2,6-dimethoxy-3-methylbenzoic acid | 96897-96-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,6-dimethoxy-3-methylbenzoic acid
• 英文别名: 2,6-dimethoxy-3-methyl-benzoic acid；2,6-Dimethoxy-3-methyl-benzoesaeure
• CAS: 96897-96-0
• 化学式: C₁₀H₁₂O₄
• 分子量: 196.203
• InChiKey: FZXXCOREGQDGHV-UHFFFAOYSA-N

物化性质

• 熔点：
  146-147 °C
• 沸点：
  322.8±37.0 °C(Predicted)
• 密度：
  1.180±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,6-dimethoxy-3-methylbenzoic acid 在 盐酸 、 氯化亚砜 、 三溴化硼 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 、 氯仿 、 甲苯 为溶剂， 反应 2.0h， 生成 N-[[(2S)-1-ethylpyrrolidin-2-yl]methyl]-6-hydroxy-2-methoxy-3-methylbenzamide
  参考文献：
  名称：

  Potential neuroleptic agents. 3. Chemistry and antidopaminergic properties of substituted 6-methoxysalicylamides

  摘要：

  A series of substituted 6-methoxysalicylamides were synthesized from their corresponding 2,6-dimethoxybenzamides by demethylation of one methoxy group with boron tribromide. Substituted 6-methoxysalicylamides having a lipophilic aromatic substituent in the 3-position para with respect to the methoxy group, e.g. a bromo or an iodo atom or an ethyl or a propyl group, and having an (S)-N-(1-alkyl-2-pyrrolidinyl)methyl moiety as the side chain were found to be potent blockers of [3H]spiperone binding in vitro and potent inhibitors of the apomorphine syndrome in the rat. Similar to remoxipride but in contrast to haloperidol, some of the substituted salicylamides show a 10-20-fold separation between the dose that inhibits hyperactivity and that which inhibits stereotypy. It was concluded that, besides the requirement of a lipophilic substituent in the position para to the methoxy group for antidopamine activity in vivo, the formation of a coplanar six-membered pseudoring involving the amide moiety and the methoxy group is a structural requirement for activity in vitro.

  DOI：

  10.1021/jm00147a025
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 alkaline aqueous sodium hypochlorite solution 作用下， 生成 2,6-dimethoxy-3-methylbenzoic acid
  参考文献：
  名称：

  柠檬素的化学；2，4-二甲氧基-3-乙基苯甲酸和2，6-二甲氧基-3-甲基苯甲酸的合成。

  摘要：

  DOI：

  10.1021/jo01172a013

文献信息

• Potential neuroleptic agents. 4. Chemistry, behavioral pharmacology, and inhibition of [3H]spiperone binding of 3,5-disubstituted N-[(1-ethyl-2-pyrrolidinyl)methyl]-6-methoxysalicylamides
  作者：Tomas De Paulis、Yatendra Kumar、Lars Johansson、Sten Raemsby、Haakan Hall、Maria Saellemark、Kristina Aengeby-Moeller、Sven Ove Oegren

  DOI：10.1021/jm00151a010

  日期：1986.1

  methyl]-6-methoxysalicylamides was synthesized, starting from the 2,6-dimethoxybenzoic acids, by boron tribromide demethylation of the corresponding 3,5-disubstituted 2,6-dimethoxybenzamides and separation of the two positional isomers. The correct structure assignments were based on selective decoupling studies on their 13C NMR spectra. The salicylamide derivatives were tested for antidopamine activity in vivo

  从2,6-二甲氧基苯甲酸开始，通过相应的3,5-硼的三溴化硼脱甲基，合成了一系列的3,5-二取代的N-[（（1-乙基-2-吡咯烷基）甲基] -6-甲氧基水杨酰胺。二取代2，6-二甲氧基苯甲酰胺和两个位置异构体的分离。正确的结构分配基于对它们的13C NMR光谱进行的选择性去偶联研究。水杨酰胺衍生物通过在大鼠中抑制阿扑吗啡综合征的能力在体内进行了抗多巴胺活性的测试，并在体外从大鼠脑纹状体制剂中置换了[3H]哌酮的能力进行了体外抗多巴胺活性的测试。该活性似乎仅存在于S对映异构体中。几种化合物比氟哌啶醇更有效，特别是在芳环的3-位具有乙基且在5-位具有卤原子的那些。相应的5-烷基-3-卤素取代的化合物的活性低得多。发现最有效的化合物的急性毒性低。一些水杨酰胺在阻止阿扑吗啡诱导的过度活跃和阻止阿朴吗啡引起的刻板印象的剂量之间显示出10-20倍的间隔。一种化合物S-（-）-3,5-二氯-N-[（（1-乙基-2-吡咯烷基）甲基]
• Direct Site-Selective Arylation of Enamides via a Decarboxylative Cross-Coupling Reaction
  作者：Nicolas Gigant、Laëtitia Chausset-Boissarie、Isabelle Gillaizeau

  DOI：10.1021/ol303497q

  日期：2013.2.15

  An efficient Pd-catalyzed decarboxylative cross-coupling reaction of simple enamides was achieved. Depending on the choice of the nitrogen-protecting group, a site-selective synthesis of mono- or diarylated framework(s) was performed under mild conditions. This unprecedented reactivity could be applied to the synthesis of a range of 2- or 2,4-diarylated nitrogen-containing bioactive derivatives.

  实现了简单的酰胺的高效Pd催化的脱羧交叉偶联反应。根据氮保护基的选择，在温和条件下进行单-或二芳基构架的位点选择性合成。这种空前的反应性可用于合成一系列2-或2,4-二芳基化的含氮生物活性衍生物。
• The first total synthesis of pyralomicin 2c
  作者：Kuniaki Tatsuta、Masaaki Takahashi、Noboru Tanaka

  DOI：10.1016/s0040-4039(99)00046-5

  日期：1999.3

  Pyralomicin 2c (2) has been synthesized by N-glucosylation of the aglycone 16, which was prepared from the appropriately substituted pyrrole and benzoyl chloride (5 and 9). (C) 1999 Elsevier Science Ltd. All rights reserved.
• PAULIS, T. DE;KUMAR, YATENDRA;JOHANSSON, L.;RAEMSBY, S.;FLORVALL, L.;HALL+, J. MED. CHEM., 1985, 28, N 9, 1263-1269
  作者：PAULIS, T. DE、KUMAR, YATENDRA、JOHANSSON, L.、RAEMSBY, S.、FLORVALL, L.、HALL+

  DOI：——

  日期：——
• DE, PAULIS, T.;KUMAR, YATENDRA;JOHANSSON, L.;RAEMSBY, S.;HALL, H.;SAELLEM+, J. MED. CHEM., 1986, 29, N 1, 61-69
  作者：DE, PAULIS, T.、KUMAR, YATENDRA、JOHANSSON, L.、RAEMSBY, S.、HALL, H.、SAELLEM+

  DOI：——

  日期：——