1-(Tetrahydropyranyloxy)-10-oxoundecane | 162899-34-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 1-(Tetrahydropyranyloxy)-10-oxoundecane
• 英文别名: 11-(Oxan-2-yloxy)undecan-2-one
• CAS: 162899-34-5
• 化学式: C₁₆H₃₀O₃
• 分子量: 270.412
• InChiKey: XNGDEKCWHGCFTP-UHFFFAOYSA-N

物化性质

• 沸点：
  370.4±27.0 °C(predicted)
• 密度：
  0.95±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.94
• 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-(Tetrahydropyranyloxy)-10-oxoundecane 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 生成 3-Oxo-12-(tetrahydro-pyran-2-yloxy)-dodecanoic acid ((S)-2-oxo-tetrahydro-furan-3-yl)-amide
  参考文献：
  名称：

  Synthesis of Pseudomonas quorum-sensing autoinducer analogs and structural entities required for induction of apoptosis in macrophages

  摘要：

  The synthesis of the analogs of N-3-oxododecanoyl-L-homoserine lactone (1) and their structure-activity relationship for the apoptotic induction in macrophages, P388D1 cells, are described. It was revealed that the position of the oxo group in the acyl side chain in addition to the presence of the L-homoserine lactone unit is crucial for the apoptosis-inducing activity. Furthermore, the long acyl side chains with hydrophobic distal ends are preferable for the activity. (C) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.01.054
• 作为产物：
  描述：

  10-十一烯-1-醇 在 chromium(VI) oxide 、 sodium hydroxide 、 高氯酸 、 4-甲基苯磺酸吡啶 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 生成 1-(Tetrahydropyranyloxy)-10-oxoundecane
  参考文献：
  名称：

  Synthesis of Pseudomonas quorum-sensing autoinducer analogs and structural entities required for induction of apoptosis in macrophages

  摘要：

  The synthesis of the analogs of N-3-oxododecanoyl-L-homoserine lactone (1) and their structure-activity relationship for the apoptotic induction in macrophages, P388D1 cells, are described. It was revealed that the position of the oxo group in the acyl side chain in addition to the presence of the L-homoserine lactone unit is crucial for the apoptosis-inducing activity. Furthermore, the long acyl side chains with hydrophobic distal ends are preferable for the activity. (C) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.01.054

文献信息

• Silver-catalyzed cross-coupling reactions of alkyl bromides with alkyl or aryl Grignard reagents
  作者：Hidenori Someya、Hideki Yorimitsu、Koichiro Oshima

  DOI：10.1016/j.tetlet.2009.02.040

  日期：2009.7

  Treatment of secondary or tertiary alkyl bromides with alkyl Grignard reagents in the presence of catalytic amounts of silver bromide and potassium fluoride in CH2Cl2 afforded the corresponding cross-coupling products in reasonable yields. Moreover, silver showed catalytic activity for the cross-coupling reactions of alkyl bromides with aryl Grignard reagents.

  在催化量的溴化银和氟化钾在CH 2 Cl 2中的存在下，用烷基格氏试剂处理仲或叔烷基溴化物，可以合理的收率得到相应的交叉偶联产物。此外，银对于烷基溴与芳基格氏试剂的交叉偶联反应显示出催化活性。
• Preparation of the versatile chiron, (R)- and (S)-12-(tetrahydropyranyloxy)-3-methyldodecan-1-ol: application to the syntheses of methyl branched insect pheromones
  作者：S. Sankaranarayanan、A. Sharma、B. A. Kulkarni、S. Chattopadhyay

  DOI：10.1021/jo00118a047

  日期：1995.6

  A convenient chemoenzymatic synthesis for the title methyl branched chiron has been developed starting from 10-undecenoic acid (1). Thus, 1 was converted to 1-(tetrahydropyranyloxy)-10-undecan-2-one (4) which on reaction with triethyl phosphonoacetate and subsequent functionalization led to the racemic chiron 7. This was resolved via C. rugosa lipase-catalyzed acetylation and subsequently used for the syntheses of some chiral insect pheromones. Thus, (S)-7 was mesylated, reduced with LAH and acetylated to give the pheromone (R)-10-methyldodecan-1-yl acetate (I), while its oxidation to the aldehyde 10 followed by Wittig reaction with methylenephosphorane, depyranylation, and hydrogenation gave the alcohol 12. Its tosylation, detosylation, and Hg2+-catalyzed hydration furnished (R)-10-methyltridecan-2-one (II). Likewise, Wittig reaction of (R)-10 with a suitable phosphorane and similar protocol as above afforded the alcohol 14. Its tosylate was coupled with 3-butenylmagnesium bromide to furnish pheromone (S)-14-methyloctadecene (III).