2-丙烯醛,3-(2,4,5-三甲氧苯基)- | 106128-88-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醛
• 中文名称: 2-丙烯醛,3-(2,4,5-三甲氧苯基)-
• 英文名称: 2,4,5-trimethoxy cinnamaldehyde
• 英文别名: 2,4,5-trimethoxycinnamaldehyde；asaronaldehyde；trans 2,4,5-trimethoxy cinnamaldehyde；3-(2,4,5-trimethoxyphenyl)prop-2-enal
• CAS: 106128-88-5
• 化学式: C₁₂H₁₄O₄
• 分子量: 222.241
• InChiKey: DNAVOCNYHNNEQI-UHFFFAOYSA-N

物化性质

• 熔点：
  108 °C
• 沸点：
  186 °C(Press: 13 Torr)
• 密度：
  1.112±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  2-丙烯醛,3-(2,4,5-三甲氧苯基)- 在 palladium on activated charcoal manganese(IV) oxide 、 氰化钠 、 氢气 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 28.0h， 生成 methyl 3-(2,4,5-trimethoxyphenyl)propanoate
  参考文献：
  名称：

  Sinha, Arun K.; Dogra, Ruchi; Joshi, Bhupendra P., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2002, vol. 41, # 3, p. 635 - 638

  摘要：

  DOI：
• 作为产物：
  描述：

  顺式-2,4,5-三甲氧基-1-丙烯基苯 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.42h， 生成 2-丙烯醛,3-(2,4,5-三甲氧苯基)-
  参考文献：
  名称：

  Tandem allylic oxidation–condensation/esterification catalyzed by silica gel: an expeditious approach towards antimalarial diaryldienones and enones from natural methoxylated phenylpropenes

  摘要：

  开发了一种新的单锅法策略，利用丰富的甲氧基化苯丙烯类化合物，通过烯丙位氧化-缩合或烯丙位氧化-酯化序列，直接转化为相应的二烯酮（1,5-二芳基-2,4-戊二烯-1-酮）和烯酮（查耳酮和肉桂酸酯）。对上述合成的二芳基二烯酮和烯酮进行的初步抗疟活性研究表明，它们是开发新型经济抗疟药物的有希望的先导候选物。特别是，两个烯酮（12b和13b）的活性（IC50分别为4.0和3.4微摩尔）优于已知的天然抗疟化合物licochalcone（IC50=4.1微摩尔）。

  DOI：

  10.1039/c1ob05293d

文献信息

• Reinvestigation of structure–activity relationship of methoxylated chalcones as antimalarials: Synthesis and evaluation of 2,4,5-trimethoxy substituted patterns as lead candidates derived from abundantly available natural β-asarone
  作者：Rakesh Kumar、Dinesh Mohanakrishnan、Abhishek Sharma、Naveen Kumar Kaushik、Kalpana Kalia、Arun Kumar Sinha、Dinkar Sahal

  DOI：10.1016/j.ejmech.2010.08.049

  日期：2010.11

  causes a decrease. In particular, 2,4,5-trimethoxy substitution pattern at ring A provided potent analogues which were easily derived from abundantly available natural β-asarone rich Acorus calamus oil. Cytotoxic evaluation indicated that the most active compounds 27 (IC50: 1.8 μM) and 26 (IC50: 2 μM) were also relatively non-toxic. Furthermore, compound 12 showed excellent resistance index of 1.1 against

  我们已经使用基于荧光的SYBR Green分析方法检测了一系列甲氧基化查耳酮（A –CH CH–CO– B）对恶性疟原虫（3D7株）的抗疟结构与活性的关系。我们的研究表明，环A上的释放电子的甲氧基和环B上的吸电子基团提高了抗疟药的效力，而这些基团的位置互换导致其降低。特别地，在环2,4,5-三甲氧基取代模式甲提供一种很容易从可大量获得的天然衍生的强效的类似物β细辛醚丰富菖蒲油。细胞毒性评估表明，活性最高的化合物27（IC 50：1.8μM）和26（IC 50：2μM）也是相对无毒的。此外，化合物12对P的耐氯喹Dd2菌株显示出优异的抗性指数1.1 。恶性肿瘤。
• Single step green process for the preparation of substituted cinnamic esters with trans-selectivity
  申请人：Sinha Kumar Arun

  公开号：US20080045742A1

  公开（公告）日：2008-02-21

  The invention provides a green process for direct oxidation of a large number of substituted or unsubstituted cinnamaldehydes or cinnamyl alcohols into the corresponding alkyl or aryl cinnamates in one step. The process of the present invention is a convenient and efficient green process for the preparation of various aryl or alkyl cinnamates under conventional, microwave and ultrasound directly from cinnamaldehydes or cinnamyl alcohols in the presence of an oxidizing agent, catalyst and an alcohol, with or without an organic solvent. These esters are immensely important compounds in flavor, perfumery and pharmaceutical industries. There are several prior arts available for the preparation of cinnamic esters, but all of them suffer from deficiencies such as use of expensive reagents and catalysts, harsh reaction conditions, use of toxic chemicals and others. In contrast, the present methodology is extremely simple and involves reaction of the substrate with an oxidizing agent mixed with a homogeneous or heterogeneous catalyst and an alcohol with or without organic solvent by stirring at room temperature or refluxing or under microwave or ultrasound irradiation to get the requisite products.

  本发明提供了一种绿色工艺，用于将大量取代的或未取代的肉桂醛或肉桂醇直接氧化成相应的烷基或芳基肉桂酸酯的一步法。本发明的过程是一种方便有效的绿色工艺，可以在常规、微波和超声波条件下，在氧化剂、催化剂和醇的存在下，直接从肉桂醛或肉桂醇制得各种芳基或烷基肉桂酸酯，可使用或不使用有机溶剂。这些酯类化合物在香料、香精和医药行业中具有极其重要的作用。尽管存在一些用于制备肉桂酸酯的现有技术，但它们都存在诸如使用昂贵的试剂和催化剂、反应条件苛刻、使用有毒化学品等缺陷。相比之下，本方法极为简单，涉及将底物与氧化剂混合均相或非均相催化剂和醇，在有机溶剂存在下或不存在的条件下，通过在室温下搅拌或回流或微波或超声波照射下反应，以得到所需产品。
• 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。
• [EN] A PROCESS FOR THE PREPARATION OF PHARMACOLOGICALLY ACTIVE ALPHA-ASARONE FROM TOXIC BETA-ASARONE RICH ACORUS CALAMUS OIL<br/>[FR] PROCEDE DE PREPARATION DE ALPHA-ASARONE A ACTIVITE PHARMACOLOGIQUE A PARTIR D'UNE HUILE D'ACORE ODORANT RICHE EN BETA-ASARONE
  申请人：COUNCIL SCIENT IND RES

  公开号：WO2003082786A1

  公开（公告）日：2003-10-09

  The present invention relates to a process for the preparation of high purity and yield α-asarone, trans 2,4,5-trimethoxy cinnamaldehyde, 2,4,5-trimethoxy-phenyl propionone, from β-asarone or β-asarone rich Acorus calamus oil containing α and η-asarone by hydrogenating, followed by treatment with DDQ with or without solid support of silica gel or alumina in dry organic solvent and α-asarone can also be obtained by treating the hydrogenated product of β-asarone or β-asarone rich Acorus calamus with DDQ in an aqueous organic solvent to obtain an intermediate 2,4,5-trimethoxy phenyl propionone, which in turn is reduced with sodiumborohydride to obtain the corresponding 2,4,5-trimethoxy-phenyl propanol and followed by final treatment with a dehydrating agent.

  本发明涉及一种从含有α和η-芳香烃的β-芳香烃或β-芳香烃丰富的菖蒲油中通过加氢后用DDQ处理的高纯度和高产率α-芳香烃、顺式2,4,5-三甲氧基肉桂醛、2,4,5-三甲氧基苯丙酮的制备方法，其中可以在干有机溶剂中使用硅胶或氧化铝固体载体，也可以通过在水有机溶剂中处理β-芳香烃或β-芳香烃丰富的菖蒲油的加氢产物以获得中间体2,4,5-三甲氧基苯丙酮，然后用氢硼酸钠还原获得相应的2,4,5-三甲氧基苯丙醇，最后用脱水剂进行最终处理以获得α-芳香烃。
• Single pot process for the regioselective synthesis of neolignan framework asarones
  申请人：Uppuluri Venkata Mallavadhani

  公开号：US20100099856A1

  公开（公告）日：2010-04-22

  The present invention provides a single pot process for the regioselective synthesis of neolignan framework [3(R)-Ethyl-2(S)-methyl-3-(2″,4″,5″-trimethoxyphenyl)-1-(2′,4′,5′-trimethoxyphenyl)propane from toxic β-isomer rich asarone using montmorillonite acidic clay by employing microwave organic reaction enhancement (MORE) chemistry. This may be useful as versatile synthetic protocol for the synthesis of a large number of lignan and neolignan frameworks.

  本发明提供了一种单锅法过程，用于使用蒙脱石酸性粘土通过采用微波有机反应增强（MORE）化学从有毒的β-异构体富集的asarone中选择性地合成新木兰类骨架[3（R）-乙基-2（S）-甲基-3-（2″，4″，5″-三甲氧基苯基）-1-（2′，4′，5′-三甲氧基苯基）丙烷。这可能是用于合成大量木兰素和新木兰类骨架的通用合成方案。