(S)-2-acetoxy-3,3-dimethyl-γ-butyrolactone | 28387-34-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (S)-2-acetoxy-3,3-dimethyl-γ-butyrolactone
• 英文别名: (S)-pantolactone acetate；2(3H)-Furanone, 3-(acetyloxy)dihydro-4,4-dimethyl-, (S)-；[(3S)-4,4-dimethyl-2-oxooxolan-3-yl] acetate
• CAS: 28387-34-0
• 化学式: C₈H₁₂O₄
• 分子量: 172.181
• InChiKey: SREJAFLAMHECEQ-ZCFIWIBFSA-N

物化性质

• 沸点：
  263.9±33.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-2-acetoxy-3,3-dimethyl-γ-butyrolactone 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 生成 (S)-(+)-泛解酸内酯
  参考文献：
  名称：

  氯甲烷磺酸盐与乙酸铯反应转化仲醇的有效方法

  摘要：

  已经进行了使用（氯甲基磺酰基）氧基作为有利的离去基团在18-冠-6存在下用乙酸铯转化各种仲醇的方法，从而以高收率得到了转化的乙酸酯。

  DOI：

  10.1016/0040-4039(96)01333-0
• 作为产物：
  描述：

  cesium acetate 、 (R)-4,4-dimethyl-2-oxotetrahydrofuran-3-yl trifluoromethanesulfonate 在 18-冠醚-6 作用下， 以 苯 为溶剂， 反应 1.5h， 以91%的产率得到(S)-2-acetoxy-3,3-dimethyl-γ-butyrolactone
  参考文献：
  名称：

  氯甲烷磺酸盐与乙酸铯反应转化仲醇的有效方法

  摘要：

  已经进行了使用（氯甲基磺酰基）氧基作为有利的离去基团在18-冠-6存在下用乙酸铯转化各种仲醇的方法，从而以高收率得到了转化的乙酸酯。

  DOI：

  10.1016/0040-4039(96)01333-0

文献信息

• HIV protease inhibiting compounds
  申请人：Randolph T. John

  公开号：US20050159469A1

  公开（公告）日：2005-07-21

  A compound of the formula is disclosed as an HIV protease inhibitor. Methods and compositions for inhibiting an HIV infection are also disclosed.

  公开了一种公式的化合物作为HIV蛋白酶抑制剂。还公开了用于抑制HIV感染的方法和组合物。
• Rapid screening of hydrolases for the enantioselective conversion of ‘difficult-to-resolve’ substrates
  作者：Markus Baumann、Bernhard H Hauer、Uwe T Bornscheuer

  DOI：10.1016/s0957-4166(00)00465-1

  日期：2000.12

  Hydrolases showing high enantio selectivity towards three racemic alcohols ( 1-methoxy-2-propanol, 3-hydroxy-tetrahydrofuran, 3-butyn-2-ol) and pantolactone were identified by a step-wise screening procedure. Initially, those biocatalysts, which exhibited hydrolytic activity towards the corresponding acetates or butyrates, were selected out of >100 enzymes. Here, rapid screening was performed in a pH-indicator-based format in microtiter plates. Subsequently, enantioselectivity of active hydrolases was determined in small scale reactions (similar to1 mg substrate per reaction) by means of gas chromatography using chiral columns. Enzymes exhibiting highest enantioselectivities were then chosen for preparative scale resolution. Using this strategy, at least one suitable hydrolase was found for 3 out of the 4 model compounds examined, allowing efficient kinetic resolution. Moreover, in all cases enantiocomplementary enzymes were identified thus enabling access to both enantiomers of all substrates. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Enzymatic kinetic resolution of pantolactone:relevance to chiral auxiliary chemistry
  作者：Louise Haughton、Jonathan M.J Williams、Jochen A Zimmermann

  DOI：10.1016/s0957-4166(00)00130-0

  日期：2000.5

  Racemic pantolactone was converted into either enantiomerically enriched pantolactone acetate or pantolactone acrylate by an enzyme-catalysed kinetic resolution process. Pantolactone is known to be a good auxiliary for acrylate ill the Diels-Alder reaction. (C) 2000 Elsevier Science Ltd. All rights reserved.
• BEVINAKATTI, H. S.;BANERJI, A. A.;NEWADKAR, R. V., J. ORG. CHEM., 54,(1989) N0, C. 2453-2455
  作者：BEVINAKATTI, H. S.、BANERJI, A. A.、NEWADKAR, R. V.

  DOI：——

  日期：——
• COREY, E. J.;HUANG, HORNG-CHIH, TETRAHEDRON LETT., 30,(1989) N9, C. 5235-5238
  作者：COREY, E. J.、HUANG, HORNG-CHIH

  DOI：——

  日期：——