2-carbethoxy-2-dodecyl-1,3-dithiane | 160941-12-8

• 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: 2-carbethoxy-2-dodecyl-1,3-dithiane
• CAS: 160941-12-8
• 化学式: C₁₉H₃₆O₂S₂
• 分子量: 360.626
• InChiKey: WRPVQGSOSZQPOV-UHFFFAOYSA-N

物化性质

• 沸点：
  446.6±45.0 °C(Predicted)
• 密度：
  1.000±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.43
• 重原子数：
  23.0
• 可旋转键数：
  13.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-carbethoxy-2-dodecyl-1,3-dithiane 在 lithium hydroxide 、 N-溴代丁二酰亚胺(NBS) 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 14.33h， 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：

  1,3-二噻烷-2-甲酸乙酯 、 溴代十二烷 在 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 以93%的产率得到2-carbethoxy-2-dodecyl-1,3-dithiane
  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

文献信息

• 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.