ethyl 14-oxotetradecanoate | 101434-22-4

• 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 14-oxotetradecanoate
• CAS: 101434-22-4
• 化学式: C₁₆H₃₀O₃
• 分子量: 270.412
• InChiKey: NBVXROXODSVXCG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  19
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 14-oxotetradecanoate 在 lithium hydroxide 、 正丁基锂 、 三氟化硼乙醚 、 四丁基氟化铵 、 水 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 20.67h， 生成 (17R,18S,19S,20S,21S,22S)-18,19,20,21,22-Pentakis-benzyloxy-25-((R)-1-tert-butoxycarbonyl-2-methyl-propylcarbamoyl)-17-hydroxy-pentacos-14-ynoic acid
  参考文献：
  名称：

  Stereochemistry of Sagittamide A:  Prediction and Confirmation

  摘要：

  The C5-C10 relative stereochemistry of sagittamide A was predicted, with the use of the (3)J(H,H) profiles assembled from the spin-coupling constants reported in the literature. The predicted relative stereochemistry was then confirmed by a total synthesis of two relevant remote diastereomers. The absolute configuration of sagittamide A was established through a detailed H-1 NMR analysis of the two remote diastereomers, followed by doping experiments of them with the authentic natural product.

  DOI：

  10.1021/ol061582d
• 作为产物：
  描述：

  7-溴庚酸 在 吡啶 、 sodium hypophosphite 、 [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl) palladium(II) dichloride 、 溶剂黄146 、 乙酰氯 、 lithium bromide 作用下， 以 四氢呋喃 、 N-甲基吡咯烷酮 、 水 为溶剂， 反应 24.0h， 生成 ethyl 14-oxotetradecanoate
  参考文献：
  名称：

  Antiproliferative and Antimigratory Actions of Synthetic Long Chain n-3 Monounsaturated Fatty Acids in Breast Cancer Cells That Overexpress Cyclooxygenase-2

  摘要：

  Cyclooxygenase-2 (COX-2) is overexpressed in many human cancers and converts the n-6 polyunsaturated fatty acid (PUFA) arachidonic acid to prostaglandin E-2 (PGE(2)), which drives tumorigenesis; in contrast, n-3 PUFA inhibit tumorigenesis. We tested the hypothesis that these antitumor actions of n-3 PUFA may involve the n-3 olefinic bond. n-3 Monounsaturated fatty acids (MUFAs) of chain length C16-C22 were synthesized and evaluated in MDA-MB-468 breast cancer cells that stably overexpressed COX-2 (MDA-COX-2 cells). Longer chain (C19-C22) n-3 MUFAs inhibited proliferation, activated apoptosis, decreased PGE2 formation, and decreased cell invasion; C16-C18 analogues were less active. Molecular modeling showed that interactions of Arg120, Tyr355, and several hydrophobic amino acid residues in the COX-2 active site with C19-C22 MUFA analogues were favored. Thus, longer-chain n-3 MUFAs may be prototypes of novel anticancer agents that decrease the formation of PGE2 in tumor cells that contain high levels of COX-2.

  DOI：

  10.1021/jm300673z

文献信息

• Bidentate Ligands by Self-Assembly through Hydrogen Bonding: A General Room Temperature/Ambient Pressure Regioselective Hydroformylation of Terminal Alkenes
  作者：Wolfgang Seiche、Alexander Schuschkowski、Bernhard Breit

  DOI：10.1002/adsc.200505174

  日期：2005.10

  room temperature/ambient pressure regioselective hydroformylation of terminal alkenes with low catalyst loadings in good activity. The generality of this catalyst under these conditions was demonstrated for a wide range of structurally diverse alkenes equipped with many important functional groups. Thus, this practical and highly selective hydroformylation protocol, which omits the need for special pressure

  6-DPPon（1）/铑催化剂首次使具有低催化剂负载量且活性良好的末端烯烃在室温/环境压力下进行区域选择性加氢甲酰化。在各种条件下配备许多重要官能团的结构多样的烯烃证明了该催化剂在这些条件下的通用性。因此，这种实用且高度选择性的加氢甲酰化方案无需特殊的压力设备，应在有机合成中得到广泛的应用。
• Stereochemistry of Sagittamide A:  Prediction and Confirmation
  作者：Hirofumi Seike、Indranath Ghosh、Yoshito Kishi

  DOI：10.1021/ol061582d

  日期：2006.8.1

  The C5-C10 relative stereochemistry of sagittamide A was predicted, with the use of the (3)J(H,H) profiles assembled from the spin-coupling constants reported in the literature. The predicted relative stereochemistry was then confirmed by a total synthesis of two relevant remote diastereomers. The absolute configuration of sagittamide A was established through a detailed H-1 NMR analysis of the two remote diastereomers, followed by doping experiments of them with the authentic natural product.
• Antiproliferative and Antimigratory Actions of Synthetic Long Chain n-3 Monounsaturated Fatty Acids in Breast Cancer Cells That Overexpress Cyclooxygenase-2
  作者：Pei H. Cui、Tristan Rawling、Kirsi Bourget、Terry Kim、Colin C. Duke、Munikumar R. Doddareddy、David E. Hibbs、Fanfan Zhou、Bruce N. Tattam、Nenad Petrovic、Michael Murray

  DOI：10.1021/jm300673z

  日期：2012.8.23

  Cyclooxygenase-2 (COX-2) is overexpressed in many human cancers and converts the n-6 polyunsaturated fatty acid (PUFA) arachidonic acid to prostaglandin E-2 (PGE(2)), which drives tumorigenesis; in contrast, n-3 PUFA inhibit tumorigenesis. We tested the hypothesis that these antitumor actions of n-3 PUFA may involve the n-3 olefinic bond. n-3 Monounsaturated fatty acids (MUFAs) of chain length C16-C22 were synthesized and evaluated in MDA-MB-468 breast cancer cells that stably overexpressed COX-2 (MDA-COX-2 cells). Longer chain (C19-C22) n-3 MUFAs inhibited proliferation, activated apoptosis, decreased PGE2 formation, and decreased cell invasion; C16-C18 analogues were less active. Molecular modeling showed that interactions of Arg120, Tyr355, and several hydrophobic amino acid residues in the COX-2 active site with C19-C22 MUFA analogues were favored. Thus, longer-chain n-3 MUFAs may be prototypes of novel anticancer agents that decrease the formation of PGE2 in tumor cells that contain high levels of COX-2.