3-羟基-6-甲基-2-苯并呋喃-1(3H)-酮 | 177166-16-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 中文名称: 3-羟基-6-甲基-2-苯并呋喃-1(3H)-酮
• 英文名称: 3-Hydroxy-6-methylphthalid
• 英文别名: 3-hydroxy-6-methylisobenzofuran-1(3H)-one；3-hydroxy-6-methyl-3H-2-benzofuran-1-one
• CAS: 177166-16-4
• 化学式: C₉H₈O₃
• 分子量: 164.161
• InChiKey: MMBMVWIMZJFMIR-UHFFFAOYSA-N

物化性质

• 熔点：
  223-224 °C
• 沸点：
  387.9±42.0 °C(Predicted)
• 密度：
  1.375±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-羟基-6-甲基-2-苯并呋喃-1(3H)-酮 生成 2-Formyl-5-methyl-benzoesaeuremethylester
  参考文献：
  名称：

  TSUDZI, MASAXIRO;KOYAMA, XIROYASU;SUDZUKI, JOSIKUNI

  摘要：

  DOI：
• 作为产物：
  描述：

  2,5-二甲基苯甲酸甲酯 在 palladium on activated charcoal calcium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 过氧化氢苯甲酰 、 水 、 氢气 作用下， 以 1,4-二氧六环 、 四氯化碳 为溶剂， 180.0 ℃ 、275.79 kPa 条件下， 反应 55.0h， 生成 3-羟基-6-甲基-2-苯并呋喃-1(3H)-酮
  参考文献：
  名称：

  Aromatische Spirane, 21. Mitt: Darstellung von Methylphthalaldehyds�uren und ihren Ethylund Methylestern als Synthone f�r Synthesen von methylierten 2,2?-Spirobiindandionen

  摘要：

  The isomeric methyl phthalaldehydic acids 11 were obtained from phthalides 4 by bromation (NBS) to the 3-bromo derivatives 7 and subsequent hydrolysis with water. 4 in turn were accessible from dimethyl methyl benzoates 1 by dibromination with NBS and subsequent thermical cyclization to the bromo derivatives 3 which, on catalytic dehalogenation, afforded the phthalides 4. Reaction of 11 with methanol or ethanol gave the pseudo-esters 13 and 14, resp. Short treatment of 11 with diazomethane on the other hand yielded the methyl formyl benzoates 15b to 15e. Prolonged reaction (several hours) gave the oxiranyl compounds 17; in addition, the acetonyl derivatives 18 were also found, obviously formed by a double methylene insertion into 15. All reactions proceeded with good to excellent yields.

  DOI：

  10.1007/bf00807401

文献信息

• Chiral Bicyclic Imidazole‐Catalyzed Acylative Dynamic Kinetic Resolution for the Synthesis of Chiral Phthalidyl Esters
  作者：Muxing Zhou、Tatiana Gridneva、Zhenfeng Zhang、Ende He、Yangang Liu、Wanbin Zhang

  DOI：10.1002/anie.202012445

  日期：2021.1.18

  Utilizing a chiral bicyclic imidazole organocatalyst and adopting a continuous injection process, an alternative route has been developed for the efficient synthesis of chiral phthalidyl ester prodrugs via dynamic kinetic resolution of 3‐hydroxyphthalides through enantioselective acylation (up to 99 % ee). The computational studies suggest a general base catalytic mechanism differing from the widely

  利用手性双环咪唑有机催化剂并采用连续注射工艺，已开发出另一种途径，可通过对映选择性酰化作用（3-99％ee）动态动力学拆分3-羟基邻苯二酚来有效合成手性邻苯二甲酸酯基前药。计算研究表明，一般的基础催化机理不同于广泛接受的亲核催化机理。关键过渡态的结构分析表明，催化剂与底物之间的CH-π相互作用而不是先前考虑的阳离子/π-π相互作用是引起观察到的立体控制的主要因素。
• DERIVATIVES OF UNCIALAMYCIN, METHODS OF SYNTHESIS AND THEIR USE AS ANTITUMOR AGENTS
  申请人：WILLIAM MARSH RICE UNIVERSITY

  公开号：US20160185791A1

  公开（公告）日：2016-06-30

  In one aspect, the present disclosure provides new analogs of uncialamycin of formulae (I) and (II). The present disclosure also provides novel synthetic pathways to obtaining uncialamycin and analogs thereof. Additionally, the present disclosure also describes methods of use of uncialamycin and analogs thereof. In another aspect, the present disclosure provides antibody-drug conjugates comprising the compounds of formulae (I) and (II).

  在某个方面，本公开提供了式（I）和（II）的新的uncialamycin类似物。本公开还提供了获得uncialamycin及其类似物的新型合成途径。此外，本公开还描述了uncialamycin及其类似物的使用方法。在另一方面，本公开提供了包含式（I）和（II）化合物的抗体药物偶联物。
• Regioselective Pd-Catalyzed Aerobic Aza-Wacker Cyclization for Preparation of Isoindolinones and Isoquinolin-1(2<i>H</i>)-ones
  作者：Guoqiang Yang、Wanbin Zhang

  DOI：10.1021/ol203043h

  日期：2012.1.6

  A switchable regioselective intramolecular aerobic aza-Wacker cyclization catalyzed by palladium is presented. Isolndollnones or isoquinolin1(2H)-ones could be prepared selectively from the same substrates using different catalysts. The type and steric hindrance of the ligands may be the variables most significant for regiocontrol.
• TSUDZI, MASAXIRO;KOYAMA, XIROYASU;SUDZUKI, JOSIKUNI
  作者：TSUDZI, MASAXIRO、KOYAMA, XIROYASU、SUDZUKI, JOSIKUNI

  DOI：——

  日期：——
• SPIRO-TETRACYCLIC RING COMPOUNDS AS BETASECRETASE MODULATORS AND METHODS OF USE
  申请人：Amgen Inc.

  公开号：EP2328903B1

  公开（公告）日：2014-03-05