丁酸3-(乙酰氧基)-甲酯 | 89422-42-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 丁酸3-(乙酰氧基)-甲酯
• 英文名称: methyl 3-acetoxybutyrate
• 英文别名: 3-Acetoxy-buttersaeuremethylester；3-(acetyloxy)-butanoic acid, methyl ester；Methyl butanoate, 3-acetoxy；methyl 3-acetyloxybutanoate
• CAS: 89422-42-4
• 化学式: C₇H₁₂O₄
• 分子量: 160.17
• InChiKey: GSQSJDKJUCRGGT-UHFFFAOYSA-N

物化性质

• 沸点：
  92-94 °C(Press: 20 Torr)
• 密度：
  1.057±0.06 g/cm3(Predicted)
• LogP：
  0.547 (est)
• 保留指数：
  1011;1010;1016;1017

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 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：

  (+/-)-3-Acetoxy-buttersaeure 以 氯仿 为溶剂， 反应 5.0h， 生成 丁酸3-(乙酰氧基)-甲酯
  参考文献：
  名称：

  1,1′-OXALYLDIIMIDAZOLE, A NEW REAGENT FOR ACTIVATION OF CARBOXYLIC ACID

  摘要：

  羧酸及其盐通过标题试剂转变为1-酰基咪唑。这一反应被应用于脂肪酸的酯化过程。

  DOI：

  10.1246/cl.1983.1819

文献信息

• Hydrocarbonylation of Enol Esters Catalyzed by a Palladium(II) Complex
  作者：Kiyoshi Kudo、Yuji Oida、Koichi Mitsuhashi、Sadayuki Mori、Koichi Komatsu、Nobuyuki Sugita

  DOI：10.1246/bcsj.69.1337

  日期：1996.5

  The palladium(II)-catalyzed carbonylation of various enol esters in the presence of methanol under pressurized carbon monoxide was investigated. As typical results, the carbonylation of isopropenyl acetate afforded a cyclocarbonylation product, 2-methoxy-2,5,5-trimethyl-1,3-dioxolan-4-one, in 46% yield under carbon monoxide of 150 atm at 100 °C, whereas vinyl acetate selectively gave an α-hydroesterification product, methyl 2-acetoxypropionate, in 56% yield under 250 atm at 100 °C. On the contrary, the reaction of 3,3-dimethyl-1-buten-2-yl acetate gave exclusively a β-hydroesterification product, methyl 3-acetoxy-4,4-dimethylpentanoate, in 64% yield. The yields of these products show a maximum as a function of the base/palladium ratio and of the carbon monoxide pressure. The effects of the reaction variables, such as the MeOH/substrate ratio, the structure of the base, the base/Pd ratio, the CO pressure, and the reaction temperature, were examined for optimizing the process. The mechanisms for the unique cyclocarbonylation and highly regioselective hydrocarbonylation of enol esters involving hydridopalladium(II) intermediate are discussed.

  研究了在加压一氧化碳和甲醇存在下，钯(II)催化的各种烯醇酯的羰基化反应。作为典型结果，在150大气压、100°C的条件下，异丙烯基乙酸酯的羰基化反应得到了环状羰基化产物，2-甲氧基-2,5,5-三甲基-1,3-二氧杂环己烷-4-酮，产率为46%；而乙烯基乙酸酯在250大气压、100°C的条件下，选择性地得到了α-羟基酯化产物，乙酸甲酯-2-乙酰氧基丙酸酯，产率为56%。相反，3,3-二甲基-1-丁烯-2-基乙酸酯反应得到了唯一的β-羟基酯化产物，乙酸甲酯-3-乙酰氧基-4,4-二甲基戊酸酯，产率为64%。这些产物的产率作为碱/钯比的函数和一氧化碳压力的函数达到最大值。为了优化过程，考察了反应变量，如甲醇/底物比、碱的结构、碱/钯比、一氧化碳压力和反应温度等的影响。讨论了含氢钯(II)中间体参与的烯醇酯独特环羰基化和高度区域选择性羟基羰基化的机理。
• [EN] NEW COMPOUNDS, PHARMACEUTICAL COMPOSITION AND METHODS RELATING THERETO<br/>[FR] NOUVEAUX COMPOSÉS, COMPOSITION PHARMACEUTIQUE ET PROCÉDÉS CORRESPONDANTS
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2010149684A1

  公开（公告）日：2010-12-29

  New compounds are disclosed which have utility in the treatment of a variety of metabolic related conditions in a patient. The compounds of this invention have the structure (I): wherein R1, R2, R3, n, p, q, and Ar are as defined herein, including stereoisomers, solvates and pharmaceutically acceptable salts thereof. Also disclosed are pharmaceutical compositions comprising a compound of this invention, as well as methods relating to the use thereof in a patient in need thereof.

  本发明公开了具有结构(I)的新化合物，其在患者中治疗各种与代谢相关的病症具有实用性：其中R1、R2、R3、n、p、q和Ar如本文所定义，包括立体异构体、溶剂合物和药学上可接受的盐。还公开了包含本发明化合物的药物组合物，以及关于其在有需要的患者中使用的方法。
• The reaction of lead tetraacetate with alicyclic alcohols—I cycloalkanols
  作者：M.Lj. Mihailovič、Ž. Čeković、V. Andrejević、R. Matić、D. Jeremić

  DOI：10.1016/s0040-4020(01)88403-9

  日期：1968.1

  Secondary cycloalkanols, containing 4- to 16-membered rings, have been treated with lead tetraacetate in refluxing benzene. It was found that the ease of oxidation to the corresponding ketones follows the reactivity order of reactions of alicyclic compounds involving an sp3 → sp2 ring carbon hybridization change, and that the amount of β-fragmentation resulting in opening of the ring is in accord with

  含有4至16元环的仲环烷醇已在回流的苯中用四乙酸铅处理过。已发现氧化成相应酮的难易程度遵循脂环化合物涉及sp 3 → sp 2的反应的反应顺序。环碳杂化的变化，以及导致环打开的β片段的数量与与碳环相关的总应变相符。分子内醚形成的产率似乎取决于过渡态的环大小和构象因素。它从环己醇增加到环辛醇，对于环十二烷醇急剧下降，在环十六烷醇中达到最大值。在环癸醇的情况下获得的主要醚是反式-1，2-环氧环癸烷。
• Palladium(II)-Catalyzed Cyclocarbonylation of Enol Ester of Acetone. A Novel Synthesis of 1,3-Dioxolan-4-one
  作者：Kiyoshi Kudo、Koichi Mitsuhashi、Sadayuki Mori、Koichi Komatsu、Nobuyuki Sugita

  DOI：10.1246/cl.1993.1615

  日期：1993.9

  The cyclocarbonylation of isopropenyl acetate(1) to produce 2-methoxy-2,5,5-trimethyl-1,3-dioxolan-4-one(2) by use of palladium(II)-phoshine catalyst with methanol in benzene solution was studied at 100 °C under 200 atm of CO. Conversion of up to 98% and yield to 2 as high as 67% were attained.

  乙酸异丙烯酯(1)环羰基化制备2-甲氧基-2,5,5-三甲基-1,3-二氧戊环-4-酮(2),采用钯(II)-膦催化剂与甲醇在苯溶液中的反应为在 100 °C 和 200 atm CO 下进行研究。达到了高达 98% 的转化率和高达 67% 的 2 的产率。
• Cleavage of -butyldimethylsilyl ether with -butyl hydroperoxide and dioxobis(2,4-pentanedionato)molybdenum(vi) system
  作者：Takeshi Hanamoto、Takashi Hayama、Tsutomu Katsuki、Masaru Yamaguchi

  DOI：10.1016/s0040-4039(01)91365-6

  日期：1987.1

  A combination of -butyl hydroperoxide (TBHP) and MoO2(acac)2 which is a mild epoxidation system, was found to be also effective for the cleavage of -butyldimethylsilyl (TBDMS) ethers.

  的组合丁基过氧化氢（TBHP）和的MoO 2（乙酰丙酮）2，其是一个温和的系统环氧化，被认为是也有效的裂解丁基二甲基硅烷基（TBDMS）醚。

表征谱图