(+/-)-2-acetoxymethyl-2,3-dihydrobenzofuran | 91142-88-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 香豆素
• 英文名称: (+/-)-2-acetoxymethyl-2,3-dihydrobenzofuran
• 英文别名: 2-(acetoxymethyl)-2,3-dihydrobenzofuran；acetic acid-(2,3-dihydro-benzofuran-2-ylmethyl ester)；Essigsaeure-(2,3-dihydro-benzofuran-2-ylmethylester)；2-Acetoxymethyl-cumaran；3-Acetoxymethylcoumaran；2,3-Dihydro-1-benzofuran-2-ylmethyl acetate
• CAS: 91142-88-0
• 化学式: C₁₁H₁₂O₃
• 分子量: 192.214
• InChiKey: YHCHYWNREUWZHR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-烯丙基酚 在 吡啶 、 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 反应 12.0h， 生成 (+/-)-2-acetoxymethyl-2,3-dihydrobenzofuran
  参考文献：
  名称：

  Enantioselective acylation of 2-hydroxymethyl-2,3-dihydrobenzofurans catalysed by lipase from Pseudomonas cepacia (Amano PS) and total stereoselective synthesis of (−)-(R)-MEM-protected arthrographol

  摘要：

  Lipase Amano PS catalysed acylation of (+/-)-2-hydroxymethyl-2,3-dihydrobenzofurans using vinyl acetate as the acyl donor in n-hexane gave (-)-(R)-2-acetoxymethyl-2,3-dihydrobenzo and (+)-(S)-2-hydroxymethyl-2,3-dihydrobenzofurans in high enantiomeric excess. (-)-(R)-Acetate 18j is converted to (-)-(R)-MEM-protected arthrographol 22. (C) 2000 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(00)00302-5

文献信息

• C- ARYL GLYCOSID DERIVATIVES, PHARMACEUTICAL COMPOSITION, PREPARATION PROCESS AND USES THEREOF
  申请人：SHANGHAI DE NOVO PHARMATECH CO. LTD.

  公开号：US20170037038A1

  公开（公告）日：2017-02-09

  This invention relates to a kind of C-aryl glycoside derivatives, its pharmaceutical compositions, preparation methods, and uses thereof. The preparation method comprises: method 1: in a solvent, deprotecting the acetyl protecting groups of compound 1-f in the presence of a base; method 2: 1) compound 2-g reacts with via Mitsunobu reaction; 2) deprotecting the acetyl protecting groups of compound 2-f obtained from step 1; method 3: 1) compound 2-g reacts with via nucleophilic substitution reaction; 2) deprotecting the acetyl protecting groups of compound 3-f obtained from step 1. The pharmaceutical composition comprises a kind of C-aryl glycoside derivatives; it's pharmaceutically acceptable salts and/or prodrugs thereof and excipient thereof. This invention further relates to a kind of C-aryl glycoside derivatives, it's pharmaceutically acceptable salts or pharmaceutical compositions thereof for the use in preparation of a SGLT inhibitor. The C-aryl glycoside derivatives of this invention provides a new direction for the study of SGLT inhibitors.

  这项发明涉及一种C-芳基糖苷衍生物，其药物组合物、制备方法及其用途。制备方法包括：方法1：在溶剂中，在碱的存在下去保护化合物1-f的乙酰保护基；方法2：1）化合物2-g通过Mitsunobu反应发生反应；2）去除从步骤1得到的化合物2-f的乙酰保护基；方法3：1）化合物2-g通过亲核取代反应发生反应；2）去除从步骤1得到的化合物3-f的乙酰保护基。药物组合物包括一种C-芳基糖苷衍生物；其药学上可接受的盐和/或前药以及赋形剂。这项发明还涉及一种C-芳基糖苷衍生物，其药学上可接受的盐或其药物组合物，用于制备SGLT抑制剂。这项发明的C-芳基糖苷衍生物为SGLT抑制剂的研究提供了新的方向。
• C-ARYL INDICAN DERIVATIVE, AND PHARMACEUTICAL COMPOSITION THEREOF, PREPARATION METHOD THEREFOR AND USES THEREOF
  申请人：Shanghai De Novo Pharmatech Co Ltd.

  公开号：EP3133071A1

  公开（公告）日：2017-02-22

  This invention relates to a kind of C- aryl glycoside derivatives, its pharmaceutical compositions, preparation methods, and uses thereof. The preparation method comprises: method 1: in a solvent, deprotecting the acetyl protecting groups of compound 1-f in the presence of a base; method 2: 1) compound 2-g reacts with via Mitsunobu reaction; 2) deprotecting the acetyl protecting groups of compound 2-f obtained from step 1; method 3: 1) compound 2-g reacts with via nucleophilic substitution reaction; 2) deprotecting the acetyl protecting groups of compound 3-f obtained from step 1. The pharmaceutical composition comprises a kind of C- aryl glycoside derivatives; it's pharmaceutically acceptable salts and/or prodrugs thereof and excipient thereof. This invention further relates to a kind of C- aryl glycoside derivatives, it's pharmaceutically acceptable salts or pharmaceutical compositions thereof for the use in preparation of a SGLT inhibitor. The C- aryl glycoside derivatives of this invention provides a new direction for the study of SGLT inhibitors.

  本发明涉及一种C-芳基苷衍生物及其药物组合物、制备方法和用途。其制备方法包括：方法 1：在溶剂中，在碱存在下，对化合物 1-f 的乙酰基保护基进行脱保护；方法 2：1）化合物 2-g 与碱反应；2）化合物 2-g 与碱反应；3）化合物 2-g 与碱反应；4）化合物 2-g 与碱反应；5）化合物 2-g 与碱反应；6）化合物 2-g 与碱反应。 通过 Mitsunobu 反应；2）对步骤 1 中得到的化合物 2-f 的乙酰基保护基团进行脱保护；方法 3：1）化合物 2-g 与碱反应；2）化合物 2-g 与碱反应；3）化合物 2-g 与碱反应；4）化合物 2-g 与碱反应；5）化合物 2-g 与碱反应。 通过亲核取代反应；2）对步骤 1 得到的化合物 3-f 的乙酰基保护基团进行脱保护。药物组合物包括一种 C-芳基苷衍生物；其药学上可接受的盐和/或原药及其赋形剂。本发明进一步涉及一种用于制备 SGLT 抑制剂的 C-芳基糖苷衍生物、其药学上可接受的盐或药物组合物。本发明的 C-芳基糖苷衍生物为 SGLT 抑制剂的研究提供了一个新的方向。
• Acetoxy lactonization of alkenyl acetic acids promoted by ammonium persulfate and trifluoromethanesulfonic acid in acetic acid
  作者：Marcello Tiecco、Lorenzo Testaferri、Marco Tingoli

  DOI：10.1016/s0040-4020(01)82384-x

  日期：1993.6

  The reactions of substituted 4-pentenoic and 3-butenoic acids with ammonium persulfate in acetic acid, in the presence of trifluoromethanesulfonic acid, gave the products of acetoxy lactonization in good yield.
• Pansewitsch-Koljada; Idel'tschik, Zhurnal Obshchei Khimii, 1954, vol. 24, p. 807,810; engl. Ausg. S. 809, 811
  作者：Pansewitsch-Koljada、Idel'tschik

  DOI：——

  日期：——
• Reaction of o-Alkenylphenols with Peracetic Acid
  作者：S. W. TINSLEY

  DOI：10.1021/jo01091a007

  日期：1959.9