1,2,4-三甲氧基-5-丙基-苯 | 6906-65-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1,2,4-三甲氧基-5-丙基-苯
• 英文名称: 1-propyl-2,4,5-trimethoxybenzene
• 英文别名: Dihydroasarone；1-(2',4',5'-trimethoxyphenyl)propane；1-(2,4,5-trimethoxyphenyl)propane；3-(2,4,5-trimethoxyphenyl)propane；2,4,5-trimethoxyphenylpropane；Benzene, 1,2,4-trimethoxy-5-propyl-；1,2,4-trimethoxy-5-propylbenzene
• CAS: 6906-65-6
• 化学式: C₁₂H₁₈O₃
• 分子量: 210.273
• InChiKey: SNDHRSZUZCBJPB-UHFFFAOYSA-N

物化性质

• 沸点：
  114 °C(Press: 2 Torr)
• 密度：
  0.997±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,2,4-三甲氧基-5-丙基-苯 在 溶剂黄146 、 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 2.0h， 以82%的产率得到2-丙烯醛,3-(2,4,5-三甲氧苯基)-
  参考文献：
  名称：

  Efficient one-pot, two-step synthesis of (E)-cinnmaldehydes by dehydrogenation–oxidation of arylpropanes using DDQ under ultrasonic irradiation

  摘要：

  A general, efficient and new approach to the synthesis of cinnamaldehydes with trans-selectivity has been accomplished starting from arylpropanes. One-pot, two-step dehydrogenation and oxidation of arylpropanes with excess DDQ in dioxane containing a few drops of acetic acid gave (E)-cinnmaldehydes under ultrasound irradiation. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.12.028
• 作为产物：
  描述：

  1,2,4-三甲氧基-5-丙-2-烯基苯 在 palladium on activated charcoal 氢气 作用下， 生成 1,2,4-三甲氧基-5-丙基-苯
  参考文献：
  名称：

  Devgan,O.N.; Bokadia,M.M., Australian Journal of Chemistry, 1968, vol. 21, p. 3001 - 3003

  摘要：

  DOI：

文献信息

• Larvicidal and Structure-Activity Studies of Natural Phenylpropanoids and Their Semisynthetic Derivatives against the Tobacco Armyworm<i>Spodoptera litura</i>(Fab.) (Lepidoptera: Noctuidae)
  作者：Anu Bhardwaj、Dhananjay Kumar Tewary、Rakesh Kumar、Vinod Kumar、Arun Kumar Sinha、Adarsh Shanker

  DOI：10.1002/cbdv.200800345

  日期：2010.1

  The larvicidal activity of 18 phenylpropanoids, 1-18, including phenylpropenoate, phenylpropenal, phenylpropene, and their semisynthetic analogues, were evaluated against the tobacco armyworm, Spodoptera litura (Fab.), to identify promising structures with insecticidal activity. Amongst various phenylpropanoids, isosafrole, a phenylpropene, showed the best activity, with an LC(50) value of 0.6 microg/leaf

  评估了18个苯基丙烷（1-18）的杀幼虫活性（包括苯基丙酸酯，苯基丙烯醛，苯基丙烯及其半合成类似物）对烟草粘虫Spodoptera litura（Fab。）的杀虫活性，以鉴定具有杀虫活性的有前途的结构。在各种苯丙类化合物中，异黄酮（一种苯丙烯）表现出最好的活性，其LC（50）值为0.6微克/叶cm（2），其次是其氢化衍生物二氢黄樟脑（LC（50）= 2.7微克/叶cm（2 ））。按以下顺序观察到各种苯丙烯衍生物的整体杀幼虫活性：异黄樟脑（6）>二氢黄樟脑（16）>黄樟脑（12）>茴香脑（4）>甲基丁香酚（11）>丁香酚（13）>β-asarone（ 8）>二氢asarone（18）>二氢茴香脑（15）。二氢黄樟脑可能是很有前途的化合物，尽管其杀幼虫活性低于异黄酮，但由于其稳定性和抗氧化降解性（由于去除了极活泼的烯键），与异黄酮相比具有更好的稳定性。这种结构-活性关系研究促进了从天然来源鉴定
• Development of microchannel reactors using polysilane-supported palladium catalytic systems in capillaries
  作者：Masaharu Ueno、Toshie Suzuki、Takeshi Naito、Hidekazu Oyamada、Shū Kobayashi

  DOI：10.1039/b715259k

  日期：——

  A new method of immobilizing Pd catalysts on the channel wall of a capillary by using polysilane with metal oxide has been developed, and applied to hydrogenation reactions.

  一种新的方法已被开发，通过使用含有金属氧化物的聚硅烷，在毛细管的通道壁上固定钯催化剂，并已应用于加氢反应。
• Potential antipsychotic agents. 5. Synthesis and antidopaminergic properties of substituted 5,6-dimethoxysalicylamides and related compounds
  作者：Thomas Hoegberg、Stefan Bengtsson、Tomas De Paulis、Lars Johansson、Peter Stroem、Haakan Hall、Sven Ove Oegren

  DOI：10.1021/jm00166a012

  日期：1990.4

  assessed by studies of the related amino analogues 23 and 24 and hydroxy analogue 27. The 3-bromo compound 11 (FLB 463) was studied in various in vivo models and compared with the dopamine-D2 antagonists sulpiride, raclopride, eticlopride, and haloperidol. The high potency of 11 to selectively block dopamine-D2 receptors in vitro and in vivo combined with indications on a low potential for motor side effects

  由相应的2,5,6-三甲氧基苯甲酸合成了一系列3-取代的5,6-二甲氧基水杨酰胺III（9-13和15）。III中甲氧基的弛豫时间T1和碳的化学位移表明，6-甲氧基相对于溶液中的环平面呈几乎垂直的取向，而5-甲氧基相对于环平面呈更共面的取向。在体外，水杨酰胺III对[3H]哌酮和[3H] raclopride结合位点显示出很高的立体选择性亲和力。区域异构的水杨酰胺IV对[3H] spiperone结合位点也显示出明显但低于III的亲和力。通过研究相关的氨基类似物23和24和羟基类似物27进一步评估了结构要求。在各种体内模型中研究了3-溴化合物11（FLB 463），并将其与多巴胺D2拮抗剂舒必利，雷洛必利，依替普利和氟哌啶醇进行了比较。11在体外和体内选择性阻断多巴胺D2受体的高效力以及对运动副作用的潜在可能性较低的迹象使其成为取代水杨酰胺类中非常有趣的新成员。
• 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。