alpha-乙基肉桂醛 | 28467-92-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醛
• 中文名称: alpha-乙基肉桂醛
• 英文名称: α-ethylcinnamaldehyde
• 英文别名: 2-ethyl-3-phenyl-2-propenal；benzylidene-2 butanal；2-Ethyl-3-phenyl-2-propenal-(1)；α-Aethyl-zimtaldehyd；2-Aethyl-3-phenyl-acrolein；α-Ethylzimtaldehyd；2-Benzylidenebutanal
• CAS: 28467-92-7
• 化学式: C₁₁H₁₂O
• mdl: MFCD00462497
• 分子量: 160.216
• InChiKey: BOCRJYUZWIOMOJ-UHFFFAOYSA-N

物化性质

• 熔点：
  18°C
• 沸点：
  243°C (estimate)
• 密度：
  1.0201
• LogP：
  3.210 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.181
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2912299000

反应信息

• 作为反应物：
  描述：

  alpha-乙基肉桂醛 生成 3-ethyl-2-phenylquinoline
  参考文献：
  名称：

  Montagne; Roch, Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1941, vol. 213, p. 620,622

  摘要：

  DOI：
• 作为产物：
  描述：

  苯甲醛 、 正丁醛 在 四丁基溴化铵 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 alpha-乙基肉桂醛
  参考文献：
  名称：

  Highly enantioselective bioreduction of 2-fluorocinnamyl alcohols mediated by Saccharomyces cerevisiae

  摘要：

  Biocatalytic reduction of 2-fluorocinnamyl alcohols mediated by Saccharomyces cerevisiae was investigated in phosphate buffer solutions. Product analysis clearly showed that (S)-2-fluoro-3-arylpropanols were afforded in high yields with up to 92% ee Value. (C) 2010 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2010.01.073

文献信息

• Reactions of trimethylsilyl-derived iodohydrins with electron-rich π-systemsElectronic supplementary information (ESI) available: Additional results and experimental data, 1H NMR, 13C NMR and mass spectral data. See http://www.rsc.org/suppdata/p1/b1/b105233k/
  作者：Eti Ishai、Sarit Shamai、Ben-Ami Feit

  DOI：10.1039/b105233k

  日期：2002.1.23

  Reactions of trimethylsilyl-derived iodohydrins of the type R1R2CH–CH(I)OTMS, with electron-rich olefins, and the effects of certain factors on these reactions, were studied. The trimethylsilyl-derived iodohydrins were obtained in situ by reacting R1R2CH–CHO (R1 = R2 = H; R1 = H, R2 = alkyl, phenyl) with TMSI. The corresponding trimethylsilyl enol ether derivatives (R1R2CCH–OTMS), and 1,1-diarylethylenes were the olefins used. Aldehydes of the type RCH2–CHO reacted smoothly in the presence of TMSI to yield the condensation product RCH2–CHC(R)–CHO. Both RCH(–CHCAr2)2 and the cyclic acetal 5 were obtained as main products of the RCHO–TMSI–CH2CAr2 reaction system, depending on the [RCHO] ∶ [TMSI] ∶ [CH2CAr2] concentration ratio. The mechanisms of formation for the various main products and by-products are discussed. TMSI substitutes, formed by reacting Me3SiCl with each of several Lewis acids, were also used.

  研究了从三甲硅基衍生的碘醇R1R2CH-CH(I)OTMS与富电子烯烃的反应，以及某些因素对这些反应的影响。三甲硅基衍生的碘醇是通过R1R2CH-CHO(R1=R2=H;R1=H，R2=烷基、苯基)与TMSI反应在原位获得的。所用的烯烃是相应的三甲硅基烯醇醚衍生物(R1R2CCH-OTMS)和1，1-二芳基乙烯。在TMSI存在下，RCH2-CHO类型的醛顺利反应生成缩合产物RCH2-CHC(R)-CHO。RCHO-TMSI-CH2CAr2反应体系主要生成RCH(-CHCAr2)2和环状缩醛5，这取决于[RCHO]：[TMSI]：[CH2CAr2]的浓度比。讨论了各种主要产物和副产物的形成机理。还使用了通过Me3SiCl与几种Lewis酸反应形成的三甲硅基取代物。
• Highly pH-Dependent Chemoselective Transfer Hydrogenation of α,β-Unsaturated Aldehydes in Water
  作者：Nianhua Luo、Jianhua Liao、Lu Ouyang、Huiling Wen、Jitian Liu、Weiping Tang、Renshi Luo

  DOI：10.1021/acs.organomet.9b00353

  日期：2019.8.12

  electron-poor substituents on the aryl group of α,β-unsaturated aldehydes can be tolerated, affording the corresponding products in excellent yields with high TOF values. High selectivity and yields were also observed for α,β-unsaturated aldehydes with aliphatic substituents. Our mechanistic investigations indicate that the pH value is critical to the chemoselectivity.

  在水中实现了pH依赖的选择性Ir催化的α，β-不饱和醛的加氢反应。在低pH下使用HCOOH作为氢化物供体，仅获得不饱和醇产物，而在高pH下，优先使用HCOONa作为氢化物供体形成饱和醇产物。可以耐受包括α，β-不饱和醛的芳基上的富电子以及贫电子取代基在内的各种官能团，从而以高收率提供具有高收率的相应产物。还观察到具有脂族取代基的α，β-不饱和醛的高选择性和产率。我们的机理研究表明，pH值对化学选择性至关重要。
• Syntheses of hydrido selenophenolato iron(II) complexes and their catalytic application in hydrosilylation of aldehydes and ketones
  作者：Yangyang Wang、Shishuai Ren、Wenbo Zhang、Benjing Xue、Xinghao Qi、Hongjian Sun、Xiaoyan Li、Olaf Fuhr、Dieter Fenske

  DOI：10.1016/j.catcom.2018.06.015

  日期：2018.9

  for this process. Furthermore, α,β-unsaturated alcohols could be obtained from the selective reduction reactions of the corresponding α,β-unsaturated carbonyls catalyzed by hydrido iron(II) complex 5. This catalytic system has good tolerance for some common groups but it is easy to reduce the nitro group to an amino group. The experiments indicate that the chemoselectivity for this catalytic system is

  三种新颖的硒代酚醛氢化铁（II）配合物[顺式-（H）（SeAr）Fe（PMe 3）4 ]（4–6）（Ar = C 6 H 5（4），p -MeOC 6 H 4（5）和ö -MeC 6 ħ 4（6））至铁（PME的反应制备3）4与selenophenols ArSeH（1-3经由硒-H活化）。铁络合物氢基4，5和6可以催化醛和酮的氢化硅烷化。其中络合物5是该方法的最佳催化剂。此外，由氢化铁（II）配合物5催化的相应α，β-不饱和羰基的选择性还原反应可以得到α，β-不饱和醇。该催化体系对某些常见基团具有良好的耐受性，但易于将硝基还原为氨基。实验表明，该催化体系的化学选择性为CHO> NO 2 > C（O）CH 3。通过X射线衍射确定6的晶体结构。
• A simple and efficient synthesis of pyrazoles in water
  作者：Jun Wen、Yun Fu、Ruo-Yi Zhang、Ji Zhang、Shan-Yong Chen、Xiao-Qi Yu

  DOI：10.1016/j.tet.2011.09.074

  日期：2011.12

  A simple, highly efficient, and environmentally friendly method for the synthesis of substituted 1H-pyrazoles by one-pot condensation reaction of α,β-unsaturated carbonyl compounds with tosyl hydrazide in water was developed. The reaction system exhibited tolerance with various functional groups, Aromatic moiety with both electron-rich and electron-deficient substituents could give desired products

  开发了一种简单，高效，环境友好的方法，该方法通过α，β-不饱和羰基化合物与甲苯磺酰肼在水中的一锅缩合反应合成取代的1 H-吡唑。该反应体系表现出对各种官能团的耐受性，同时具有富电子和缺电子取代基的芳族部分可以良好至极佳的收率得到所需的产物。
• Pd-catalyzed oxidative amidation of aldehydes with hydrogen peroxide
  作者：Yutaka Suto、Noriyuki Yamagiwa、Yasuhiro Torisawa

  DOI：10.1016/j.tetlet.2008.07.075

  日期：2008.9

  Using hydrogen peroxide as a key oxidant, catalytic oxidative amidation between aldehydes and amines was effectively carried out with PdCl2–xantophos as a catalyst in methanol under acidic conditions. The new protocol is mechanistically different from the previous one through β-hydride elimination.

  使用过氧化氢作为主要氧化剂，在酸性条件下，以PdCl 2 -xantophos作为催化剂在甲醇中有效地进行了醛和胺之间的催化氧化酰胺化反应。通过消除β-氢化物，新方案与以前的方案在机械上有所不同。