(2R,5S)-2,5-dimethyl-δ-valerolactone | 103712-18-1

• 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: (2R,5S)-2,5-dimethyl-δ-valerolactone
• 英文别名: (2R,5S)-2,5-dimethyl-2-ethyl-5-hydroxypentanoic acid lactone；(3R,6S)-3-ethyl-3,6-dimethyloxan-2-one
• CAS: 103712-18-1
• 化学式: C₉H₁₆O₂
• 分子量: 156.225
• InChiKey: HLLNAMSFPNFJAT-IONNQARKSA-N

物化性质

• 沸点：
  230.3±8.0 °C(Predicted)
• 密度：
  0.919±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.13
• 重原子数：
  11.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (2R,5S)-2,5-dimethyl-δ-valerolactone 在 氢氧化钾 作用下， 以 四氢呋喃 为溶剂， 生成 (2R,5S)-2-Ethyl-5-hydroxy-2-methyl-hexanoic acid
  参考文献：
  名称：

  Degradation and absolute configurational assignment to C34-botryococcene

  摘要：

  C34-Botryococcene, the major hydrocarbon constituent of the B race of Botryoeoccus braunii, was degraded by ozonolysis of its dihydro derivative followed by Baeyer-Villiger oxidation to gamma-valerolactone, 2,5-dimethylhexanolactone, and 2-ethyl-2,5-dimethylhexanolactone. These three lactones were correlated with enantiomerically pure, synthesized materials using a progressive induced chemical shift technique with the chiral shift reagent Eu(hfc)3. The lactones were found to possess 4S, 2R,5S, and 2R,5S configurations respectively, thereby specifying a 3S,7S,10R,13S,16S,20S configuration for C34-botryococcene. A biogenesis for botryococcene from 1R,2R,3R presqualene diphosphate is proposed to account for the observed 10R,13S configuration.

  DOI：

  10.1021/jo00044a039
• 作为产物：
  描述：

  28,29-dihydrobotryococcene 在 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 (2R,5S)-2,5-dimethyl-δ-valerolactone
  参考文献：
  名称：

  Degradation and absolute configurational assignment to C34-botryococcene

  摘要：

  C34-Botryococcene, the major hydrocarbon constituent of the B race of Botryoeoccus braunii, was degraded by ozonolysis of its dihydro derivative followed by Baeyer-Villiger oxidation to gamma-valerolactone, 2,5-dimethylhexanolactone, and 2-ethyl-2,5-dimethylhexanolactone. These three lactones were correlated with enantiomerically pure, synthesized materials using a progressive induced chemical shift technique with the chiral shift reagent Eu(hfc)3. The lactones were found to possess 4S, 2R,5S, and 2R,5S configurations respectively, thereby specifying a 3S,7S,10R,13S,16S,20S configuration for C34-botryococcene. A biogenesis for botryococcene from 1R,2R,3R presqualene diphosphate is proposed to account for the observed 10R,13S configuration.

  DOI：

  10.1021/jo00044a039

文献信息

• Braunicene. A novel cyclic C32 isoprenoid from Botryococcus braunii
  作者：Zheng. Huang、C. Dale. Poulter、Fred R. Wolf、Todd C. Somers、James D. White

  DOI：10.1021/ja00220a038

  日期：1988.6
• The absolute configuration of (-)-botryococcene
  作者：James D. White、Todd C. Somers、G. Nagabushana. Reddy

  DOI：10.1021/ja00277a054

  日期：1986.8
• HUANG, ZHENG;POULTER, C. DALE;WOLF, FRED R.;SOMERS, TODD C.;WHITE, JAMES +, J. AMER. CHEM. SOC., 110,(1988) N 12, 3959-3964
  作者：HUANG, ZHENG、POULTER, C. DALE、WOLF, FRED R.、SOMERS, TODD C.、WHITE, JAMES +

  DOI：——

  日期：——