(S)-1,1-diethoxynon-2-yn-4-ol | 156129-57-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (S)-1,1-diethoxynon-2-yn-4-ol
• 英文别名: (-)-(4S)-1,1-diethoxynon-2-yn-4-ol；(4S)-1,1-diethoxynon-2-yn-4-ol
• CAS: 156129-57-6
• 化学式: C₁₃H₂₄O₃
• 分子量: 228.332
• InChiKey: HKKTYOXRKSVGMF-LBPRGKRZSA-N

物化性质

• 沸点：
  326.0±27.0 °C(Predicted)
• 密度：
  0.961±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-1,1-diethoxynon-2-yn-4-ol 在 lithium aluminium tetrahydride 、 硫酸 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 0.52h， 生成 (2E,4S)-4-hydroxy-2-nonenal
  参考文献：
  名称：

  4-Hydroxynon-2-enal, a cytotoxic lipid peroxidation product, and its C5-analog 4-hydroxypent-2-enal: Enantioselective synthesis and stereoanalysis

  摘要：

  A stereoselective synthesis of the lipid peroxidation products 4-hydroxypent-2-enal (1a) and 4-hydroxynon-2-enal (1b) in high optical purity is presented. The configuration of 1a and b was established by Ru(III)-catalyzed oxidative degradation and subsequent stereoanalysis of the resulting alpha-hydroxy acids. It was demonstrated that 1a is configuratively stable under physiological conditions.

  DOI：

  10.1016/s0040-4020(01)81757-9
• 作为产物：
  描述：

  (S)-tert-butyldimethyl(oct-1-yn-3-yloxy)silane 在 六甲基磷酰三胺 、 正丁基锂 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 为溶剂， 反应 5.33h， 生成 (S)-1,1-diethoxynon-2-yn-4-ol
  参考文献：
  名称：

  新的光学活性炔丙基氟化物的合成及其在脂肪酸代谢物的单氟化类似物的对映选择性合成中的应用。

  摘要：

  报道了一种获得具有烯丙基或炔丙基位置的单个氟原子的光学活性不饱和或多不饱和体系的新方法。该策略的核心是在炔丙醇氟化过程中观察到的高度区域和立体控制，可实现短而高效的1合成。此外，简单的官能团转化产生了2和3的烯醛。这三种关键中间体用于制备脂肪酸代谢物的旋光单氟类似物。

  DOI：

  10.1021/jo010056r

文献信息

• Enzymatic resolution of the ethyl acetals of (R)- and (S)-4-hydroxyalk-2-ynals
  作者：Pietro Allevi、Mario Anastasia、Francesco Cajone、Pierangela Ciuffreda、Anna M. Sanvito

  DOI：10.1016/s0957-4166(00)80472-3

  日期：1994.1

  4-hydroxyalk-2-ynals diethylacetals have been efficiently resolved by enatioselective acetylation mediated by Pseudomonas fluorescens lipase affording the acetylated (R)-enantiomers in preference, independent of the length and bulk of the alkyl substituent at the carbinol group. Reduction with LiAlH4 of unreacted or acetylated isomers affords the corresponding ethylenic acetals with the hydrogen deriving from the hydride in the beta position in respect to the allylic hydroxyl.
• Synthesis of New Optically Active Propargylic Fluorides and Application to the Enantioselective Synthesis of Monofluorinated Analogues of Fatty Acid Metabolites
  作者：Michaël Prakesch、Danielle Grée、René Grée

  DOI：10.1021/jo010056r

  日期：2001.5.1

  A new approach to obtain optically active unsaturated or polyunsaturated systems with a single fluorine atom in an allylic or propargylic position is reported. Central to this strategy is the high regio- and stereocontrol observed during the fluorination of propargylic alcohols allowing a short and efficient synthesis of 1. Further, simple functional group transformations gave the enals 2 and 3. These

  报道了一种获得具有烯丙基或炔丙基位置的单个氟原子的光学活性不饱和或多不饱和体系的新方法。该策略的核心是在炔丙醇氟化过程中观察到的高度区域和立体控制，可实现短而高效的1合成。此外，简单的官能团转化产生了2和3的烯醛。这三种关键中间体用于制备脂肪酸代谢物的旋光单氟类似物。
• 4-Hydroxynon-2-enal, a cytotoxic lipid peroxidation product, and its C5-analog 4-hydroxypent-2-enal: Enantioselective synthesis and stereoanalysis
  作者：Gerhard Bringmann、Michael Gassen、Raphaëlle Lardy

  DOI：10.1016/s0040-4020(01)81757-9

  日期：1994.8

  A stereoselective synthesis of the lipid peroxidation products 4-hydroxypent-2-enal (1a) and 4-hydroxynon-2-enal (1b) in high optical purity is presented. The configuration of 1a and b was established by Ru(III)-catalyzed oxidative degradation and subsequent stereoanalysis of the resulting alpha-hydroxy acids. It was demonstrated that 1a is configuratively stable under physiological conditions.