(14R)-17-羟基-1-[2-(碘125)-4-[3-(三氟甲基)-3H-双吖丙啶-3-基]苯基]-N,N,N-三甲基-3,12-二氧代-14-[[(1-氧代十六烷基)氧基]甲基]-2,13,16,18-四氧杂-17-磷杂二十烷-20-铵内盐17-氧化物 | 156996-76-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油磷脂
• 中文名称: (14R)-17-羟基-1-[2-(碘125)-4-[3-(三氟甲基)-3H-双吖丙啶-3-基]苯基]-N,N,N-三甲基-3,12-二氧代-14-[[(1-氧代十六烷基)氧基]甲基]-2,13,16,18-四氧杂-17-磷杂二十烷-20-铵内盐17-氧化物
• 英文名称: 1-O-hexadecanoyl-2-O-<9-<<<2-(125I)iodo-4-((trifluoromethyl)-3H-diazirin-3-yl)benzyl>oxy>carbonyl>nonanoyl>-sn-glycero-3-phosphocholine
• 英文别名: I-Tid-PC-16；[(2R)-3-hexadecanoyloxy-2-[10-[[2-(125I)iodanyl-4-[3-(trifluoromethyl)diazirin-3-yl]phenyl]methoxy]-10-oxodecanoyl]oxypropyl] 2-(trimethylazaniumyl)ethyl phosphate
• CAS: 156996-76-8
• 化学式: C₄₃H₇₀F₃IN₃O₁₀P
• 分子量: 1002.01
• InChiKey: ARMUBPQMRBSKNL-ZRKYHJCISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.9
• 重原子数：
  61
• 可旋转键数：
  39
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  162
• 氢给体数：
  0
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  1-O-hexadecanoyl-2-O-<9-<<<2-(tributylstannyl)-4-<(trifluoromethyl)-3H-diazirin-3-yl>benzyl>oxy>carbonyl>nonanoyl>-sn-glycero-3-phosphpcholine 在 过氧乙酸 、 sodium iodide 作用下， 以 溶剂黄146 为溶剂， 反应 0.03h， 以40%的产率得到(14R)-17-羟基-1-[2-(碘125)-4-[3-(三氟甲基)-3H-双吖丙啶-3-基]苯基]-N,N,N-三甲基-3,12-二氧代-14-[[(1-氧代十六烷基)氧基]甲基]-2,13,16,18-四氧杂-17-磷杂二十烷-20-铵内盐17-氧化物
  参考文献：
  名称：

  2-(Tributylstannyl)-4-[3-(trifluoromethyl)-3H-diazirin-3-yl]benzyl Alcohol: A Building Block for Photolabeling and Crosslinking Reagents of Very High Specific Radioactivity

  摘要：

  A general approach for the synthesis of novel, radioiodinated photolabeling and cross-linking reagents at no-carrier-added (nea) specific radioactivity (> 2000 Ci/mmol) is described. In this approach, 2-(tributylstannyl)-4-[3-(trifluoromethyl)-3H-diazirin-3-yl]benzyl alcohol 12 serves as a module which, through acylation of its alcohol function, is connected to other structural/functional elements to make the tin-containing precursor forms of the reagents. The final, radioactive compounds are then conveniently prepared in yields varying from 15-50% by electrophilic aromatic substitution of the tributylstannyl group by I-125(+) generated in situ from I-125(-) by peracetic acid. Using this approach, we have synthesized two analogues of phosphatidylcholine (PC) (20 and 21), an analogue of ceramide (36), as well as two heterobifunctional label-transfer cross-linkers (29 and 33). PC 21, examined more closely, is a substrate of the PC-specific phospholipid exchange protein from beef liver and of phospholipase D from cabbage. The latter was utilized to enzymatically convert PC 21 into two additional phospholipids, phosphatidylserine (PS) 25 and phosphatidic acid (PA) 26. Reagents that contain this iodinated photophor also combine desirable photochemical properties. Thus, evidence is presented that they undergo efficient photolysis to generate a (singlet) carbene intermediate which inserts efficiently into hydrocarbon CH bonds. In addition, we demonstrate that the diazirine can be photolyzed in a selective manner, that is, without photodeiodination to occur to a significant extent.

  DOI：

  10.1021/ja00116a013