6,8-dimethoxy-3-methylisocoumarin | 18110-66-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异香豆素及其衍生物
• 英文名称: 6,8-dimethoxy-3-methylisocoumarin
• 英文别名: 6,8-dimethoxy-3-methyl-1H-isochromen-1-one；6,8-dimethoxy-3-methylisochromen-1-one
• CAS: 18110-66-2
• 化学式: C₁₂H₁₂O₄
• 分子量: 220.225
• InChiKey: JQAXANOEMJLZMG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6,8-dimethoxy-3-methylisocoumarin 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 生成 saccharonol A
  参考文献：
  名称：

  通过哌啶环支架启发枝孢菌素类似物抑制恶性疟原虫赖氨酰-tRNA 合成酶

  摘要：

  本研究重点是针对恶性疟原虫赖氨酰-tRNA 合成酶（ Pf KRS）的哌啶环启发枝孢菌素抑制剂的合成和结构分析。该系列保留了针对人类对应物的选择性，但观察到用哌啶取代四氢吡喃部分会降低效力。 Cla−B 和 Cla−C 与Pf KRS 的共晶揭示了关键的相互作用和环重新调整，从而允许药物结合和抑制酶。

  DOI：

  10.1002/cbic.202100212
• 作为产物：
  描述：

  (2-ethoxycarbonyl-3,5-dimethoxy-phenyl)-acetic acid 在 氢氧化钾 、 甲酸 、 乙醚 、 三氯化磷 作用下， 生成 6,8-dimethoxy-3-methylisocoumarin
  参考文献：
  名称：

  Loss of heterozygosity of the MEN1 gene in a large series of TSH-secreting pituitary adenomas

  摘要：

  Thyrotropin-secreting pituitary adenomas (TSH-omas) are rare tumors (0.5% of all pituitary adenomas) showing an invasive behavior and usually sporadic, although a few cases are associated with multiple endocrine neoplasia type 1 (MEN1), an autosomal dominant inherited syndrome. This disorder is linked to loss of heterozygosity (LOH) on 11q13 and inactivating mutations of MEN1 gene, which is located in the same chromosomal region. As other types of anterior pituitary adenomas, TSH-omas are the result of a monoclonal outgrowth where the intrinsic genetic defects involving oncogenes or tumor suppressor genes occur in a progenitor cell. However, so far no activating mutations of particular oncogenes or inactivating mutations of tumor suppressor genes have been identified. Starting from the observation that 3-30% of sporadic pituitary adenomas show LOH on 11q13, and that allelic losses on the long arms of chromosome 11, beside 10 and 13, are significantly associated with the transition from the non-invasive to the invasive phenotype, we decided to investigate LOH on 11q13 and mutations of menin in a large series of TSH-omas. Thirteen tumors were evaluated. DNA was extracted from tumors by standard methods and genomic DNA from peripheral blood leukocytes was used as control. LOH was screened by using 3 polymorphic markers on 11q13: D11S956, PYGM, INT-2. In 3 out of 15 cases we could demonstrate LOH on 11q13, but none of the tumors showed menin mutation after sequence analysis. These data strongly suggest that menin does not play a causative role in the development of TSH-omas, and are in agreement with other studies demonstrating a limited role of menin in pituitary sporadic tumorigenesis. (C) 2001, Editrice Kurtis.

  DOI：

  10.1007/bf03343929

文献信息

• Asymmetric Synthesis of Natural <i>cis</i>-Dihydroarenediols Using Tetrahydroxynaphthalene Reductase and Its Biosynthetic Implications
  作者：Nirmal Saha、Michael Müller、Syed Masood Husain

  DOI：10.1021/acs.orglett.9b00500

  日期：2019.4.5

  Asymmetric reduction of hydroxynaphthoquinones to secondary metabolites, (3S,4R)-3,4,8- and (2S,4R)-2,4,8-trihydroxy-1-tetralone, a putative biosynthetic diketo intermediate and a probable natural analogue, (3S,4R)-7-acetyl-3,4,8-trihydroxy-6-methyl-3,4-dihydronaphthalene-1(2H)-one, using NADPH-dependent tetrahydroxynaphthalene reductase (T4HNR) of Magnaporthe grisea is described. This work implies

  羟基萘醌不对称还原为次级代谢产物（3 S，4 R）-3,4,8-和（2 S，4 R）-2,4,8-三羟基-1-四氢萘酮，一种假定的生物合成二酮中间体和可能天然类似物，（3小号，4 - [R）-7-乙酰基3,4,8-三羟基-6-甲基-3,4-二氢萘-1（2 ħ） -酮，使用NADPH依赖性羟基萘还原酶（T描述了稻瘟病菌（Magnaporthe grisea）的4 HNR）。这项工作暗示通过减少含羟基萘醌支架的底物，在其他二氢芳烃的（生物）合成过程中，T 4 HNR或相关酶的参与。
• Biosynthesis of fungal metabolites. Terrein, a metabolite of Aspergillus terreus Thom
  作者：Robert A. Hill、Rachel H. Carter、James Staunton

  DOI：10.1039/p19810002570

  日期：——

  Terrein, a metabolite of Aspergillus terreus Thom, is biosynthesised from 3,4-dihydro-6,8-dihydroxy-3-methylisocoumarin by contraction of an aryl ring. The direction of the ring contraction has been investigated using [1,2-13C2]acetate as precursor.

  Terrein是土生曲霉Thom的代谢产物，是通过3,4-二氢-6,8-二羟基-3-甲基异香豆素通过芳基环的缩合生物合成的。该环收缩的方向已经使用[1,2-研究13 Ç 2 ]乙酸甲酯，前体。
• 一种异香豆素芳香醚类化合物的合成方法
  申请人：河南理工大学

  公开号：CN111253358A

  公开（公告）日：2020-06-09

  本发明公开了一种异香豆素芳香醚类化合物的合成方法，属于芳香醚类化合物的合成技术领域，其具体合成路线为：其中R1为C1‑4烷基、苯基或取代苯基，该取代苯基苯环上的取代基为C1‑4烷基、C1‑4烷氧基、卤素或硝基，R2为氢或C1‑4烷基。本发明的合成方法操作简单且目标产物的收率高于之前文献报道的合成收率。
• Reactions of 3-(1-Hydroxyalkyl)phthalides with Acids:  Synthesis of (<i>Z</i>)-3-Alkylidenephthalides and 3-Alkyl-8-hydroxyisocoumarins
  作者：Raghao S. Mali、Kantipudi N. Babu

  DOI：10.1021/jo971622e

  日期：1998.4.1

  acid-catalyzed method for the synthesis of (Z)-3-butylidenephthalides 5 and a novel and general route to 3-alkyl-8-hydroxy/methoxyisocoumarins 6-8 from phthalides 9 is described. The hydroxyphthalides 4 and 10 were obtained by condensation of the phthalide anion with butyraldehyde and acetaldehyde. Reaction of hydroxyphthalides 4 with a mixture of orthophosphoric acid and formic acid gave the (Z)-3

  描述了一种新的酸催化的合成（Z）-3-丁二烯酞化物5的方法，以及从酞化物9制备3-烷基-8-羟基/甲氧基异香豆素6-8的新颖且通用的路线。通过将邻苯二甲酸酯阴离子与丁醛和乙醛缩合获得羟基邻苯二甲酸酯4和10。羟基邻苯二甲酸酯4与正磷酸和甲酸的混合物反应，得到（Z）-3-丁叉萘二甲酸酯5，而羟基邻苯二甲酸酯4和10与对甲苯磺酸反应生成3-烷基异香豆素6-8。本方法允许异香豆素中3-取代基的变化以及异香豆素和亚烷基萘的芳环上官能化的模式。
• Total Synthesis of (±)-Cephalosol via Silyl Enol Ether Acylation
  作者：Ulrich Koert、Alexander Arlt

  DOI：10.1055/s-0029-1218647

  日期：2010.3

  (±)-cephalosol is reported. Key steps are the acylation of a silyl enol ether with monomethyl oxalyl chloride and the subsequent acid-mediated ring closure to the isocoumarin structure. A chemoselective allylation and the conversion of the olefin into a methyl acetate were applied to install the γ-lactone moiety. acylation - cephalosol - chemoselectivity - isocoumarins - lactones

  报道了一种有效的全合成（±）-脑磷脂。关键步骤是将甲硅烷基烯醇醚与单甲基草酰氯酰化，然后将酸介导的闭环成异香豆素结构。应用化学选择性烯丙基化和烯烃转化为乙酸甲酯以安装γ-内酯部分。 酰化-头孢菌素-化学选择性-异香豆素-内酯

表征谱图