3-methoxy-4-(pivaloyloxy)benzoic acid | 122665-61-6

• 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: 3-methoxy-4-(pivaloyloxy)benzoic acid
• 英文别名: 4-O-pivaloylvanillic acid；4-(2,2-dimethylpropanoyloxy)-3-methoxybenzoic acid
• CAS: 122665-61-6
• 化学式: C₁₃H₁₆O₅
• 分子量: 252.267
• InChiKey: CYMGBFZOQMAKRL-UHFFFAOYSA-N

物化性质

• 溶解度：
  二氯甲烷；

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-methoxy-4-(pivaloyloxy)benzoic acid 在 磺酰氯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 4-O-pivaloylvanilloyl chloride
  参考文献：
  名称：

  A Regiodivergent Synthesis of Ring A C-Prenylflavones

  摘要：

  Capitalizing on the use of orthogonal protecting groups and the development of a modified Robinson flavone synthesis that avoids harsh acidic conditions, a regioselective synthesis of 6- and 8-prenylflavones from the same prenylated disilylated phloracetophenone (9) has been developed, targeting cannflavin B (1d), the COX-inhibiting principle of marijuana, and its unnatural isomer isocannflavin B (1e) as model compounds.

  DOI：

  10.1021/ol800665w
• 作为产物：
  描述：

  香草酸 、 三甲基乙酰氯 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 水 为溶剂， 反应 5.0h， 以100%的产率得到3-methoxy-4-(pivaloyloxy)benzoic acid
  参考文献：
  名称：

  Hemisynthesis, Antitumoral Effect, and Molecular Docking Studies of Ferutinin and Its Analogues

  摘要：

  The natural product ferutinin was shown to act as an agonist to estrogen receptor ERα and agonist/antagonist to ERβ featuring a weak antiproliferative activity toward breast cancer cells. To enhance this activity, ferutinin analogues were synthesized by esterification of jaeschkenadiol with different acids. These compounds were assayed for their in vitro antiproliferative activity against estrogen‐dependent (MCF‐7) and estrogen‐independent (MDA‐MB‐231) breast cancer cell lines. Among the compounds, 3c’ exhibited a potent inhibitory selective activity against MCF‐7 with IC50 value of 1 μm. Docking simulation of 3c’ in the ligand binding domain of the ERs indicated a potential antagonism interaction with both ER subtypes. Functional assay showed that 3c’ binds as an antagonist to ERα protein while ferutinin acts as an agonist.

  DOI：

  10.1111/cbdd.12670

文献信息

• Benzine derivatives, process for preparing the same and use thereof
  申请人：——

  公开号：US20040259912A1

  公开（公告）日：2004-12-23

  Novel benzene derivatives represented by the formula (I): 1 wherein R 1 , R 4 and R 6 each independently represents a hydrogen atom, a halogen atom or a hydrocarbon group, R 2 represents a hydrocarbon group or a heterocyclic group, R 3 represents a hydrocarbon group, NR 7′ R 7 or OR 8 (wherein R 7′ represents a hydrogen atom or a hydrocarbon group, R 7 represents a non-aromatic group, or R 7′ and R 7 may form a ring with the adjacent nitrogen atom, and R 8 represents a hydrocarbon group or a heterocyclic group), R 5 represents a hydrocarbon group or a heterocyclic group (except for a quinolyl group), R 5′ represents a hydrogen atom, or a hydrocarbon group, or R 5 and R 5′ may form a ring with the adjacent nitrogen atom, and R 5″ represents a hydrogen atom or a hydrocarbon group, which have vanilloid receptor agonist activity and are useful as a drug such as an analgesic and an agent for preventing and/or treating urinary frequency and/or urinary incontinence.

  式(I)所表示的新型苯衍生物，其中R1、R4和R6各自独立地表示氢原子、卤素原子或烃基，R2表示烃基或杂环基，R3表示烃基、NR7′R7或OR8（其中R7′表示氢原子或烃基，R7表示非芳香族基团，或R7′和R7可与相邻的氮原子形成环，R8表示烃基或杂环基），R5表示烃基或杂环基（除了喹啉基团），R5′表示氢原子或烃基，或R5和R5′可与相邻的氮原子形成环，R5″表示氢原子或烃基，具有vanilloid受体激动剂活性，并且可用作药物，例如镇痛剂和预防和/或治疗尿频和/或尿失禁的药剂。
• BENZENE DERIVATIVES,PROCESS FOR PREPARING THE SAME AND USE THEREOF
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP1437344A1

  公开（公告）日：2004-07-14

  Novel benzene derivatives represented by the formula (I) : wherein R1, R4 and R6 each independently represents a hydrogen atom, a halogen atom or a hydrocarbon group, R2 represents a hydrocarbon group or a heterocyclic group, R3 represents a hydrocarbon group, NR7'R7 or OR8 (wherein R7' represents a hydrogen atom or a hydrocarbon group, R7 represents a non-aromatic group, or R7' and R7 may form a ring with the adjacent nitrogen atom, and R8 represents a hydrocarbon group or a heterocyclic group), R5 represents a hydrocarbon group or a heterocyclic group (except for a quinolyl group), R5' represents a hydrogen atom, or a hydrocarbon group, or R5 and R5' may form a ring with the adjacent nitrogen atom, and R5" represents a hydrogen atom or a hydrocarbon group, which have vanilloid receptor agonist activity and are useful as a drug such as an analgesic and an agent for preventing and/or treating urinary frequency and/or urinary incontinence.

  由式(I)代表的新型苯衍生物： 其中 R1、R4 和 R6 各自独立地代表氢原子、卤素原子或烃基，R2 代表烃基或杂环基，R3 代表烃基、NR7'R7 或 OR8（其中 R7'代表氢原子或烃基，R7 代表非芳香族基团，或 R7'和 R7 可与相邻的氮原子形成环，R8 代表烃基或杂环基）、R5代表烃基或杂环基（喹啉基除外），R5'代表氢原子或烃基，或 R5和R5'可与相邻的氮原子形成环，R5 "代表氢原子或烃基，它们具有香兰素受体激动剂活性，可用作药物，如镇痛剂和预防和/或治疗尿频和/或尿失禁的药物。
• Ru(II)-Catalyzed Divergent C–H Alkynylation Cascade with Bifunctional α-Alcohol Haloalkynes
  作者：Qiaoya Zhang、Yinling Li、Yabo Chen、Jiahua Jiang、Yuan Liu、Jiye Luo、Yang Gao、Yanping Huo、Qian Chen、Xianwei Li

  DOI：10.1021/acs.orglett.4c00283

  日期：2024.3.22

  directed the C–H activation cascade to enable rapid construction of molecular complexity, featuring step-economy and synthetic efficiency. Herein, by exploiting bifunctional α-alcohol haloalkynes, we developed Ru(II)-catalyzed carboxylic acid, amine, and amide assisted divergent C–H alkynylation and annulation cascade, affording polyfunctional heterocycles. Significantly, a bilateral aryl C–H polycyclization

  天然功能指导 C-H 激活级联，以实现分子复杂性的快速构建，具有步骤经济性和合成效率。在此，通过利用双官能α-醇卤代炔，我们开发了Ru(II)催化的羧酸、胺和酰胺辅助的发散C-H炔基化和环化级联，得到多官能杂环。值得注意的是，使用多功能卤代炔实现了偶氮苯的双边芳基C-H多环化级联。
• Hemisynthesis, Antitumoral Effect, and Molecular Docking Studies of Ferutinin and Its Analogues
  作者：Rémi Safi、Fréderic Rodriguez、Georges Hilal、Mona Diab-Assaf、Youssef Diab、Marwan El-Sabban、Fadia Najjar、Evelyne Delfourne

  DOI：10.1111/cbdd.12670

  日期：2016.3

  The natural product ferutinin was shown to act as an agonist to estrogen receptor ERα and agonist/antagonist to ERβ featuring a weak antiproliferative activity toward breast cancer cells. To enhance this activity, ferutinin analogues were synthesized by esterification of jaeschkenadiol with different acids. These compounds were assayed for their in vitro antiproliferative activity against estrogen‐dependent (MCF‐7) and estrogen‐independent (MDA‐MB‐231) breast cancer cell lines. Among the compounds, 3c’ exhibited a potent inhibitory selective activity against MCF‐7 with IC50 value of 1 μm. Docking simulation of 3c’ in the ligand binding domain of the ERs indicated a potential antagonism interaction with both ER subtypes. Functional assay showed that 3c’ binds as an antagonist to ERα protein while ferutinin acts as an agonist.
• A Regiodivergent Synthesis of Ring A C-Prenylflavones
  作者：Alberto Minassi、Anna Giana、Abdellah Ech-Chahad、Giovanni Appendino

  DOI：10.1021/ol800665w

  日期：2008.6.5

  Capitalizing on the use of orthogonal protecting groups and the development of a modified Robinson flavone synthesis that avoids harsh acidic conditions, a regioselective synthesis of 6- and 8-prenylflavones from the same prenylated disilylated phloracetophenone (9) has been developed, targeting cannflavin B (1d), the COX-inhibiting principle of marijuana, and its unnatural isomer isocannflavin B (1e) as model compounds.