6-octyl-3,4,5,6-tetrahydropyran-2-one | 124330-64-9

• 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: 6-octyl-3,4,5,6-tetrahydropyran-2-one
• 英文别名: (S)-6-n-octyltetrahydropyran-2-one；(S)-δ-tridecalactone；δ-tridecalactone；tridecan-5-olide；5-tridecanolide；5-Tridecanolide, (S)-；(6S)-6-octyloxan-2-one
• CAS: 124330-64-9
• 化学式: C₁₃H₂₄O₂
• 分子量: 212.332
• InChiKey: RZZLMGATMUAJPX-LBPRGKRZSA-N

物化性质

• 沸点：
  309.1±10.0 °C(Predicted)
• 密度：
  0.920±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 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：

  [(5S)-1-(methylamino)-1-oxotridecan-5-yl] acetate 在 对甲苯磺酸 、 sodium hydroxide 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 27.0h， 生成 6-octyl-3,4,5,6-tetrahydropyran-2-one
  参考文献：
  名称：

  Enantioselective Synthesis of δ-Lactones with Lipase-Catalyzed Resolution and Mitsunobu Reaction

  摘要：

  Both enantiomers of a series of delta-lactones (e.g., delta-decalactone, delta-dodelactone, and delta-hexadecalactone) were synthesized stereoselectively by Novozym 435-catalyzed resolution. Furthermore, only (S)-enantiomers of delta-lactones were synthesized with a combination of Novozym 435-catalyzed resolution and Mitsunobu reaction.

  DOI：

  10.1080/00397911.2010.529230

文献信息

• Stereoselective Synthesis of δ-Lactones from 5-Oxoalkanals via One-Pot Sequential Acetalization, Tishchenko Reaction, and Lactonization by Cooperative Catalysis of Samarium Ion and Mercaptan
  作者：Jue-Liang Hsu、Jim-Min Fang

  DOI：10.1021/jo016058t

  日期：2001.12.1

  sequence of acetalization, Tishchenko reaction and lactonization. The deliberative use of mercaptan, by comparison with alcohol, is advantageous to facilitate the catalytic cycle. The reaction mechanism and stereochemistry are proposed and supported by some experimental evidence. Such samarium ion/mercaptan cocatalyzed reactions show the feature of remote control, which is applicable to the asymmetric synthesis

  通过sa离子和硫醇的协同催化，一系列5-氧代烷醛以有效和立体选择性的方式转化为（取代的）δ-内酯。这一一锅法包括一系列缩醛化，Tishchenko反应和内酯化。与醇相比，有意使用硫醇有利于促进催化循环。提出了反应机理和立体化学，并得到了一些实验证据的支持。sa离子/硫醇共催化反应显示出远程控制的特征，适用于旋光性δ-内酯的不对称合成。这项研究还证明了两种昆虫信息素（2S，5R）-2-甲基己内酯和（R）-十六烷内酯的合成，
• Cooperative Catalysis of Samarium Diiodide and Mercaptan in a Stereoselective One-Pot Transformation of 5-Oxopentanals into δ-Lactones
  作者：Jue-Liang Hsu、Chao-Tsen Chen、Jim-Min Fang

  DOI：10.1021/ol9911526

  日期：1999.12.1

  [GRAPHICS]We demonstrate a general method for conversion of various 5-oxopentanals to substituted delta-lactones and 1-oxa-2-decalones by the synergistic catalysis of samarium diiodide and 2-propanethiol (or disulfide), The deliberate use of mercaptan is advantageous to facilitate the catalytic cycle, This method shows high stereoselectivities, and an enantioselective procedure is feasible by using the chiral mercaptan (1R,2S)-1 phenyl-2-(N-acetamido)propanethiol as a promoter.
• Enzyme assisted synthesis of enantiomerically pure δ-lactones
  作者：Bernhard Haase、Manfred P. Schneider

  DOI：10.1016/s0957-4166(00)80146-9

  日期：1993.5

  Both enantiomeric series of a wide variety of optically pure 6-alkylated delta-lactones - saturated as well as unsaturated - were prepared via an enzyme mediated route. The key reaction step is the nucleophilic ring opening of enantiomerically pure alkyl-oxiranes, accessible via the corresponding beta-hydroxythioethers which can be obtained enantiomerically pure via enzyme catalyzed kinetic resolutions.
• Gadnon, Rene; Grogan, Gideon; Levitt, Melissa S., Journal of the Chemical Society. Perkin transactions I, 1994, # 18, p. 2537 - 2544
  作者：Gadnon, Rene、Grogan, Gideon、Levitt, Melissa S.、Roberts, Stanley M.、Wan, Peter W. H.、Willetts, Andrew J.

  DOI：——

  日期：——
• Enantio- and Regioselective Baeyer−Villiger Oxidations of 2- and 3-Substituted Cyclopentanones Using Engineered Bakers' Yeast
  作者：Margaret M. Kayser、Gang Chen、Jon D. Stewart

  DOI：10.1021/jo980737v

  日期：1998.10.1