4-羟基十二烷酸乙酯 | 433285-37-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 4-羟基十二烷酸乙酯
• 英文名称: 4-Hydroxy-dodecanoic acid ethyl ester
• 英文别名: Ethyl 4-hydroxydodecanoate；ethyl 4-hydroxydodecanoate
• CAS: 433285-37-1
• 化学式: C₁₄H₂₈O₃
• 分子量: 244.375
• InChiKey: WOCQQQTYKNAEKX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  17
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  (±)-二氢-5-辛基-2(3H)-呋喃酮	gamma-dodecalactone	2305-05-7	C12H22O2	198.305

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  4-氧代十二烷酸乙酯	ethyl 4-oxododecanoate	59941-35-4	C14H26O3	242.359

反应信息

• 作为反应物：
  描述：

  4-羟基十二烷酸乙酯 在 chromium(VI) oxide 、 氢氧化钾 作用下， 以 甲醇 、 丙酮 为溶剂， 生成 4-氧代十二酸
  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：

  (±)-二氢-5-辛基-2(3H)-呋喃酮 、 乙醇 在 硫酸 作用下， 以11%的产率得到4-羟基十二烷酸乙酯
  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

• Homoaldol and Aldol Reactions from Common Enolates and Oxiranes: Reaction of Reductively Generated Chromium Enolates through Cationic Rearrangement
  作者：Makoto Hojo、Kyosuke Sakata、Xiamuxikamaer Maimaiti、Junya Ueno、Hisashi Nishikori、Akira Hosomi

  DOI：10.1246/cl.2002.142

  日期：2002.2

  Enolates generated from α-bromo esters by the reduction with “Bu6CrLi3” react with oxiranes to afford γ-hydroxy esters and β-hydroxy esters, depending on the Lewis acid used as a promoter.

  α-溴酯通过用“Bu6CrLi3”还原生成的烯醇化物与环氧乙烷反应生成 γ-羟基酯和 β-羟基酯，这取决于用作促进剂的路易斯酸。
• 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.