cis-2,5-bis(acetoxymethyl)tetrahydrofuran | 119873-51-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: cis-2,5-bis(acetoxymethyl)tetrahydrofuran
• 英文别名: (+/-)-[(2S,5R)-tetrahydrofuran-2,5-diyl]bis(methyl) diacetate；(tetrahydrofuran-2,5-diyl)bis(methylene) diacetate；[(2R,5S)-5-(acetyloxymethyl)oxolan-2-yl]methyl acetate
• CAS: 119873-51-7
• 化学式: C₁₀H₁₆O₅
• 分子量: 216.234
• InChiKey: PXKOWWAMUSQKRL-AOOOYVTPSA-N

物化性质

• 沸点：
  105.5-106.5 °C(Press: 0.5 Torr)
• 密度：
  1.109±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  cis-2,5-bis(acetoxymethyl)tetrahydrofuran 在 pig liver esterase chromium(VI) oxide 、 phosphate buffer 作用下， 以 水 为溶剂， 反应 18.0h， 生成 (2S,5R)-5-Acetoxymethyl-tetrahydro-furan-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Enzyme-catalyzed Asymmetric Hydrolysis ofmeso-Substrate. The Facile Synthesis of Both Enantiomers ofcis-2,5-Disubstituted Tetrahydrofuran Derivatives

  摘要：

  在PLE、PPL和CCL存在的情况下，由顺式-2,5-双(羟甲基)四氢呋喃衍生的中位二酯通过酶催化不对称水解，得到具有光学活性的半酯。从半酯中制备出具有高光学纯度的顺式-5-(羟甲基)四氢呋喃-2-羧酸的两种对映异构体。

  DOI：

  10.1246/cl.1988.1717
• 作为产物：
  描述：

  2,5-呋喃二甲醇 在 吡啶 、 Raney Ni (W-5) 、 氢气 作用下， 以 乙醇 为溶剂， 25.0~100.0 ℃ 、12.16 MPa 条件下， 反应 24.0h， 生成 cis-2,5-bis(acetoxymethyl)tetrahydrofuran
  参考文献：
  名称：

  Enzyme-catalyzed asymmetric acylation and hydrolysis of cis-2,5-disubstituted tetrahydrofuran derivatives: Contribution to development of models for reactions catalyzed by porcine liver esterase and porcine pancreatic lipase

  摘要：

  Pig liver esterase, lipase from porcine pancreas, lipase from Pseudomonas sp. (lipase YS), and lipase from Candida cylindracea catalyzed hydrolyses of the cis-diacetate 1 and the trans-diacetate (+/-)-4 to give the cis-monoacetate 3 and the trans-monoacetate 6 in optically active forms, respectively. Lipase YS-catalyzed acylations of the cis-diol 2 and the trans-diol (+/-)-5 with an acylating agent in cyclohexane yielded (-)-3 and (-)-6, respectively. The group adjacent to the R stereogenic center preferentially reacted in lipase YS-catalyzed hydrolyses of 1 and (+/-)-4 and acylations of 2 and (+/-)-5, and the enantioselectivities are rationalized by our rule recently proposed for lipase YS.

  DOI：

  10.1016/s0957-4166(00)80131-7

文献信息

• A General Synthesis of Bis-α-acyloxy-1,4- and -1,5-diketones Through Catalytic Oxidative Opening of Acylated THF and THP Diols
  作者：Vincenzo Piccialli、Stefano D'Errico、Nicola Borbone、Giorgia Oliviero、Roberto Centore、Sabrina Zaccaria

  DOI：10.1002/ejoc.201201554

  日期：2013.3

  The first general synthesis of bis-α-acyloxy-1,4- and -1,5-diketones has been accomplished in a catalytic oxidative opening of bis-acylated THF and THP (tetrahydropyran) diols, which were synthesised by osmium- or ruthenium-catalysed oxidative cyclisation of 1,5- and 1,6-dienes. The overall sequence corresponds to the regioselective double ketoacyloxylation of the starting diene. The synthesised bis-α-acyloxy-1

  双-α-酰氧基-1,4-和-1,5-二酮的首次一般合成是在双酰化的 THF 和 THP（四氢吡喃）二醇的催化氧化开环中完成的，这些二醇是由锇或钌合成的-催化氧化环化 1,5- 和 1,6- 二烯。整个序列对应于起始二烯的区域选择性双酮酰氧基化。合成的双-α-酰氧基-1,5-二羰基化合物已转化为基于吡啶的氧化钳配体或吡嗪二甲醇物质，从而发现了前所未有的芳构化路线。
• Lipophilic Oligopeptides for Chemo- and Enantioselective Acyl Transfer Reactions onto Alcohols
  作者：Christian E. Müller、Daniela Zell、Radim Hrdina、Raffael C. Wende、Lukas Wanka、Sören M. M. Schuler、Peter R. Schreiner

  DOI：10.1021/jo401195c

  日期：2013.9.6

  Inspired by the extraordinary selectivities of acylases, we envisioned the use of lipophilic oligopeptidic organocatalysts for the acylative kinetic resolution/desymmetrization of rac- and meso-cycloalkane-1,2-diols. Here we describe in a full account the discovery and development process from the theoretical concept to the final catalyst, including scope and limitations. Competition experiments with various alcohols and electrophiles show the full potential of the employed oligopeptides. Additionally, we utilized NMR and IR-spectroscopic methods as well as computations to shed light on the factors responsible for the selectivity. The catalyst system can be readily modified to a multicatalyst by adding other catalytically active amino acids to the peptide backbone, enabling the stereoselective one-pot synthesis of complex molecules from simple starting materials.
• NAEMURA, KOICHIRO;TAKAHASHI, NOBUO;CHIKAMATSU, HIROAKI, CHEM. LETT.,(1988) N 10, C. 1717-1720
  作者：NAEMURA, KOICHIRO、TAKAHASHI, NOBUO、CHIKAMATSU, HIROAKI

  DOI：——

  日期：——