ethyl 3,5-dimethoxycinnamate

• 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: ethyl 3,5-dimethoxycinnamate
• 英文别名: 3,5-Dimethoxy-zimtsaeureethylester；Ethyl 3,5-dimetoxycinnamate；ethyl 3-(3,5-dimethoxyphenyl)prop-2-enoate
• 化学式: C₁₃H₁₆O₄
• 分子量: 236.268
• InChiKey: BYIUFYLSBXPKEU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 3,5-dimethoxycinnamate 在 palladium on activated charcoal lithium aluminium tetrahydride 、 氢气 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 6.5h， 生成 3-(3,5-二甲氧基苯基)-1-丙醇
  参考文献：
  名称：

  一种简便有效的 3-(3,5-二甲氧基苯基)丙醛合成方法

  摘要：

  摘要描述了一种方便有效的合成 3-(3,5-二甲氧基苯基) 丙醛，这是合成各种生物活性化合物的重要中间体。

  DOI：

  10.1081/scc-120004271
• 作为产物：
  描述：

  白藜芦醇 在 臭氧 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 29.5h， 生成 ethyl 3,5-dimethoxycinnamate
  参考文献：
  名称：

  Stable Isotope Labeling Pattern of Resveratrol and Related Natural Stilbenes

  摘要：

  The stable isotope characterization of resveratrol 1 from Polygonum cuspidatum and of related natural stilbenes 11 and 12 obtained by hydrolysis of the corresponding glucosides 2 and 3 from Rheum is reported. The C-6-C-2-C-6 framework of suitably protected derivatives of 1, 2, and 3 has been degraded with ozone to the C-6-C-1 aldehydes 4, 5, 9, and 10, retaining all hydrogen atoms of the precursors. The natural and synthetic derivatives are characterized and distinguished by natural abundance deuterium nuclear magnetic resonance studies. In the case of anisaldehyde 4 the two series show, as expected, the characteristic difference of the aromatic labeling. The formyl deuterium contents of 4 and 5 from resveratrol are remarkably different, seemingly reflecting the different enrichments existing between positions 3 and 2, respectively, of the phenylpropanoid precursor. The positional delta(18)O values of the extractive materials 1-3 were also determined. In this instance a selective deoxygenation procedure was adopted, leading from 1 to the products 6, 7, and 8. The delta(18)O values of the latter compounds reveal, respectively, those at position 4' and positions 3 and 5 of 1. Similarly, the phenolic products 11 and 12 were converted into 13 and 14. From the delta(18)O values of the single components it is possible to design a detailed map of the oxygen fractionations which characterizes the stilbenes 1-3. In particular, the oxygen present at position 4' of the phenylpropanoid moiety of 1-3 shows delta(18)O values of +11.5, +1.8, and +6.7parts per thousand, respectively. Moreover, the phenolic oxygen atom at position 3' of rhapontin 3 shows a value of +11.7parts per thousand. The data are compared with those previously obtained on structurally related compounds. These results show the utility of simple chemical degradations in the stable isotope characterization of structurally complex food components.

  DOI：

  10.1021/jf011103j

文献信息

• Synthesis of C4C5 Cycloalkyl-Fused and C6-Modified Chromans via<i>ortho</i>-Quinone Methides
  作者：Kassrin Tangdenpaisal、Kanokpish Chuayboonsong、Patchaya Sukjarean、Varisa Katesampao、Nok Noiphrom、Somsak Ruchirawat、Poonsakdi Ploypradith

  DOI：10.1002/asia.201403356

  日期：2015.4

  from 3,5‐dimethoxybenzaldehyde, some functionalized 2,3,4‐trisubstituted tricyclic 4,5‐cycloalkyl‐fused and 6‐modified chromans could be prepared via ortho‐quinone methides (o‐QMs)/hetero‐Diels–Alder (HDA) reactions of the appropriate precursors. The bromide at C6 served as a handle for introducing other substituents through palladium‐catalyzed cross‐coupling reactions and other functional‐group transformations

  从3,5-二甲氧基苯甲醛开始，可以通过邻醌甲基（o -QMs）/杂Diels-Alder（ HDA）适当前体的反应。C6处的溴化物可作为通过钯催化的交叉偶联反应和其他官能团转化引入其他取代基的方法。在[PtCl 4 ]催化下可获得中等至高产率（高达80％）和非对映选择性（高达> 99：1）。优选内切环加成反应中的过渡态中管理在C2的立体化学结果起到了重要作用 C3 C4。在构型上固定Ë双环的几何ö -QMs影响了环加成反应，以有利于C2  C4顺式关系。
• Synthesis of Some Phenylpropanoid Glycosides (PPGs) and Their Acetylcholinesterase/Xanthine Oxidase Inhibitory Activities
  作者：Xiao-Dong Li、Shuai-Tao Kang、Guo-Yu Li、Xian Li、Jin-Hui Wang

  DOI：10.3390/molecules16053580

  日期：——

  In this research, three categories of phenylpropanoid glycosides (PPGs) were designed and synthesized with PPGs isolated from Rhodiola rosea L. as lead compounds. Their inhibitory abilities toward acetylcholinesterase (AChE) and xanthine oxidase (XOD) were also tested. Some of the synthetic PPGs exhibited excellent enzyme inhibitory abilities.

  在这项研究中，设计和合成了三类苯丙素糖苷（PPGs），以从红景天中分离的PPGs作为先导化合物。同时测试了它们对乙酰胆碱酯酶（AChE）和黄嘌呤氧化酶（XOD）的抑制能力。部分合成PPGs表现出了优异的酶抑制能力。
• Asymmetric total synthesis of dihydroisocoumarins: 6-methoxymellein, kigelin and fusarentin 6, 7 dimethyl ether by employing proline catalysed asymmetric α-aminoxylation
  作者：Sachin B. Markad、Baliram B. Mane、Suresh B. Waghmode

  DOI：10.1016/j.tet.2020.131524

  日期：2020.11

  concise asymmetric total synthesis of dihydroisocoumarins such as 6-methoxymellein, kigelin and fusarentin 6,7 dimethyl ether in high enantiopurity have been achieved from non-chiral aldehydes by employing proline catalysed asymmetric α-aminoxylation reaction. The required stereochemistry of hydroxyl group have been generated by alternating L or D proline as a organocatalyst in α-aminoxylation step and

  通过使用脯氨酸催化的不对称α-氨基木糖基化反应，可以从非手性醛类化合物中以高对映体纯度进行简明的不对称全合成二氢异香豆素（如6-甲氧基水杨素，kigelin和fusentin 6,7二甲醚）。所需的羟基立体化学是通过在L-氨氧基化步骤中交替使用L或D脯氨酸作为有机催化剂而生成的，内酯环是通过oxa-Pictet-Spengler环化反应组装的关键步骤。
• Condensation of orthoacetates with aldehydes: a new strategy for the preparation of α,β-unsaturated esters
  作者：H.M. Sampath Kumar、M. Shesha Rao、Sipak Joyasawal、J.S. Yadav

  DOI：10.1016/s0040-4039(03)00815-3

  日期：2003.5

  α,β-Unsaturated esters are formed in good yields when aldehydes are heated with orthoacetates in the presence of a catalytic amount of phenol.

  当醛在催化量的苯酚存在下与原乙酸酯一起加热时，会以高收率形成α，β-不饱和酯。
• Synthesis of 2,3-syn-diarylpent-4-enamides via acyl-Claisen rearrangements of substituted cinnamyl morpholines: application to the synthesis of magnosalicin
  作者：Benjamin D. Dickson、Nora Dittrich、David Barker

  DOI：10.1016/j.tetlet.2012.06.088

  日期：2012.8

  The acyl-Claisen rearrangement of substituted phenylacetyl chlorides and cinnamyl morpholines gives 2,3-syn-diarylpent-4-enamides. Electron-rich cinnamyl morpholines containing alkoxy substituents only reacted with phenylacetyl chlorides; replacement of the phenylacetyl chlorides with alkyl acid chlorides in these reactions gave no rearranged products. Use of the morpholine amides generated in the

  取代的苯基乙酰氯和肉桂基吗啉的酰基-克莱森重排得到2，3-顺式-二芳基戊-4-烯酰胺。含有烷氧基取代基的富电子肉桂基吗啉仅与苯乙酰氯反应；在这些反应中，用烷基酰氯代替苯乙酰氯，没有重排产物。还报道了在天然四氢呋喃新木脂木兰霉素和四苯基四氢呋喃的合成中产生的吗啉酰胺的用途。