6-octyl-3,4,5,6-tetrahydropyran-2-one | 99461-66-2

• 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: (R)-δ-tridecalactone；δ-tridecalactone；(5R)-tridecan-5-olide；(+)-5-tridecanolide；tridecan-5-olide；5-tridecanolide；5-Tridecanolide, (R)-；(6R)-6-octyloxan-2-one
• CAS: 99461-66-2
• 化学式: C₁₃H₂₄O₂
• 分子量: 212.332
• InChiKey: RZZLMGATMUAJPX-GFCCVEGCSA-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

• 作为反应物：
  描述：

  甲基锂 、 6-octyl-3,4,5,6-tetrahydropyran-2-one 以 乙醚 、 正己烷 为溶剂， 生成 (R)-2-Methyl-tetradecane-2,6-diol
  参考文献：
  名称：

  Asymmetric reduction of the prochiral carbonyl group of aliphatic .gamma.- and .delta.-keto acids by use of fermenting bakers' yeast

  摘要：

  DOI：

  10.1021/jo00228a039
• 作为产物：
  描述：

  5-Oxo-tridecansaeure 在 potassium dihydrogenphosphate 、 baker's yeast 、 葡萄糖 、 magnesium sulfate 作用下， 以 水 为溶剂， 反应 48.0h， 以54%的产率得到6-octyl-3,4,5,6-tetrahydropyran-2-one
  参考文献：
  名称：

  用发酵面包酵母高度对映选择性还原 δ-酮酸。光学纯 (R)-(+)-5-十六内酯的简便合成

  摘要：

  光学纯的 (R)-(+)-十六烷内酯、(+)-5-十三烷内酯和 (+)-5-壬内酯是通过用发酵面包酵母还原相应的 δ-酮酸制备的。

  DOI：

  10.1246/cl.1985.1475

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，
• HIGHLY ENANTIOSELECTIVE REDUCTION OF δ-KETO ACIDS WITH FERMENTING BAKER’S YEAST. A FACILE SYNTHESIS OF OPTICALLY PURE (<i>R</i>)-(+)-5-HEXADECANOLIDE
  作者：Masanori Utaka、Hisashi Watabu、Akira Takeda

  DOI：10.1246/cl.1985.1475

  日期：1985.10.5

  Optically pure (R)-(+)-hexadecanolide, (+)-5-tridecanolide, and (+)-5-nonanolide were prepared from the corresponding δ-keto acids by reduction with fermenting baker’s yeast.

  光学纯的 (R)-(+)-十六烷内酯、(+)-5-十三烷内酯和 (+)-5-壬内酯是通过用发酵面包酵母还原相应的 δ-酮酸制备的。
• Efficient and flexible synthesis of chiral γ- and δ-lactones
  作者：Andreas Habel、Wilhelm Boland

  DOI：10.1039/b801514g

  日期：——

  An efficient and highly flexible synthesis for chiral γ- and δ-lactones with high enantiomeric purity is described (>99% ee and 57–87% overall yield). The protocol involves alkylation of chiral 1,2-oxiranes with terminally unsaturated Grignard reagents. Subsequent oxidative degradation (OsO4–Oxone) of the terminal double bond from chiral alk-1-en-5-ols and alk-1-en-6-ols affords 4- or 5-hydroxy acids and γ- and δ-lactones after acidic workup. The flexibility and efficiency of the protocol is illustrated by the synthesis of several alkanolides and alkenolides, hydroxy fatty acids and dihydroisocoumarins.

  描述了一种高效且高度灵活的合成方法，用于制备具有高对映体纯度的手性γ-和δ-内酯（>99% ee和57–87%总体产率）。该方法涉及用末端不饱和的格氏试剂对手性1,2-氧杂环丁烷进行烷基化。随后，手性alk-1-en-5-醇和alk-1-en-6-醇的末端双键经过氧化降解（OsO4–Oxone），在酸性处理后可得到4-或5-羟基酸以及γ-和δ-内酯。通过合成几种烷醇内酯和烯醇内酯、羟基脂肪酸和二氢异香豆素，展示了该方法的灵活性和高效性。
• Enantioselective Synthesis of <font>δ</font>-Lactones with Lipase-Catalyzed Resolution and Mitsunobu Reaction
  作者：Yasutaka Shimotori、Masakazu Aoyama、Tetsuo Miyakoshi

  DOI：10.1080/00397911.2010.529230

  日期：2012.3.1

  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.
• 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.