(2S,5S)-2,5-dimethyl-δ-valerolactone | 65451-93-6

• 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: (2S,5S)-2,5-dimethyl-δ-valerolactone
• 英文别名: (3S,6S)-3,6-Dimethyltetrahydropyran-2-one；(2S,5S)-trans-2-methyl-5-hexanolide；(2S,5S)-2-methyl-5-hexanolide；(3S,6S)-3,6-dimethyloxan-2-one
• CAS: 65451-93-6
• 化学式: C₇H₁₂O₂
• 分子量: 128.171
• InChiKey: QVPKQLPQAUWJAE-WDSKDSINSA-N

物化性质

• 沸点：
  219.4±8.0 °C(Predicted)
• 密度：
  0.956±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 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：

  (S)-5-(trimethylsilyl)pent-4-yn-2-ol 在 palladium on activated charcoal 正丁基锂 、 4 A molecular sieve 、 四丁基氟化铵 、 氢气 、 potassium carbonate 、 对甲苯磺酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 六甲基磷酰三胺 、 二氯甲烷 、 乙酸乙酯 、 苯 为溶剂， 反应 13.5h， 生成 (2S,5S)-2,5-dimethyl-δ-valerolactone
  参考文献：
  名称：

  The absolute configuration of (-)-botryococcene

  摘要：

  DOI：

  10.1021/ja00277a054

文献信息

• Chiral γ and δ Hydroxysulfones via lipase catalyzed resolutions - synthesis of (R)(+)-4-hexanolide and (2R,5S)-2-methyl-5-hexanolide using intramolecular acylation
  作者：Hollie K. Jacobs、Britta H. Mueller、Aravamudan S. Gopalan

  DOI：10.1016/s0040-4020(01)81988-8

  日期：1992.1

  Lipas PS-30 (Amano) was found to be an effective catalyst for enantioselective transesterification of a number of racemic γ and δ hydroxysulfones with isopropenyl acetate in ether. The intramolecular acylation of the ethyl carbonate derivatives obtained from the chiral hydroxysulfones 1d and 1b has been used for the preparation of R(+)-4-hexanolide, sex pheromone of the female dermestid beetle Trogoderma

  发现Lipas PS-30（Amano）是在醚中将许多外消旋γ和δ羟基砜与乙酸异丙烯酯对映选择性酯交换的有效催化剂。从手性羟基砜1d和1b获得的碳酸乙酯衍生物的分子内酰化已用于制备R（+）-4-己内酯，雌性硬皮甲虫Trogoderma glabrum和（2 R，5 S）- 2-甲基-5-己内酯，木匠蜂的性信息素。
• A Synthesis of Enantiomerically Pure (3<i>S</i>,6<i>R</i>)- and (3<i>R</i>,6<i>S</i>)-3,6-Dimethyltetrahydropyran-2-one
  作者：Rosanna Bernardi、Dario Ghiringhelli

  DOI：10.1055/s-1989-27436

  日期：——

  The title substances (3S,6R)-5 and 3R,6S)-5 were synthesized from enantiomerically pure (R)- and (S)-2-(2-hydroxypropyl)-1,3-dithiane (1), respectively, via a four-step sequence.

  标题物质(3S,6R)-5 和 3R,6S)-5分别由对映体纯度为(R)-和(S)-2-（2-羟基丙基）-1,3-二噻烷（1）通过四步顺序合成。
• The absolute configuration of (-)-botryococcene
  作者：James D. White、Todd C. Somers、G. Nagabushana. Reddy

  DOI：10.1021/ja00277a054

  日期：1986.8
• Addition of organocopper reagents to cyclic sulfites or carbonates of γ,δ-dihydroxy (E)-α,β-enoates
  作者：Suk-Ku Kang、Young-Won Park、Dong-Ha Lee、Hyeong-Su Sim、Jae-Hoon Jeon

  DOI：10.1016/s0957-4166(00)80506-6

  日期：1992.6

  Reaction of cyclic sulfites or carbonates of gamma,delta-dihydroxy (E)-alpha,beta-enoates with R2Cu(CN)Li2, BF3; RCu(CN)Li, BF3 (R = Me-,n-Bu-)afforded either diastereoselective S(N)2' products or reductive elimination product depending on reaction conditions. Addition of R2Cu(CN)Li2, BF3 (R = Me-, n-Bu-) to cyclic sulfite (1) or cyclic carbonate (3) (inverse addition) afforded highly regio-, (E)-stereo- and diastereoselectively alpha-alkylation products (6 and 8). By using this methodology, (2S, 5S)-trans-2-methyl-5-hexanolide, the pheromone of the carpenter bee Xylocopa hirutissima was synthesized.
• Degradation and absolute configurational assignment to C34-botryococcene
  作者：James D. White、Todd C. Somers、G. Nagabushana Reddy

  DOI：10.1021/jo00044a039

  日期：1992.8

  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.