ethyl 5-oxododecanoate | 103897-43-4

• 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: ethyl 5-oxododecanoate
• CAS: 103897-43-4
• 化学式: C₁₄H₂₆O₃
• 分子量: 242.359
• InChiKey: LWMPEVJJYUOAMX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.65
• 重原子数：
  17.0
• 可旋转键数：
  11.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  ethyl 5-oxododecanoate 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 以75%的产率得到5-氧代十二烷酸
  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：

  ethyl 5-hydroxydodecanoate 在 chromium(VI) oxide 作用下， 以 丙酮 为溶剂， 以81%的产率得到ethyl 5-oxododecanoate
  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

• Generation of 2-Carboethoxyethylzinc iodide and 3-carboethoxypropylzinc iodide and their application to the synthesis of γ- and δ-keto esters
  作者：Yoshinao Tamaru、Hirofumi Ochiai、Tatsuya Nakamura、Kazunori Tsubaki、Zen-ichi Yoshida

  DOI：10.1016/s0040-4039(01)80887-x

  日期：——

  generated by the reaction of the corresponding iodoesters with Zn-Cu couple and utilized for the palladium catalyzed coupling reaction with acid chloride to quantitatively provide gamma- and delta- keto esters, respectively.

  通过相应的碘代酯与Zn-Cu对的反应生成2-羰基乙氧基乙基碘化锌和3-羰基乙氧基丙基碘化锌，并用于钯与酰氯的偶合反应，从而分别定量地提供γ-和δ-酮酸酯。
• TAMARU, YOSHINAO;OCHIAI, HIROFUMI;NAKAMURA, TATSUYA;TSUBAKI, KAZUNORI;YOS+, TETRAHEDRON LETT., 1985, 26, N 45, 5559-5562
  作者：TAMARU, YOSHINAO、OCHIAI, HIROFUMI、NAKAMURA, TATSUYA、TSUBAKI, KAZUNORI、YOS+

  DOI：——

  日期：——
• 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.