(3-氧代-1H-2-苯并呋喃-1-基)丁酸酯 | 108761-29-1

• 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-氧代-1H-2-苯并呋喃-1-基)丁酸酯
• 英文名称: 3-oxo-1,3-dihydro-1-isobenzofuranyl butyrate
• 英文别名: 3-(butanoyloxy)phthalide；(±)-3-phthalideyl butyrate；(3-Butyroxy)phthalide；3-(butyroyloxy)phthalide；Butanoic acid, 1,3-dihydro-3-oxo-1-isobenzofuranyl ester；(3-oxo-1H-2-benzofuran-1-yl) butanoate
• CAS: 108761-29-1
• 化学式: C₁₂H₁₂O₄
• 分子量: 220.225
• InChiKey: LZBZVXBQAJUKGA-UHFFFAOYSA-N

物化性质

• 沸点：
  353.1±42.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  丁酸酐 、 3-羟基异苯并呋喃-1(3H)-酮 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以83%的产率得到(3-氧代-1H-2-苯并呋喃-1-基)丁酸酯
  参考文献：
  名称：

  由2-甲酰基苯甲酸合成富含对映体的邻苯二甲酸酯和异吲哚啉酮衍生物

  摘要：

  这份手稿是专门为迪特·恩德斯教授在他的70之际个生日，他为有机化学开创性的贡献。 抽象的 2-甲酰基苯甲酸的转化提供了直接进入一系列杂环有机化合物的途径，例如邻苯二甲酸盐和异吲哚啉酮。在这里，我们使用（+）-辛可宁作为催化剂，结合九氟叔丁醇作为氢键供体，通过动态动力学拆分提供对映体富集的酰化3-羟基邻苯二酚，收率高达99％，ee高达90％。此外，由2-甲酰基苯甲酸合成了各种3-烷氧基邻苯二甲酸酯以及2-烷基-3-羟基-1-异吲哚啉酮。 2-甲酰基苯甲酸的转化提供了直接进入一系列杂环有机化合物的途径，例如邻苯二甲酸盐和异吲哚啉酮。在这里，我们使用（+）-辛可宁作为催化剂，结合九氟叔丁醇作为氢键供体，通过动态动力学拆分提供对映体富集的酰化3-羟基邻苯二酚，收率高达99％，ee高达90％。此外，由2-甲酰基苯甲酸合成了各种3-烷氧基邻苯二甲酸酯以及2-烷基-3-羟基-1-异吲哚啉酮。

  DOI：

  10.1055/s-0036-1589404

文献信息

• Palladium-catalyzed synthesis of 3-oxo-1,3-dihydro-1-isobenzofuranyl alkanoates from 2-bromobenzaldehyde and sodium alkanoates
  作者：Chan Sik Cho、Dong Yeol Baek、Sang Chul Shim

  DOI：10.1002/jhet.5570360145

  日期：1999.1

  2-Bromobenzaldehyde reacts with sodium alkanoates in acetonitrile under carbon monoxide pressure in the presence of a catalytic amount of bis(triphenylphosphine)palladium(II) chloride to afford the corre sponding 3-oxo-1,3-dihydro-1-isobenzofuranyl alkanoates in moderate to good yields.

  2-溴苯甲醛在催化量的双（三苯基膦）钯（II）存在下于一氧化碳压力下与链烷酸钠在乙腈中反应，得到相应的3-氧代-1,3-二氢-1-异苯并呋喃基烷酸酯中等至良好的产量。
• Facile Palladium-Catalyzed Synthesis of 3-oxo- 1,3-Dihydro-1-Isobenzofuranyl Alkanoates From 2-Bromobenzaldehyde and Carboxylic Acids
  作者：Chan Sik Cho、Dong Yeol Baek、Hye-Young Kim、Sang Chul Shim、Dae Hee Oh

  DOI：10.1080/00397910008087130

  日期：2000.3

  Abstract 2-Bromobenzaldehyde reacts with carboxylic acids in acetonitrile under carbon monoxide pressure in the presence of a catalytic amount of a palladium catalyst to give the corresponding 3-oxo-1,3-dihydro-1-isobenzofuranyl alkanoates in high yields.

  摘要 2-溴苯甲醛在一氧化碳压力下，在一氧化碳压力下，在催化量的钯催化剂存在下与羧酸反应，以高产率得到相应的3-氧代-1,3-二氢-1-异苯并呋喃基链烷酸酯。
• Biologically active carboxylic acid esters
  申请人：Kupat Holim Health Insurance Institution of the General Federation of

  公开号：US05200553A1

  公开（公告）日：1993-04-06

  Biologically active carboxylic acid esters which promote antitumor or immune response are selected from the group consisting of compounds having formulas (I), (II) and (III): XCH.sub.2 --CHX--CHX--C(.dbd.O)--O--Z (I) CH.sub.3 --CO--CH.sub.2 --C(.dbd.O)--O--Z (II) CH.sub.3 --CH.sub.2 --CO--C(.dbd.O)--O--Z (III) wherein X is H, or one X only may be OH; Z is --CHR--O--(O.dbd.)C--R', R represents a member selected from the group consisting of hydrogen and alkyl, and R' represents a member of the group consisting of alkyl, aminoalkyl, aralkyl, aryl, alkoxy, aralkoxy and aryloxy, in which aryl by itself, and aryl in aralkyl, aralkoxy and aryloxy, are each selected from the group consisting of sub-groups (a) and (b), wherein (a) is unsubstituted phenyl, napthyl, furyl or thienyl, and (b) is phenyl, napthyl, furyl or thienyl, each of which is substituted by at least one substituent selected from the group consisting of alkyl, alkoxy or halogen, provided that in (I) when X is H and R' is propyl, then R is alkyl which contains at least three carbon atoms.

  从具有以下化学式的化合物中选择促进抗肿瘤或免疫反应的生物活性羧酸酯：XCH.sub.2 --CHX--CHX--C(.dbd.O)--O--Z (I) CH.sub.3 --CO--CH.sub.2 --C(.dbd.O)--O--Z (II) CH.sub.3 --CH.sub.2 --CO--C(.dbd.O)--O--Z (III) 其中X为H，或仅有一个X可能为OH；Z为--CHR--O--(O.dbd.)C--R'，R代表从氢和烷基中选择的成员，R'代表从烷基、氨基烷基、芳基烷基、芳基、烷氧基、芳基烷氧基和芳基氧基中选择的成员，其中芳基本身，以及芳基在芳基烷基、芳基烷氧基和芳基氧基中，每个都从亚组（a）和（b）中选择，其中（a）是未取代的苯基、萘基、呋喃基或噻吩基，（b）是苯基、萘基、呋喃基或噻吩基，每个都至少被来自烷基、烷氧基或卤素的一种取代基取代，但在（I）中，当X为H且R'为丙基时，则R为含有至少三个碳原子的烷基。
• Process for preparation of aromatic polycarboxylic acids and intermediates therefor
  申请人：THE UPJOHN COMPANY

  公开号：EP0125342A1

  公开（公告）日：1984-11-21

  A method is described for autoxidizing particular ortho-dialkyl substituted aromatic compounds using a particular type of solvent which gives rise to the formation of 3-alkanoyloxyphthalide compounds, some of which are novel. The phthalides in turn are ionically oxidized to their corresponding aromatic polycarboxylic acids. Combination of the two methods provides a means for converting ortho dialkyl substituted aromatic compounds directly to the corresponding polycarboxylic acids in higher yields and at generally lower overall temperatures and reaction conditions compared to prior art methods. Polycarboxylic acids so obtained are known to be useful in the preparation of alkyds, polyesters, and the like, and, particularly, in the formation of the corresponding acid anhydrides which are used in the preparation of organic high temperature polymers such as polyamides, polyamideimides, and polyimides.

  描述了一种使用特定类型溶剂对特定邻二烷基取代的芳香族化合物进行自氧化的方法，该方法可生成 3-烷酰氧基邻苯二甲酸盐化合物，其中一些是新型化合物。 这些邻苯二甲酸盐又被离子氧化成相应的芳香族多羧酸。 与现有技术相比，这两种方法的结合提供了一种将正交二烷基取代的芳香族化合物直接转化为相应的聚羧酸的方法，收率更高，总体温度和反应条件通常更低。 众所周知，这样得到的聚羧酸可用于制备醇酸树脂、聚酯等，特别是形成相应的酸酐，用于制备有机高温聚合物，如聚酰胺、聚酰胺酰亚胺和聚酰亚胺。
• Novel anticancer prodrugs of butyric acid. 2
  作者：Abraham Nudelman、Margaretta Ruse、Adina Aviram、Ester Rabizadeh、Matityahu Shaklai、Yael Zimrah、Ada Rephaeli

  DOI：10.1021/jm00082a009

  日期：1992.2

  The antitumor activity of novel prodrugs butyric acid was examined. The in vitro effect of the compounds on induction of cytodifferentiation and on inhibition of proliferation and clonogenicity showed that (pivaloyloxy)methyl butyrate (1a) (labeled AN-9) was the most active agent. SAR's suggested that its activity stemmed from hydrolytically released butyric acid. In vivo, 1a displayed antitumor activity in B16F0 melanoma primary cancer model, manifested by a significant increase in the life span of the treated animals. Murine lung tumor burden, induced by injection of the highly metastatic melanoma cells (B16F10.9), was decreased by 1a. It also displayed a significant therapeutic activity against spontaneous metastases which were induced by 3LL Lewis lung carcinoma cells. Moreover, 1a has the advantage of low toxicity, with an acute LD50 = 1.36 +/- 0.1 g/kg (n = 5). These results suggest that 1a is a potential antineoplastic agent.