(E)-1,2-dimethoxy-4-(3-methylbut-1-en-1-yl)benzene | 195192-74-6

• 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: (E)-1,2-dimethoxy-4-(3-methylbut-1-en-1-yl)benzene
• 英文别名: E-1,2-dimethoxy-4-(3-methylbut-1-en-1-yl)benzene；(E)-1,2-dimethoxy-4-(3-methylbut-1-enyl)benzene；1,2-dimethoxy-4-[(E)-3-methylbut-1-enyl]benzene
• CAS: 195192-74-6
• 化学式: C₁₃H₁₈O₂
• 分子量: 206.285
• InChiKey: YQUHGKSIEWKODT-AATRIKPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-1,2-dimethoxy-4-(3-methylbut-1-en-1-yl)benzene 、 haplamine 以 neat (no solvent) 为溶剂， 反应 16.0h， 以16%的产率得到(1RS,2RS,2aRS,10aSR)-7-methoxy-10,10-dimethyl-1-(1-methylethyl)-2-(3,4-dimethoxyphenyl)-1,2,2a,4,10,10a-hexahydro-3H-cyclobuta[4,5]pyrano[3,2-c]quinolin-3-one
  参考文献：
  名称：

  Euodenine A: A Small-Molecule Agonist of Human TLR4

  摘要：

  A small-molecule natural product, euodenine A (1), was identified as an agonist of the human TLR4 receptor. Euodenine A was isolated from the leaves of Euodia asteridula (Rutaceae) found in Papua New Guinea and has an unusual U-shaped structure. It was synthesized along with a series of analogues that exhibit potent and selective agonism of the TLR4 receptor. SAR development around the cyclobutane ring resulted in a 10-fold increase in potency. The natural product demonstrated an extracellular site of action, which requires the extracellular domain of TLR4 to stimulate a NF-kappa B reporter response. 1 is a human-selective agonist that is CD14-independent, and it requires both TLR4 and MD-2 for full efficacy. Testing for immunomodulation in PBMC cells shows the induction of the cytokines IL-8, IL-10, TNF-alpha, and IL-12p40 as well as suppression of IL-5 from activated PBMCs, indicating that compounds like 1 could modulate the Th2 immune response without causing lung damage.

  DOI：

  10.1021/jm401321v
• 作为产物：
  描述：

  3,4-二甲氧基苯甲醛 在 silica gel 作用下， 以 1,4-二氧六环 、 乙醚 、 甲苯 为溶剂， 反应 16.0h， 生成 (E)-1,2-dimethoxy-4-(3-methylbut-1-en-1-yl)benzene
  参考文献：
  名称：

  Euodenine A: A Small-Molecule Agonist of Human TLR4

  摘要：

  A small-molecule natural product, euodenine A (1), was identified as an agonist of the human TLR4 receptor. Euodenine A was isolated from the leaves of Euodia asteridula (Rutaceae) found in Papua New Guinea and has an unusual U-shaped structure. It was synthesized along with a series of analogues that exhibit potent and selective agonism of the TLR4 receptor. SAR development around the cyclobutane ring resulted in a 10-fold increase in potency. The natural product demonstrated an extracellular site of action, which requires the extracellular domain of TLR4 to stimulate a NF-kappa B reporter response. 1 is a human-selective agonist that is CD14-independent, and it requires both TLR4 and MD-2 for full efficacy. Testing for immunomodulation in PBMC cells shows the induction of the cytokines IL-8, IL-10, TNF-alpha, and IL-12p40 as well as suppression of IL-5 from activated PBMCs, indicating that compounds like 1 could modulate the Th2 immune response without causing lung damage.

  DOI：

  10.1021/jm401321v

文献信息

• A transition-metal-free Heck-type reaction between alkenes and alkyl iodides enabled by light in water
  作者：Wenbo Liu、Lu Li、Zhengwang Chen、Chao-Jun Li

  DOI：10.1039/c5ob00515a

  日期：——

  A transition-metal-free coupling protocol between various alkenes and non-activated alkyl iodides has been developed by using photoenergy in water for the first time. Under UV irradiation and basic aqueous conditions, various alkenes efficiently couple with a wide range of non-activated alkyl iodides. A tentative mechanism, which involves an atom transfer radical addition process, for the coupling

  首次通过在水中使用光能，开发了各种烯烃与未活化烷基碘之间的无过渡金属偶联方案。在紫外线辐射和碱性水溶液条件下，各种烯烃与各种未活化的烷基碘有效地偶联。提出了一种涉及原子转移自由基加成过程的偶合机理。
• Low‐Pressure Cobalt‐Catalyzed Enantioselective Hydrovinylation of Vinylarenes
  作者：Sohajl Movahhed、Julia Westphal、Mehmet Dindaroğlu、Anna Falk、Hans‐Günther Schmalz

  DOI：10.1002/chem.201601283

  日期：2016.5.23

  An efficient and practical protocol for the enantioselective cobalt‐catalyzed hydrovinylation of vinylarenes with ethylene at low (1.2 bar) pressure has been developed. As precatalysts, stable [L2CoCl2] complexes are employed that are activated in situ with Et2AlCl. A modular chiral TADDOL‐derived phosphine–phosphite ligand was identified that allows the conversion of a broad spectrum of substrates

  已经开发了一种有效且实用的方案，用于在低压（1.2 bar）压力下用乙烯对乙烯进行对映选择性钴催化的乙烯基乙烯基氢化乙烯基化。作为预催化剂，使用了稳定的[L 2 CoCl 2 ]络合物，该络合物被Et 2 AlCl原位活化。鉴定出一种模块化手性TADDOL衍生的膦-亚磷酸酯配体，该配体可以转化包括杂环乙烯基芳烃和乙烯基二茂铁在内的各种底物，从而为支链产物提供99％ee和几乎完全的区域选择性。即使极性官能团，如OH，NH 2，CN和CO 2 R，是容许的。
• PROCESS FOR PREPARING NITROOXYALKYL SUBSTITUTED ESTERS OF CARBOXYLIC ACIDS, INTERMEDIATES USEFUL IN SAID PROCESS AND PREPARATION THEREOF
  申请人：DEL SOLDATO Piero

  公开号：US20100217028A1

  公开（公告）日：2010-08-26

  The present invention refers to a process for preparing a compound of general formula (A), as reported in the description, wherein R is a radical of a drug and R1-R12 are hydrogen or alkyl groups, m, n, o, q, r and s are each independently an integer from 0 to 6, and p is 0 or 1, and X is O, S, SO, SO2, NR13 or PR13 or an aryl, heteroaryl group, said process comprising reacting a compound of formula (B) R—COOZ (B) wherein R is as defined above and Z is hydrogen or a cation selected from: Li+, Na+, K+, Ca++, Mg++, tetralkylammonium, tetralkylphosphonium, with a compound of formula (C), as reported in the description, wherein R1-R12 and m, n, o, p, q, r, s are as defined above and Y is a suitable leaving group.

  本发明涉及一种制备一般式（A）化合物的过程，如描述所述，其中R是药物的基团，R1-R12是氢或烷基，m，n，o，q，r和s分别独立地为0至6的整数，p为0或1，X为O，S，SO，SO2，NR13或PR13或芳基，杂环基，所述过程包括反应一种化合物的公式（B）R-COOZ（B），其中R如上定义，Z为氢或选自：Li+，Na+，K+，Ca++，Mg++，四烷基铵，四烷基膦的阳离子，与一种公式（C）的化合物，如描述所述，其中R1-R12和m，n，o，p，q，r，s如上定义，Y是适当的离去基团。
• Anti-Inflammatory Compounds and Uses Thereof
  申请人：MEDICON PHARMACEUTICALS, INC.

  公开号：US20190307780A1

  公开（公告）日：2019-10-10

  Compounds of the general formula are disclosed with activity towards treating diseases related to inflammation, such as cancer, neurodegenerative and cardiovascular diseases. Pharmaceutical compositions and methods of use are also described.
• MATTER OF COMPOSITION, SYNTHESIS, FORMULATION AND APPLICATION OF FL118 PLATFORM POSITIONS 7 AND 9-DERIVED ANALOGUES FOR TREATMENT OF HUMAN DISEASE
  申请人：Canget BioTekpharma

  公开号：US20200231596A1

  公开（公告）日：2020-07-23

  Described herein, are the chemical synthesis, matter of compositions, formulation, function, methods and uses of the FL118 platform Positions 7 and/or 9-derived analogues for treating cancer or other human diseases. Compounds derived from chemical modifications of the FL118 platform are employed alone or in combination with other anti-cancer agents to preclude, eliminate or reverse cancer phenotypes. This invention intends to realize unique personalized cancer treatment (personalized precision medicine) through application of a series of structural relevant individual FL118 platform-derived analogues, which target multiple cellular human disease-relevant proteins and their signaling pathways.