propan-2-yl 12-ethylsulfanyl-12-oxododec-10-enoate | 1246746-99-5

• 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: propan-2-yl 12-ethylsulfanyl-12-oxododec-10-enoate
• CAS: 1246746-99-5
• 化学式: C₁₇H₃₀O₃S
• 分子量: 314.489
• InChiKey: BQLZAYPTBYLJJE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.89
• 重原子数：
  21.0
• 可旋转键数：
  12.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  propan-2-yl 12-ethylsulfanyl-12-oxododec-10-enoate 、 甲基溴化镁 在 C₃₆H₄₄FeP₂*BrCu 作用下， 以 甲基叔丁基醚 为溶剂， 以85%的产率得到propan-2-yl (10S)-12-ethylsulfanyl-10-methyl-12-oxododecanoate
  参考文献：
  名称：

  Asymmetric synthesis and structure elucidation of a glycerophospholipid from Mycobacterium tuberculosis

  摘要：

  A glycerophospholipid (1-O-tuberculostearoyl-2-O -palmitoyl-sn-glycero-3-phosphoethanolamine) from Mycobacterium tuberculosis was isolated from the reference strain H37Rv. The molecular structure of this tuberculostearoyl [(R)-10-methyloctadecyl] and palmitoyl containing phosphatidylethanolamine (PE) has been resolved. The substitution pattern on the glycerol backbone could be determined by comparison of the isolate to the two synthetically prepared regioisomers. MS/MS analysis was used to determine its molecular structure. Production of this synthetic version of mycobacterial PE in high yield, with a stereochemically correct and pathogen-specific fatty acyl group, can be used as a standard in LC-MS based lipidomic analyses to detect trace amounts of mycobacterial PE in human blood, sputum, or tissues as a marker of infection by mycobacteria.-ter Horst, B., C. Seshadri, L. Sweet, D. C. Young, B. L. Feringa, D. B. Moody, and A. J. Minnaard. Asymmetric synthesis and structure elucidation of a glycerophospholipid from Mycobacterium tuberculosis. J. Lipid Res. 2010. 51: 1017-1022.

  DOI：

  10.1194/jlr.m001982
• 作为产物：
  描述：

  S-ethyl 2-propenethioate 、 十一碳烯酸异丙酯 在 Hoveyda-Grubbs catalyst second generation 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以92%的产率得到propan-2-yl 12-ethylsulfanyl-12-oxododec-10-enoate
  参考文献：
  名称：

  Asymmetric synthesis and structure elucidation of a glycerophospholipid from Mycobacterium tuberculosis

  摘要：

  A glycerophospholipid (1-O-tuberculostearoyl-2-O -palmitoyl-sn-glycero-3-phosphoethanolamine) from Mycobacterium tuberculosis was isolated from the reference strain H37Rv. The molecular structure of this tuberculostearoyl [(R)-10-methyloctadecyl] and palmitoyl containing phosphatidylethanolamine (PE) has been resolved. The substitution pattern on the glycerol backbone could be determined by comparison of the isolate to the two synthetically prepared regioisomers. MS/MS analysis was used to determine its molecular structure. Production of this synthetic version of mycobacterial PE in high yield, with a stereochemically correct and pathogen-specific fatty acyl group, can be used as a standard in LC-MS based lipidomic analyses to detect trace amounts of mycobacterial PE in human blood, sputum, or tissues as a marker of infection by mycobacteria.-ter Horst, B., C. Seshadri, L. Sweet, D. C. Young, B. L. Feringa, D. B. Moody, and A. J. Minnaard. Asymmetric synthesis and structure elucidation of a glycerophospholipid from Mycobacterium tuberculosis. J. Lipid Res. 2010. 51: 1017-1022.

  DOI：

  10.1194/jlr.m001982