diethyl 2-(5-hydroxypentyl)-2-methylmalonate | 1528636-77-2

• 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: diethyl 2-(5-hydroxypentyl)-2-methylmalonate
• 英文别名: diethyl 2-methyl-2-[5'-hydroxypentyl]malonate；Diethyl 2-(5-hydroxypentyl)-2-methylmalonate；diethyl 2-(5-hydroxypentyl)-2-methylpropanedioate
• CAS: 1528636-77-2
• 化学式: C₁₃H₂₄O₅
• 分子量: 260.331
• InChiKey: JRAXXDGTWOYGMD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.67
• 重原子数：
  18.0
• 可旋转键数：
  9.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  72.83
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  diethyl 2-(5-hydroxypentyl)-2-methylmalonate 在 4-二甲氨基吡啶 、 Kryptofix222[18F]钾盐 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 0.5h， 生成 2-(5-[¹⁸F]fluoropentyl)-2-methylmalonic acid diethyl ester
  参考文献：
  名称：

  Detection of apoptosis by PET/CT with the diethyl ester of [18F]ML-10 and fluorescence imaging with a dansyl analogue

  摘要：

  The diethyl ester of [F-18]ML-10 is a small molecule apoptotic PET probe for cancer studies. Here we report a novel multi-step synthesis of the diethyl ester of ML-10 in excellent yields via fluorination using Xtal-Fluor-E. In addition, a one-pot radiosynthesis of the diethyl ester of [F-18]ML-10 from nucleophilic [F-18]fluoride was completed in 23% radiochemical yield (decay corrected). The radiochemical purity of the product was >= 99%. The diethyl ester of [F-18]ML-10 was used in vivo to detect apoptosis in the testes of mice. In parallel studies, the dansyl-ML-10 diethyl ester was prepared and used to detect apoptotic cells in an in vitro cell based assay. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.11.019
• 作为产物：
  描述：

  diethyl 2-methyl-2-(5-((tetrahydro-2H-pyran-2-yl)oxy)pentyl)malonate 在 4-甲基苯磺酸吡啶 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以85%的产率得到diethyl 2-(5-hydroxypentyl)-2-methylmalonate
  参考文献：
  名称：

  Detection of apoptosis by PET/CT with the diethyl ester of [18F]ML-10 and fluorescence imaging with a dansyl analogue

  摘要：

  The diethyl ester of [F-18]ML-10 is a small molecule apoptotic PET probe for cancer studies. Here we report a novel multi-step synthesis of the diethyl ester of ML-10 in excellent yields via fluorination using Xtal-Fluor-E. In addition, a one-pot radiosynthesis of the diethyl ester of [F-18]ML-10 from nucleophilic [F-18]fluoride was completed in 23% radiochemical yield (decay corrected). The radiochemical purity of the product was >= 99%. The diethyl ester of [F-18]ML-10 was used in vivo to detect apoptosis in the testes of mice. In parallel studies, the dansyl-ML-10 diethyl ester was prepared and used to detect apoptotic cells in an in vitro cell based assay. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.11.019

文献信息

• Catalytic nucleophilic fluorination by an imidazolium ionic liquid possessing trialkylphosphine oxide functionality
  作者：Minakshmi Paramanik、Rekha Singh、Sulekha Mukhopadhyay、Sunil K. Ghosh

  DOI：10.1016/j.jfluchem.2015.06.022

  日期：2015.10

  The synthesis of a new alkylmethylimidazolium ionic liquid wherein the alkyl group is functionalized with dihexylphosphine oxide moiety at the terminal position has been achieved in four steps from 1-methylimidazole. This hybrid ionic liquid effectively catalyzed the nucleophilic fluorination of primary alkyl mesylates under mild conditions using CsF as the fluoride source with a faster rate compared

  从1-甲基咪唑通过四个步骤已经完成了新的烷基甲基咪唑鎓离子液体的合成，其中烷基在末端位置被二己基膦氧化物部分官能化。与丁基甲基咪唑鎓甲磺酸盐相比，该杂化离子液体在温和条件下使用CsF作为氟化物源，可有效催化伯烷基甲磺酸酯的亲核氟化反应。将杂化催化剂再循环5次，而不会损害产物的产率和纯度。的亲核氟化已经用于二的合成2-（5-氟戊基）-2-甲基丙二酸二乙酯，的前体18的细胞凋亡显像剂F的同位素和保护形式ø - （2'-氟乙基） -升-酪氨酸肿瘤显像剂的18 F同位素。
• Detection of apoptosis by PET/CT with the diethyl ester of [18F]ML-10 and fluorescence imaging with a dansyl analogue
  作者：Manikandan Kadirvel、Michael Fairclough、Christopher Cawthorne、Emily J. Rowling、Muhammad Babur、Adam McMahon、Paul Birkket、Alison Smigova、Sally Freeman、Kaye J. Williams、Gavin Brown

  DOI：10.1016/j.bmc.2013.11.019

  日期：2014.1

  The diethyl ester of [F-18]ML-10 is a small molecule apoptotic PET probe for cancer studies. Here we report a novel multi-step synthesis of the diethyl ester of ML-10 in excellent yields via fluorination using Xtal-Fluor-E. In addition, a one-pot radiosynthesis of the diethyl ester of [F-18]ML-10 from nucleophilic [F-18]fluoride was completed in 23% radiochemical yield (decay corrected). The radiochemical purity of the product was >= 99%. The diethyl ester of [F-18]ML-10 was used in vivo to detect apoptosis in the testes of mice. In parallel studies, the dansyl-ML-10 diethyl ester was prepared and used to detect apoptotic cells in an in vitro cell based assay. (C) 2013 Elsevier Ltd. All rights reserved.