ethyl 2-oxotetradecanoate | 160941-13-9

• 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 2-oxotetradecanoate
• 英文别名: 2-oxo-tetradecanoic acid ethyl ester；Tetradecanoic acid, 2-oxo-, ethyl ester
• CAS: 160941-13-9
• 化学式: C₁₆H₃₀O₃
• 分子量: 270.412
• InChiKey: YNFVBHVDEIFXSY-UHFFFAOYSA-N

物化性质

• 沸点：
  353.0±11.0 °C(Predicted)
• 密度：
  0.922±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  19
• 可旋转键数：
  14
• 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 2-oxotetradecanoate 在 lithium hydroxide 作用下， 以 甲醇 为溶剂， 反应 14.0h， 生成 2-oxotetradecanoic acid
  参考文献：
  名称：

  Synthesis of α-difluoro and α-difluoro-β-trifluoroketo-derivatives as potential inhibitors for Cholesterol Ester Hydrolase

  摘要：

  Pancreatic Cholesterol Ester Hydrolase, a serine esterase, catalyzes the hydrolysis of cholesteryl esters in the gut. We report the convergent synthesis of alpha-difluoro-beta-trinuoroketo-(5,10,15) and of alpha-difluoroketo-derivatives (22,23) as inhibitors of this enzyme that were designed to generate stable tetrahedral reaction intermediates. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00290-9
• 作为产物：
  描述：

  2-carbethoxy-2-dodecyl-1,3-dithiane 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 水 、 丙酮 为溶剂， 反应 0.17h， 以90%的产率得到ethyl 2-oxotetradecanoate
  参考文献：
  名称：

  Synthesis and inhibitory activity of difluoroketone substrate analogs of N-myristoyltransferase.

  摘要：

  Two fluorinated nonhydrolyzable analogs of myristoyl-coenzyme A were synthesized and tested for inhibitory activity against N-myristoyltransferase (NMT). S-(2,2-Difluoro-3-oxohexadecyl)-coenzyme A (3) and S-(3,3-difluoro-2-oxopentadecyl)-coenzyme A (2) were prepared by alkylation of coenzyme A and were purified by reverse phase chromatography. Inhibition of NMT was observed with 3 and 2, with IC50's of 110 nM and 80 nM, respectively, in an in vitro assay developed in our laboratory. The known unfluorinated analog S-(2-oxopentadecyl)-coenzyme A (1) was found to have an IC50 of 7 nM. At 100 mu M in D2O, 3 was 59% hydrated and 2 was 88% hydrated.

  DOI：

  10.1016/s0040-4020(01)89601-0

文献信息

• Chiral <i>N</i>,<i>N′</i>-Dioxide/Lanthanide(III) Complex Catalyzed Asymmetric Bisvinylogous Mukaiyama Aldol Reactions
  作者：Kai Fu、Jingchuan Zhang、Lili Lin、Jun Li、Xiaohua Liu、Xiaoming Feng

  DOI：10.1021/acs.orglett.6b03470

  日期：2017.1.20

  complexes have been developed as efficient catalysts for the bisvinylogous Mukaiyama aldol reaction of silyl ketene acetal with α-ketoesters and aldehydes, respectively. The catalytic systems were highly ε-selective, and the substrate scope was wide. The corresponding ε-hydroxy-α,β,γ,δ-unsaturated esters were obtained in up to 95% yield and 98% ee.

  已开发出手性N，N'-二氧化物/ Y（OTf）3和Sc（OTf）3配合物，分别作为甲硅烷基乙烯酮缩醛与α-酮酸酯和醛类双乙烯基木的Mukaiyama aldol反应的有效催化剂。催化体系具有高度的ε选择性，并且底物范围广。以高达95％的收率和98％的ee获得相应的ε-羟基-α，β，γ，δ-不饱和酯。
• Synthesis and inhibitory activity of difluoroketone substrate analogs of N-myristoyltransferase.
  作者：Karen M. Neder、Stephanie A. French、Stephen P.F. Miller

  DOI：10.1016/s0040-4020(01)89601-0

  日期：1994.1

  Two fluorinated nonhydrolyzable analogs of myristoyl-coenzyme A were synthesized and tested for inhibitory activity against N-myristoyltransferase (NMT). S-(2,2-Difluoro-3-oxohexadecyl)-coenzyme A (3) and S-(3,3-difluoro-2-oxopentadecyl)-coenzyme A (2) were prepared by alkylation of coenzyme A and were purified by reverse phase chromatography. Inhibition of NMT was observed with 3 and 2, with IC50's of 110 nM and 80 nM, respectively, in an in vitro assay developed in our laboratory. The known unfluorinated analog S-(2-oxopentadecyl)-coenzyme A (1) was found to have an IC50 of 7 nM. At 100 mu M in D2O, 3 was 59% hydrated and 2 was 88% hydrated.
• Synthesis of α-difluoro and α-difluoro-β-trifluoroketo-derivatives as potential inhibitors for Cholesterol Ester Hydrolase
  作者：Béatrice David、Francis Schuber

  DOI：10.1016/0960-894x(96)00290-9

  日期：1996.7

  Pancreatic Cholesterol Ester Hydrolase, a serine esterase, catalyzes the hydrolysis of cholesteryl esters in the gut. We report the convergent synthesis of alpha-difluoro-beta-trinuoroketo-(5,10,15) and of alpha-difluoroketo-derivatives (22,23) as inhibitors of this enzyme that were designed to generate stable tetrahedral reaction intermediates. Copyright (C) 1996 Elsevier Science Ltd