(-)-(6S)-6-[furan-3-yl]-5,6-dihydropyran-2-one | 212969-16-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (-)-(6S)-6-[furan-3-yl]-5,6-dihydropyran-2-one
• 英文别名: (S)-6-(furan-3-yl)-5,6-dihydro-2H-pyran-2-one；(S)-6-furan-3-yl-5,6-dihydropyran-2-one；(2S)-2-(furan-3-yl)-2,3-dihydropyran-6-one
• CAS: 212969-16-9
• 化学式: C₉H₈O₃
• 分子量: 164.161
• InChiKey: IGIDJHHPJPZISH-QMMMGPOBSA-N

物化性质

• 沸点：
  316.4±42.0 °C(Predicted)
• 密度：
  1.222±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  39.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (-)-(6S)-6-[furan-3-yl]-5,6-dihydropyran-2-one 在 正丁基锂 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 20.0h， 生成 (3S,4R,6S)-3-allyl-4-(1,1-dimethylallyl)-6-furan-3-yl-tetrahydropyran-2-one
  参考文献：
  名称：

  Enantioselective Synthesis of the Molluscicidal Furanosesquiterpene Lactones Ricciocarpin A and Ricciocarpin B via Ring Closing Metathesis

  摘要：

  Using two catalytic ring closing metatheses the key events, a short, completely diastereoselective and highly enantioselective access to the molluscicidal sesquiterpenoids ricciocarpin A and ricciocarpin B was achieved. The hitherto unknown absolute configuration of these natural products is unambiguously established.

  DOI：

  10.1002/1615-4169(200208)344:6/7<720::aid-adsc720>3.0.co;2-#
• 作为产物：
  描述：

  3-糠醛 在 sodium hydroxide 、 sodium tetrahydroborate 、 lipase from Pseudomonas fluorescens 、 二乙基甲氧基硼烷 、 三氟化硼乙醚 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 为溶剂， 反应 7.0h， 生成 (-)-(6S)-6-[furan-3-yl]-5,6-dihydropyran-2-one
  参考文献：
  名称：

  酶和化学方法对映选择性地合成Manoalide和Cacospongionolide B的吡喃呋喃酮部分

  摘要：

  报道了导致对映异构体富集形式的Manoalide和Cacospongionolide B的吡喃呋喃酮部分的两个合成序列。关键步骤涉及对映选择性羟醛缩合或酶促拆分。

  DOI：

  10.1016/s0040-4020(00)00122-8

文献信息

• Lewis Base/Brønsted Acid Co‐Catalyzed Asymmetric Thiolation of Alkenes with Acid‐Controlled Divergent Regioselectivity
  作者：Hui‐Yun Luo、Jia‐Wei Dong、Yu‐Yang Xie、Xu‐Feng Song、Deng Zhu、Tongmei Ding、Yuanyuan Liu、Zhi‐Min Chen

  DOI：10.1002/chem.201904028

  日期：2019.12.2

  A divergent strategy for the facile preparation of various enantioenriched phenylthio-substituted lactones was developed based on Lewis base/Brønsted acid co-catalyzed thiolation of homoallylic acids. The acid-controlled regiodivergent cyclization (6-endo vs. 5-exo) and acid-mediated stereoselective rearrangement of phenylthio-substituted lactones were explored. Experimental and computational studies

  基于路易斯碱/布朗斯台德酸共催化的均烯丙基酸的硫醇化反应，开发了一种简便制备各种对映体富集的苯硫基取代的内酯的策略。探索了酸控制的区域发散环化（6-endo vs. 5-exo）和苯硫基取代的内酯的酸介导的立体选择性重排。进行了实验和计算研究以阐明区域选择性和对映选择性的起源。计算结果表明，CO和CS键的形成可能会同时发生，而不会形成通常认为的催化剂配位的硫鎓离子中间体，而且底物和SPh之间的潜在π-π堆积是对映确定步骤的重要因素。最后，
• Enantioselective Synthesis of the Ricciocarpins A and B
  作者：Christoph Held、Roland Fröhlich、Peter Metz

  DOI：10.1002/1521-3773(20010316)40:6<1058::aid-anie10580>3.0.co;2-3

  日期：2001.3.16
• An easy approach to chiral non-racemic 6-(furan-3-yl)-5,6-dihydro-pyran-2-ones
  作者：Annunziata Soriente、Margherita De Rosa、Patrizia Dovinola、Guido Sodano、Arrigo Scettri

  DOI：10.1016/s0957-4166(98)00210-9

  日期：1998.7

  Chiral non-racemic 6-(furan-3-yl)-pyran-2-one derivatives, key-intermediates in the preparation of compactin, manoalide and cacospongionolide subunits, are easily accessible through a rapid and convenient six-step sequence. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Enantioselective Synthesis of Pyranofuranone Moieties of Manoalide and Cacospongionolide B by Enzymatic and Chemical Approach
  作者：Margherita De Rosa、Annunziata Soriente、Guido Sodano、Arrigo Scettri

  DOI：10.1016/s0040-4020(00)00122-8

  日期：2000.3

  Two synthetic sequences leading to the pyranofuranone moieties of Manoalide and Cacospongionolide B in enantiomerically enriched forms are reported. The key steps involve either an enantioselective aldol condensation or an enzymatic resolution.

  报道了导致对映异构体富集形式的Manoalide和Cacospongionolide B的吡喃呋喃酮部分的两个合成序列。关键步骤涉及对映选择性羟醛缩合或酶促拆分。
• Enantioselective Synthesis of the Molluscicidal Furanosesquiterpene Lactones Ricciocarpin A and Ricciocarpin B <i>via</i> Ring Closing Metathesis
  作者：Christoph Held、Roland Fröhlich、Peter Metz

  DOI：10.1002/1615-4169(200208)344:6/7<720::aid-adsc720>3.0.co;2-#

  日期：2002.8

  Using two catalytic ring closing metatheses the key events, a short, completely diastereoselective and highly enantioselective access to the molluscicidal sesquiterpenoids ricciocarpin A and ricciocarpin B was achieved. The hitherto unknown absolute configuration of these natural products is unambiguously established.