11-(Oxan-2-yloxy)undecan-2-ol | 162899-33-4

• 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: 11-(Oxan-2-yloxy)undecan-2-ol
• CAS: 162899-33-4
• 化学式: C₁₆H₃₂O₃
• 分子量: 272.428
• InChiKey: YYNHAEUJGFUBJE-UHFFFAOYSA-N

物化性质

• 沸点：
  376.0±27.0 °C(Predicted)
• 密度：
  0.95±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  19
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  11-(Oxan-2-yloxy)undecan-2-ol 在 chromium(VI) oxide 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 生成 12-(oxan-2-yloxy)-3-oxododecanoic acid
  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 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 为溶剂， 生成 11-(Oxan-2-yloxy)undecan-2-ol
  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

• 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).
• Synthesis of Pseudomonas quorum-sensing autoinducer analogs and structural entities required for induction of apoptosis in macrophages
  作者：Manabu Horikawa、Kazuhiro Tateda、Etsu Tuzuki、Yoshikazu Ishii、Chihiro Ueda、Tohru Takabatake、Shinichi Miyairi、Keizou Yamaguchi、Masaji Ishiguro

  DOI：10.1016/j.bmcl.2006.01.054

  日期：2006.4

  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.