2-Oxo-(1S,4R)-cineole | 111536-20-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 2-Oxo-(1S,4R)-cineole
• 英文别名: 2-oxo-1,4-cineole；(1S,4R)-1-methyl-4-propan-2-yl-7-oxabicyclo[2.2.1]heptan-2-one
• CAS: 111536-20-0
• 化学式: C₁₀H₁₆O₂
• 分子量: 168.236
• InChiKey: GCTISMWUJLRZKU-VHSXEESVSA-N

物化性质

• 沸点：
  195-200 °C
• 密度：
  1.089±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 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：

  2-Oxo-(1S,4R)-cineole 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.67h， 生成 2(S)-endo-hydroxy-1(S),4(R)-cineole (R)-(-)-O-acetylmandelate
  参考文献：
  名称：

  Stereochemistry of microbiological hydroxylations of 1,4-cineole

  摘要：

  DOI：

  10.1021/jo00259a017
• 作为产物：
  描述：

  (±)-2-exo-hydroxy-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1 ]heptane 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以70%的产率得到2-Oxo-(1S,4R)-cineole
  参考文献：
  名称：

  Stereochemistry of microbiological hydroxylations of 1,4-cineole

  摘要：

  DOI：

  10.1021/jo00259a017

文献信息

• WEYERSTAHL, PETER;BRENDEL, JOACHIM, LIEBIGS ANN. CHEM.,(1990) N0, C. 1029-1036
  作者：WEYERSTAHL, PETER、BRENDEL, JOACHIM

  DOI：——

  日期：——
• LIU, WEI-GUO;GOSWAMI, ANIMESH;STEFFEK, ROBIN PAULSON;CHAPMAN, ROBERT L.;S+, J. ORG. CHEM., 53,(1988) N 24, C. 5700-5704
  作者：LIU, WEI-GUO、GOSWAMI, ANIMESH、STEFFEK, ROBIN PAULSON、CHAPMAN, ROBERT L.、S+

  DOI：——

  日期：——
• Hydroxylation of deuterated 1,4-cineoles by Bacillus cereus
  作者：Wei Guo Liu、James J. Steffens、Animesh Goswami、John P. N. Rosazza

  DOI：10.1021/jo00075a028

  日期：1993.11

  The stereochemistry and mechanism of 1,4-cineole hydroxylation by the cytochrome P-450-containing strain of Bacillus cereus UI-1477 was examined using specifically deuterated aubstrates. Stereospecifically deuterated 1,4-cineoles were synthesized by Wolff-Kishner reductions of enantiomeric 2-oxo-1,4-cineoles, and by Barton-McCombie elimination of the alcohol functional group of 2-hydroxy-2-deutero-(1R,4S)-cineole. Products obtained from hydroxylations of 2-deutero-(1R,4S)-cineole and enantiomeric 2,2,3,3-tetradeutero- and 2,2,3-trideutero-1,4-cineoles were isolated and characterized by gas chromatography/mass spectrometry and by H-1- and H-2-NMR spectroscopy. Deuterium at the site which is oxygenated does not change hydroxylation stereospecificity, but it dramatically shifts the relative ratios of 2-endo- and 2-exo-alcohol products formed. Analysis of cineole alcohols obtained by microbial hydroxylation of multiply-deuterated-1,4-cineoles indicated that the starting materials contained deuterium at both the 2- and 6-positions, suggesting that a 2,6-proton migration occurs during the Wolff-Kishner reduction of enantiomerically pure 2-oxo-1,4-cineoles. Ratios of cineole alcohols formed from monodeuterated-1,4-cineoles reveal the likehood of a two-step mechanism involving nonspecific hydrogen atom removal followed by stereospecific hydroxylation.