(+/-)-(1S*,2R*,6S*,7R*)-2-Methyl-4-oxatricyclo<5.2.1.0^2,6>dec-8-en-3-one | 67390-36-7

• 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: (+/-)-(1S*,2R*,6S*,7R*)-2-Methyl-4-oxatricyclo<5.2.1.0^2,6>dec-8-en-3-one
• 英文别名: (3aRS,4SR,7RS,7aSR)-7a-methyl-3a,4,7,7a-tetrahydro-4,7-methanoisobenzofuran-1(3H)-one；exo-2-methylnorborn-5-ene-endo-(3-methyl-2-carbo-3a) lactone；(1S,2R,6S,7R)-2-methyl-4-oxatricyclo[5.2.1.02,6]dec-8-en-3-one
• CAS: 67390-36-7；129172-70-9；136459-16-0
• 化学式: C₁₀H₁₂O₂
• 分子量: 164.204
• InChiKey: KZOIESIDADJZCX-PYHGXSLLSA-N

物化性质

• 熔点：
  137-139 °C
• 沸点：
  289.5±39.0 °C(Predicted)
• 密度：
  1.216±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+/-)-(1S*,2R*,6S*,7R*)-2-Methyl-4-oxatricyclo<5.2.1.0^2,6>dec-8-en-3-one 以80%的产率得到3-甲基-2(5H)-呋喃酮
  参考文献：
  名称：

  An Efficient and Short Synthesis of 3-Methyl-2(5H)-Furanone, a Synthon for Strigol Analogues

  摘要：

  A three steps synthesis of 3-methyl-2(5H)-furanone from citraconic anhydride is reported. The furanone is prepared in an overall yield of 60%.

  DOI：

  10.1080/00397919208019280
• 作为产物：
  描述：

  甲基NA酸酐 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以86%的产率得到(+/-)-(1S*,2R*,6S*,7R*)-2-Methyl-4-oxatricyclo<5.2.1.0^2,6>dec-8-en-3-one
  参考文献：
  名称：

  Kayser, Margaret M.; Salvador, Judith; Morand, Peter, Canadian Journal of Chemistry, 1983, vol. 61, p. 439 - 441

  摘要：

  DOI：

文献信息

• A Diels-Alder/Retro-Diels-Alder Approach for the Enantioselective Synthesis of Microbial Butenolides
  作者：Christian A. Citron、Susanne M. Wickel、Barbara Schulz、Siegfried Draeger、Jeroen S. Dickschat

  DOI：10.1002/ejoc.201200991

  日期：2012.10.9

  structures were verified by synthesis of reference compounds through a Diels–Alder/retro-Diels–Alder approach. This synthetic method was also successfully applied in the synthesis of butenolides that are signalling molecules from streptomycetes. For the enantioselective synthesis of these butenolides a modified route including an enantioselective Diels–Alder reaction was used.

  已从内生真菌 Geniculosporium sp. 中鉴定出几种挥发性内酯。从岩蔷薇 Cistus monspeliensis 中分离出来，俗称蒙彼利埃岩蔷薇。通过使用闭环汽提装置从琼脂平板培养物中收集真菌挥发物，并通过 GC-MS 分析顶空提取物。这些内酯的结构是从它们的质谱数据中提出的。通过 Diels-Alder/retro-Diels-Alder 方法合成参考化合物来验证建议的结构。这种合成方法也成功地应用于合成链霉菌信号分子丁烯内酯。对于这些丁烯内酯的对映选择性合成，使用了一种改进的路线，包括对映选择性 Diels-Alder 反应。
• Enzymatic resolution of norbor(NE)nylmethanols in organic media and an application to the synthesis of (+)- and (−)-endo-Norbornene lactone.
  作者：A.J.M. Janssen、A.J.H. Klunder、B. Zwanenburg

  DOI：10.1016/s0040-4020(01)80984-4

  日期：1991.7

  The enzymatic resolution of some norbornene carboxylic acids, norbornenylmethanols and -methylamines was evaluated. The kinetic resolution of norbornyl- and norbornenylmethanols by Porcine Pancreatic Lipase (PPL)-catalyzed transesterification in methyl acetate as the solvent leads to corresponding acetates and remaining methanols both of high enantiomeric purity. A useful application is the synthesis of both enantiomers of endo-norbornene lactone 8n via transesterification of iodolactone 18. The influence of structural variations on the efficiency of the PPL-catalyzed resolution of lactone methanols 21, 23, 25 and 28, at the optimal reaction conditions established for iodolactone 18, was investigated.
• Bis-aluminated triflic amide promoted Diels–Alder reactions of α,β-unsaturated lactones
  作者：Akio Saito、Hikaru Yanai、Takeo Taguchi

  DOI：10.1016/j.tetlet.2004.10.079

  日期：2004.12

  The bis-aluminated triflic amides such as TfN[Al(Me)Cl](2) and TfN[Al(iBU)(2)](2,) which are derived from triffic amide (I mol) and aluminum reagent (2 mol), can efficiently promote the Diels-Alder reaction of alpha, beta-unsaturated lactone derivatives as dienophiles. Selection of the ligand on aluminum of these Lewis acids should be important depending on the combination of dienophile and 1,3-diene. (C) 2004 Elsevier Ltd. All rights reserved.
• KAYSER, M. M.;SALVADOR, J.;MORAND, P., CAN. J. CHEM., 1983, 61, N 3, 439-441
  作者：KAYSER, M. M.、SALVADOR, J.、MORAND, P.

  DOI：——

  日期：——
• Kayser, Margaret M.; Salvador, Judith; Morand, Peter, Canadian Journal of Chemistry, 1983, vol. 61, p. 439 - 441
  作者：Kayser, Margaret M.、Salvador, Judith、Morand, Peter

  DOI：——

  日期：——