(+)-(2S,3R)-cis-endo-3-(hydroxymethyl)bicyclo<2.2.1>hept-5-ene-2-carboxylic acid lactone | 95340-92-4

• 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: (+)-(2S,3R)-cis-endo-3-(hydroxymethyl)bicyclo<2.2.1>hept-5-ene-2-carboxylic acid lactone
• 英文别名: (2S,3R)-exo-3-oxabicyclo[2.2.1]dec-7-en-2-one；(+)-(2S,3R)-cis-endo-3-(hydroxymethyl)bicyclo[2.2.1]hept-5-ene-2-carboxylic acid lactone；(1S,2S,6R,7R)-4-oxatricyclo[5.2.1.02,6]dec-8-en-3-one
• CAS: 95340-92-4
• 化学式: C₉H₁₀O₂
• 分子量: 150.177
• InChiKey: WOJWXGGCIZZKFQ-OSMVPFSASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (1R,2R,6S,7S)-4-oxa-tricyclo[5.2.1.0^2,6]dec-8-ene-3,5-dione 在 HLADH lithium aluminium tetrahydride 、 nicotinamide adenine dinucleotide 、 2,6-蒽二酚 作用下， 反应 144.0h， 生成 (+)-(2S,3R)-cis-endo-3-(hydroxymethyl)bicyclo<2.2.1>hept-5-ene-2-carboxylic acid lactone
  参考文献：
  名称：

  Enzymes in organic synthesis. 34. Preparations of enantiomerically pure exo- and endo-bridged bicyclic [2.2.1] and [2.2.2] chiral lactones via stereospecific horse liver alcohol dehydrogenase catalyzed oxidations of meso diols

  摘要：

  DOI：

  10.1021/ja00294a052

文献信息

• Broad-Spectrum Enantioselective Diels−Alder Catalysis by Chiral, Cationic Oxazaborolidines
  作者：Do Hyun Ryu、Thomas W. Lee、E. J. Corey

  DOI：10.1021/ja027468h

  日期：2002.8.1

  catalysts for Diels-Alder addition of cyclopentadiene to a wide variety of dienophiles. Adducts have been obtained in excellent yield and enantioselectivity from alpha,beta-unsaturated esters, lactones, and cyclic ketones. The absolute facial selectivity for each of these substrates follows a common pattern which differs from that observed with alpha,beta-enals. The different reaction channels can be

  阳离子手性路易斯酸 1 和 2 由相应的中性恶唑硼烷的三氟甲磺酸质子化产生，可作为环戊二烯与各种亲二烯体的 Diels-Alder 加成反应的优良催化剂。已从 α、β-不饱和酯、内酯和环酮以优异的产率和对映选择性获得加合物。这些基质中每一种的绝对面部选择性遵循一个共同的模式，该模式不同于用 alpha,beta-enals 观察到的模式。可以根据通过复合物 3（对于 α、β-烯醛）和 4（对于 α、β-烯酮和酯）的途径来理解不同的反应通道。
• Microbial alcohol dehydrogenase screening for enantiopure lactone synthesis: Down-stream process from microtiter plate to bench bioreactor
  作者：F. Boratyński、J. Pannek、P. Walczak、A. Janik-Polanowicz、E. Huszcza、E. Szczepańska、E. Martinez-Rojas、T. Olejniczak

  DOI：10.1016/j.procbio.2014.06.019

  日期：2014.10

  One-pot conversion with whole cells of bacteria was performed for biooxidation of meso monocyclic (3a-b) and bicyclic diols (3c-e) into corresponding chiral lactones of bicyclo[4.3.0]nonane structure (2a-b) as well as exo- and endo-bridged lactones with the structure of [2.2.1] (3c-d) and [2.2.2] (3e). Micrococcus sp. DSM 30771 was selected as biocatalyst with significant alcohol dehydrogenase activity. Among tested strains, microbial oxidation of meso diols 3a-e catalyzed by Micrococcus sp. afforded enantiomerically pure ((+)-(2S,3R)-2c (ee = 99%), (+)-(2S,3R)-2e (ee = 99%)) or enriched ((+)-(1S,5R)-2a (ee = 90%), (-)-(1S,5R)-2b (ee = 86%), (+)-(2S,3R)-2d (ee = 80%)) lactone moieties. Comparative study with respect to microbial cultivation as well as biooxidation was undertaken to verify agreement of secondary metabolite biosynthesis in different scales: from MTP (4 mL), across shake flask (100 mL) till bioreactor (4 L). The results from biotransformations showed quite similar dependence in oxidation of all substrates 3a-e in MTP and flasks as well, thereby confirmed the validity and reasonable approach of using MTP for preliminary studies. (C) 2014 Elsevier Ltd. All rights reserved.