1,1-diethoxynon-2-yn-4-one | 122077-89-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,1-diethoxynon-2-yn-4-one
• 英文别名: 2-Nonyn-4-one, 1,1-diethoxy-
• CAS: 122077-89-8
• 化学式: C₁₃H₂₂O₃
• 分子量: 226.316
• InChiKey: AMDZDNYUQGTRPQ-UHFFFAOYSA-N

物化性质

• 沸点：
  290.4±50.0 °C(Predicted)
• 密度：
  0.956±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,1-diethoxynon-2-yn-4-one 在 lithium aluminium tetrahydride 、 (S)-BINAL-H 、 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：

  (+/-)-4-hydroxynon-2-ynal diethyl acetal 在 重铬酸吡啶 、 3 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 以87%的产率得到1,1-diethoxynon-2-yn-4-one
  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

文献信息

• Synthesis of new difluoroalkyl propargylic ketones and their use for the preparation of fluorinated heterocycles
  作者：Pierre Bannwarth、Danielle Grée、René Grée

  DOI：10.1016/j.tetlet.2010.02.116

  日期：2010.5

  Synthetic methodology studies are reported towards the preparation of new propargylic ketones with CF2R side chains. These molecules are used for the synthesis of various types of five- or six-membered heterocycles with difluoroalkyl side chains.

  据报道，合成方法学研究旨在制备带有CF 2 R侧链的新的炔丙基酮。这些分子用于合成具有二氟烷基侧链的各种类型的五元或六元杂环。
• A New Method for the Preparation of (E)-3-Acylprop-2-enoic Acids
  作者：Daniel Obrecht、Bettina Weiss

  DOI：10.1002/hlca.19890720115

  日期：1989.2.1

  A new method for the preparation of (E)-3-acylprop-2-enoic acids ( = (E)-3-acylacrylic acids) of type IIvia acid-catalyzed isomerization of the corresponding 3-acylprop-2-ynal acetals of type I (Scheme 1) has been found. The described reaction gives a rapid and quite general access to these compounds known to exhibit a number of interesting biological activities. Some studies toward the elucidation

  用于制备的新方法（ê）-3- acylprop -2-烯酸酸（=（Ë）-3- acylacrylic氨基酸）类型II通过的相应的3- acylprop -2-炔醛缩醛的酸催化的异构化已找到类型I（方案1）。所描述的反应使人们能够快速而普遍地获得已知表现出许多令人感兴趣的生物活性的这些化合物。已经对阐明反应机理进行了一些研究，并提出了一种假设机理。
• A Novel Approach towards 2,3,5-Trisubstituted Thiophenesvia tandemMichael addition/intramolecularKnoevenagel condensation
  作者：Daniel Obrecht、Fernand Gerber、Daniel Sprengeir、Thierry Masquelin

  DOI：10.1002/hlca.19970800217

  日期：1997.3.24

  easily available, highly functionalized acetylenic ketories 4a–i (Scheme 1), novel 2,3,5-trisubstituted thiophenes 1a–i (Scheme 2) were synthesized in good yields using a tandem Michael-addition/intramolecular Knoevenagel-condensation strategy, featuring Cs2CO3/MgSO4 (1:2) as an efficient base to effect the cyclization. Subsequent simple one-step transformations yielded 2,3-disubstituted thiophene-5-carbaidehydes

  从容易得到的起始，高功能化的炔属ketories 4A-I （方案1），新颖的2,3,5-三取代的噻吩1A-I （方案2）以良好的收率使用串联合成迈克尔-addition /分子内的Knoevenagel -condensation该策略以Cs 2 CO 3 / MgSO 4（1：2）作为有效环化的有效碱。随后的简单一步转化即可生成2,3-二取代的噻吩-5-碳酸酐7a–c，羧酸衍生物8、9和11，以及醇10（方案3）。这些分子构成了有趣的新型含噻吩结构单元，可用于通过组合化学和平行化学技术制备低分子量化合物文库。
• Flexible Synthesis of Pyrimidines with Chiral Monofluorinated and Difluoromethyl Side Chains
  作者：Pierre Bannwarth、Alain Valleix、Danielle Grée、René Grée

  DOI：10.1021/jo900674u

  日期：2009.6.19

  Chiral pyrimidines with a fluorine atom in the benzylic position are easily accessible in high enantiomeric excesses from optically active propargylic intermediates by two complementary routes. Both the use of optically active propargylic fluorides and the fluorination of the chiral pyrimidine in the final stage give excellent results in terms of enantiocontrol. On the other hand, original pyrimidines with a difluoromethyl side chain are also obtained in a few steps from new propargylic ketones bearing a CHF2 substituent on the triple bond.
• OBRECHT, DANIEL;WEISS, BETTINA, HELV. CHIM. ACTA., 72,(1989) N, C. 117-122
  作者：OBRECHT, DANIEL、WEISS, BETTINA

  DOI：——

  日期：——