6-methoxy-benzo[1,3]dioxole-5-carboxylic acid | 7168-93-6

• 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: 6-methoxy-benzo[1,3]dioxole-5-carboxylic acid
• 英文别名: 2-methoxy-4,5-(methylenedioxy)benzoic acid；3,4-methylenedioxy-6-methoxybenzoic acid；6-Methoxy-benzo[1,3]dioxol-5-carbonsaeure；6-methoxy-1,3-benzodioxole-5-carboxylic acid；2-Methoxy-4,5-methylendioxy-benzoesaeure；6-Methoxy-3,4-methylendioxy-benzoesaeure；1,3-Benzodioxole-5-carboxylic acid, 6-methoxy-
• CAS: 7168-93-6
• 化学式: C₉H₈O₅
• mdl: MFCD16061365
• 分子量: 196.16
• InChiKey: KISJQBUVHAHZFD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-methoxy-benzo[1,3]dioxole-5-carboxylic acid 在 盐酸 、 氢氧化钾 、 正丁基锂 、 磺酰氯 、 草酰氯 、 双(三甲基硅基)过氧化物 、 1,1,2,2-四氟-1,2-二溴乙烷 、 magnesium 作用下， 以 二甲基亚砜 为溶剂， 反应 14.0h， 生成 2-[4-(1-benzyl-2,3-dihydroindol-7-yl)-6-methoxy-1,3-benzodioxol-5-yl]-4,4-dimethyl-5H-1,3-oxazole
  参考文献：
  名称：

  An Oxazoline-Mediated Synthesis of the Pyrrolophenanthridine Alkaloids and Some Novel Derivatives

  摘要：

  An unsymmetrical biaryl coupling between the Grignard of N-benzyl-7-bromoindoline 25 and the appropriately substituted (o-methoxyaryl)oxazoline 15 leads to an intermediate biaryl which can be elaborated in one step to the 1H-pyrrolo[3,2,1-de]phenanthridine ring system. This simple two-step sequence provides general access to the pyrrolophenanthridine alkaloids 2-6.

  DOI：

  10.1021/jo951474x
• 作为产物：
  描述：

  methyl 6-hydroxybenzo[d][1,3]dioxole-5-carboxylate 在 氢氧化钾 、 potassium carbonate 、 苯 作用下， 生成 6-methoxy-benzo[1,3]dioxole-5-carboxylic acid
  参考文献：
  名称：

  Orientation in the 1,3-Benzodioxole Series

  摘要：

  DOI：

  10.1021/ja01226a053

文献信息

• New furofurano lignans from Justicia simplex
  作者：Shibnath Ghosal、Shanta Banerjee、Dinesh K. Jaiswal

  DOI：10.1016/s0031-9422(00)81989-5

  日期：1980.1

  A new 3,7-dioxabicyclo[3,3,O]octane lignan, named justisolin, and a new lignan O-glucoside, named simplexoside, were isolated from the whole plant of Justicia simplex D. Don. (Acanthaceae), collected at fruiting. The structure of the free lignan was established as 2e-(3,4-methylenedioxy-6-hydroxy)-phenyl-6e- Piperonyl-3,7-dioxabicyclo[3,3,0]octane (1) and that of the glucoside as 2e-(3-methoxy-4-O-β-d-

  从 Justicia simplex D. Don 的全株中分离出一种新的 3,7-二氧杂双环 [3,3,O] 辛烷木脂素，命名为 justisolin，以及一种新的木脂素 O-葡萄糖苷，命名为 simplexoside。（Acanthaceae），在结果时收集。游离木脂素的结构确定为 2e-(3,4-methylenedioxy-6-hydroxy)-phenyl-6e- Piperonyl-3,7-dioxabicyclo[3,3,0]octane (1) 和葡萄糖苷的结构作为 2e-(3-甲氧基-4-O-β-d-吡喃葡萄糖基)-苯基-6e-piperonyl-3,7-dioxabicyclo[3,3,0]辛烷 (2) 基于化学转化和光谱证据. 评价了这些和相关木脂素的生物学功能。
• 1,3,8-triaza- and 3,8-diaza-1-oxaspiro \x9b4,5! decane derivatives
  申请人：Syntex (U.S.A.) Inc.

  公开号：US05739336A1

  公开（公告）日：1998-04-14

  Heterocyclic compounds of Formula I: ##STR1## in which n is 2, 3, 4, 5 or 6; t is 1, 2, 3 or 4; u is 0 or 1 (provided that t is not 1 when u is 0); X is O or N(R.sup.4); Y and Z are independently C(O), C(S) or CH.sub.2 (provided that Y and Z are not both CH.sub.2); R.sup.1, R.sup.2, R.sup.3, and R.sup.4 are as defined in the specification; and their pharmaceutically acceptable salts and N-oxides, formulations containing them, their uses as therapeutic agents, and their synthesis.

  公式I的杂环化合物：##STR1##其中n为2、3、4、5或6；t为1、2、3或4；u为0或1（前提是当u为0时，t不是1）；X为O或N(R.sup.4)；Y和Z独立地为C(O)、C(S)或CH.sub.2（前提是Y和Z不同时为CH.sub.2）；R.sup.1、R.sup.2、R.sup.3和R.sup.4如规范中所定义；以及它们的药学上可接受的盐和N-氧化物，含有它们的配方，它们作为治疗剂的用途，以及它们的合成。
• Simonitsch et al., Monatshefte fur Chemie, 1957, vol. 88, p. 541,558
  作者：Simonitsch et al.

  DOI：——

  日期：——
• Identification of the 2-Benzoxazol-2-yl-phenol Scaffold as New Hit for JMJD3 Inhibition
  作者：Assunta Giordano、Giovanni Forte、Stefania Terracciano、Alessandra Russo、Marina Sala、Maria C. Scala、Catrine Johansson、Udo Oppermann、Raffaele Riccio、Ines Bruno、Simone Di Micco

  DOI：10.1021/acsmedchemlett.8b00589

  日期：2019.4.11

  JMJD3 is a member of the KDM6 subfamily and catalyzes the demethylation of lysine 27 on histone H3 (H3K27). This protein was identified as a useful tool in understanding the role of epigenetics in inflammatory conditions and in cancer as well. Guided by a virtual fragment screening approach, we identified the benzoxazole scaffold as a new hit suitable for the development of tighter JMJD3 inhibitors. Compounds were synthesized by a microwave-assisted one-pot reaction under catalyst and solvent-free conditions. Among these, compound 8 presented the highest inhibitory activity (IC50 = 1.22 0.22 /./M) in accordance with molecular modeling calculations. Moreover, 8 induced the cycle arrest in S-phase on A375 melanoma cells.
• CYCLIZATION PROCESS STEP IN THE MAKING OF QUINOLONES AND NAPHTHYRIDINES
  申请人：THE PROCTER & GAMBLE COMPANY

  公开号：EP1343766A1

  公开（公告）日：2003-09-17