(E)-1,2,3-trimethoxy-5-(3-methylbut-1-en-1-yl)benzene | 1564262-05-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (E)-1,2,3-trimethoxy-5-(3-methylbut-1-en-1-yl)benzene
• 英文别名: (E)-1,2,3-trimethoxy-5-(3-methylbut-1-enyl)benzene；1,2,3-trimethoxy-5-[(E)-3-methylbut-1-enyl]benzene
• CAS: 1564262-05-0
• 化学式: C₁₄H₂₀O₃
• 分子量: 236.311
• InChiKey: ICYCKKZWLBNIMR-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  2,2-二甲基-2,6-二氢-吡喃并[3,2-c]喹啉-5-酮 、 (E)-1,2,3-trimethoxy-5-(3-methylbut-1-en-1-yl)benzene 以 neat (no solvent) 为溶剂， 反应 16.0h， 以12%的产率得到(1RS,2RS,2aRS,10aSR)-1,10,10-trimethyl-2-(3,4,5-trimethoxyphenyl)-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-Methyl-1-(3,4,5-trimethoxyphenyl)butan-1-ol 在 silica gel 作用下， 以 1,4-二氧六环 为溶剂， 生成 (E)-1,2,3-trimethoxy-5-(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

• Copper-Catalyzed Decarboxylative C(sp² )-C(sp³ ) and C(sp)-C(sp³ ) Coupling of Substituted Cinnamic Acids and 3-Phenyl Propiolic Acid with N-Tosyl Oxaziridines
  作者：Bich-Ngoc Nguyen、Hai-Thuong Cao

  DOI：10.1002/ejoc.201900982

  日期：2019.9.15

  We describe the copper‐catalyzed decarboxylative alkylation of substituted cinnamic acids using N‐Tosyl oxaziridines with high yields and excellent stereoselectivities. The (E)‐alkene was achieved as the sole isomer in a single step. Our protocol also gives an efficient approach for the construction of alkyl phenyl acetylenes without oxidants and bases. Initial investigation suggested a radical process

  我们描述了使用N-甲苯磺酰氧氮丙啶具有高收率和优异的立体选择性的铜催化的取代肉桂酸脱羧烷基化反应。（E）-烯烃是一步完成的唯一异构体。我们的协议还为构建没有氧化剂和碱的烷基苯基乙炔提供了一种有效的方法。初步调查表明，涉及到一个激进的过程。
• a-ASARY-LALDEHYDE ESTER, PREPARATION METHOD THEREFOR, AND APPLICATION THEREOF
  申请人：NORTHWEST UNIVERSITY

  公开号：US20170260122A1

  公开（公告）日：2017-09-14

  The present invention relates to α-asary-laldehyde ester, a preparation method therefor, and an application thereof. The chemical structure of the related α-asary-laldehyde ester is represented by formula I. A related application is an application of the compound in preparation of drugs for calming, mind tranquillizing, senile dementia resisting, convulsion resisting, epilepsy resisting and depression resisting.

  本发明涉及α-沙尼醛酯、其制备方法及其应用。相关α-沙尼醛酯的化学结构由式I表示。相关应用是将该化合物用于制备镇静、安神、抗老年性痴呆、抗惊厥、抗癫痫和抗抑郁药物。
• Inhibitors of Histone Deacetylase
  申请人：Moradei Oscar

  公开号：US20080132459A1

  公开（公告）日：2008-06-05

  The invention relates to the inhibition of histone deacetylase. The invention provides compounds and methods for inhibiting histone deacetylase enzymatic activity. The invention also provides compositions and methods for treating cell proliferative diseases and conditions.

  本发明涉及抑制组蛋白去乙酰化酶的方法。本发明提供了抑制组蛋白去乙酰化酶酶活性的化合物和方法。本发明还提供了用于治疗细胞增殖性疾病和病状的组合物和方法。
• COMPOUNDS AS ANTI-MALARIALS AND THEIR PROCESS OF PREPARATION
  申请人：Council of Scientific and Industrial Research

  公开号：EP3209639B1

  公开（公告）日：2020-09-16
• Aromatic Derivatives As Anti-Malarial
  申请人：Council of Scientific & Industrial Research

  公开号：US20190106380A1

  公开（公告）日：2019-04-11

  The present invention discloses anti-malarial compound of formula (I) Formula (I) wherein, X is selected from O or NH; R 1 , R 2 , R 3 , R 4 and R 5 is selected from H or OMe or CH 3 , —CH 2 —O—CH 2 — or —CH═CH—CH═CH—; Y is selected from O or NH and R 6 , R 7 is selected from the following compounds: or pharmaceutically acceptable salts thereof, process for preparation and a pharmaceutical composition containing the same.