetric Synthesis of Chiral Glycidic Acid Derivatives through Chiral Dioxirane-Mediated Catalytic Asymmetric Epoxidation of Cinnamic Acid Derivatives
  作者：Ritsuo Imashiro、Masahiko Seki

  DOI：10.1021/jo049893u

  日期：2004.6.1

  A novel and practical asymmetric synthesis of chiral glycidic acid derivatives involving methyl (2R,3S)-3-(4-methoxyphenyl)glycidate ((2R,3S)-2a), a key intermediate for diltiazem hydrochloride (1), was developed. Treatment of methyl (E)-4-methoxycinnamate ((E)-3a) with chiral dioxirane, generated in situ from a catalytic amount (5 mol %) of an 11-membered C2-symmetric binaphthyl ketone (R)-7a, provided

  一种新颖实用的不对称合成手性缩水甘油酸衍生物，涉及（2 R，3 S）-3-（4-甲氧基苯基）缩水甘油酸甲酯（（2 R，3 S）-2a），这是盐酸地尔硫卓的关键中间体（1） ， 发展了。甲基的处理（ë）-4-甲氧基肉桂酸酯（（ë - ）3a中的11元的）与手性双环氧乙烷，从催化量原位产生（5摩尔％）c ^ 2 -对称联萘酮（[R ）-图7a，提供（2 R，3 S）-2a产率为92％，ee为80％。通过使用相同的方法，将其他肉桂酸酯和酰胺环氧化，得到相应的手性缩水甘油酸衍生物，产率高达95％，ee为92％。观察到（E）-肉桂酸酯不对称环氧化的对映选择性比（E）-二苯乙烯衍生物更高的对映选择性，并被认为归因于肉桂酸酯中的酯基团的氧原子与内酯的氧原子之间的偶极-偶极排斥。联萘基二环氧乙烷中的部分。
• Cobalt-Catalyzed Reductive Carboxylation of α,β-Unsaturated Compounds with Carbon Dioxide
  作者：Chika Hayashi、Takuo Hayashi、Tohru Yamada

  DOI：10.1246/bcsj.20150043

  日期：2015.6.15

  The gaseous carbon dioxide incorporation reaction with α,β-unsaturated compounds was examined in the presence of a catalytic amount of bis(acetylacetonato)cobalt(II) and using diethylzinc as a redu...

  在催化量的双（乙酰​​丙酮）钴 (II) 存在下，并使用二乙基锌作为还原剂，研究了气态二氧化碳与 α,β-不饱和化合物的掺入反应。