2-丙烯醛,3-(2,4,5-三甲氧苯基)- | 99217-07-9

• 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: trans 2,4,5-trimethoxy cinnamaldehyde
• 英文别名: (E)-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-al；(E)-3-(2,4,5-trimethoxyphenyl)acrylaldehyde；trans-3-(2,4,5-trimethoxyphenyl)prop-2-enal；(E)-3-(2,4,5-trimethoxyphenyl)-propen-2-al；(E)-3-(2,4,5-trimethoxyphenyl)propenal；(E)-2,4,5-trimethoxycinnamaldehyde；2,4,5-Trimethoxy cinnamaldehyde；(E)-3-(2,4,5-trimethoxyphenyl)prop-2-enal
• CAS: 99217-07-9；106128-88-5；99217-06-8
• 化学式: C₁₂H₁₄O₄
• 分子量: 222.241
• InChiKey: DNAVOCNYHNNEQI-SNAWJCMRSA-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)
• 保留指数：
  1845

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 sodium tetrahydroborate 作用下， 以 甲醇 、 溶剂黄146 为溶剂， 反应 12.0h， 生成 1,2,4-三甲氧基-5-丙-2-烯基苯
  参考文献：
  名称：

  一个温和方便的方法，可以将有毒的β-细辛胺转化为稀有的苯丙烷类化合物：2,4,5-三甲氧基肉桂醛和γ-细辛。

  摘要：

  用DDQ氧化β-花生四烯醛（2）得到反式2,4,5-三甲氧基肉桂醛（3），用对甲苯磺酰基肼处理后得到相应的α，β-不饱和衍生物（4）。用硼氢化钠在乙酸中还原4，以43％的收率得到γ-asaron（1）。

  DOI：

  10.1021/np010559s
• 作为产物：
  描述：

  1,2,4-三甲氧基-5-丙-2-烯基苯 在 sodium dichromate 、 alkaline medium 作用下， 以 溶剂黄146 、 苯 为溶剂， 反应 7.0h， 生成 2-丙烯醛,3-(2,4,5-三甲氧苯基)-
  参考文献：
  名称：

  Kulkarni, Mandakini M.; Sohoni, Jayant S.; Rojatkar, Supada R., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1986, vol. 25, p. 981 - 982

  摘要：

  DOI：

文献信息

• 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。
• Process for the preparation of pharmacologically active &agr;-asarone from toxic &bgr;-asarone rich acorus calamus oil
  申请人：Council of Scientific & Industrial Research

  公开号：US06590127B1

  公开（公告）日：2003-07-08

  The present invention relates to a process for the preparation of high purity and yield &agr;-asarone, trans 2,4,5-trimethoxy cinnamaldehyde, 2,4,5-trimethoxy-phenyl propionone, from &bgr;-asarone or &bgr;-asarone rich Acorus calamus oil containing &agr; and &ggr;-asarone by hydrogenating, followed by treatment with DDQ with or without solid support of silica gel or alumina in dry organic solvent and &agr;-asarone can also be obtained by treating the hydrogenated product of &bgr;-asarone or &bgr;-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γ-芳香烯的β-芳香烯或富含β-芳香烯的菖蒲油中，通过加氢后用DDQ处理（可带有硅胶或氧化铝的固体支持）的干有机溶剂，制备高纯度和高产率的α-芳香烯、反式2,4,5-三甲氧基肉桂醛、2,4,5-三甲氧基苯基丙酮。也可以通过将β-芳香烯或富含β-芳香烯的菖蒲油的加氢产物用DDQ在水有机溶剂中处理，得到中间体2,4,5-三甲氧基苯基丙酮，然后用硼氢化钠还原得到相应的2,4,5-三甲氧基苯基丙醇，最后再用脱水剂进行处理，从而得到α-芳香烯。
• [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。
• Process for the preparation of substituted trans-cinnamaldehyde, a natural yellow dye, from phenylpropane derivatives
  申请人：——

  公开号：US20020133045A1

  公开（公告）日：2002-09-19

  The present invention relates to the preparation of substituted trans-cinnamaldehyde, a natural yellow dye from Phenylpropane derivatives having R 2 -R 3 -R 4 -R 5 -R 6 substitution, wherein R 2 to R 6 equal or different, being hydrogen or hydroxy or acyl or halogen or alkyl or heterocyclic or aryl or dioxymethylene or alkoxy groups, etc., by oxidizing the said phenylpropane derivatives using a oxidising agent such as 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) or p-chloranil or pyridinium chlorochromate (PCC) or tBuOOH or or CrO 3 with a catalytic amount of inorganic/organic acid or alumina, celite, and silica gel as a solid support for microwave irradiation and thus substituted trans-cinnamaldehydes, a natural yellow dye, are obtained in high yield ranging from 68-82%.

  本发明涉及制备取代的反式肉桂醛，一种从苯丙烷衍生物中具有R2-R3-R4-R5-R6取代的天然黄色染料，其中R2到R6相等或不同，是氢、羟基、酰基、卤素、烷基、杂环、芳基、二氧甲基或烷氧基等基团，通过使用氧化剂如2,3-二氯-5,6-二氰基-1,4-苯醌（DDQ）或对氯苯醌或氯铬酸吡啶盐（PCC）或tBuOOH或CrO3以及无机/有机酸或氧化铝、硅藻土和硅胶等固体支撑体进行微波辐射，从而高产率地获得取代的反式肉桂醛，一种天然黄色染料，产率范围为68-82%。