tetradecanoic acid 2,2-dimethyl-1,3-dioxolan-4-ylmethyl ester | 163432-14-2

• 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: tetradecanoic acid 2,2-dimethyl-1,3-dioxolan-4-ylmethyl ester
• 英文别名: 1-myristoyl-2,3-isopropylidene-sn-glycerol；[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl tetradecanoate
• CAS: 163432-14-2
• 化学式: C₂₀H₃₈O₄
• 分子量: 342.519
• InChiKey: PYLQQVMOUCHKEQ-GOSISDBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  24
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tetradecanoic acid 2,2-dimethyl-1,3-dioxolan-4-ylmethyl ester 在 palladium on activated charcoal 吡啶 、 4-二甲氨基吡啶 、 氢气 、 氟化氢吡啶 、 溶剂黄146 、 三乙胺 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 、 三氯氧磷 、 亚硝酸异戊酯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 87.25h， 生成 1-tetradecanoic acid 3-({[(N,N,N-trimethylammonio)ethoxy]hydroxyphosphoryl}oxy)-2-({12-[2-(4-diazocyclohexa-2,5-dienonyl)methylenoxy]dodecanoyl}oxy)propyl ester
  参考文献：
  名称：

  Synthesis and Properties of Photoactivatable Phospholipid Derivatives Designed To Probe the Membrane-Associate Domains of Proteins

  摘要：

  The total syntheses of photoactivatable phospholipidic probes 1 and 2 are described. These probes contain either an aryldiazonium function at their polar head (probes la and Ib) or an diazocyclohexadienonyl group attached to the end of one fatty acid side chain (probe 2) and have been designed to probe the lipid/water interface and the hydrophobic core of the membrane, respectively. The synthetic schemes include the possibility of incorporating a radio-labeled atom (tritium) for further labeling investigations. Both probes were stable in the dark under physiological conditions and could be efficiently photodecomposed at wavelengths above 300 nm, leading to the generation of highly reactive species, aryl cations and cyclohexadienonyl carbene, respectively. In addition, these probes displayed UV-absorption spectra which are compatible with tryptophan-mediated energy transfer photoactivation, which can lead potentially to an efficient mapping of the membrane-associate protein domains.

  DOI：

  10.1021/jo951350k
• 作为产物：
  描述：

  肉豆蔻酸 、 (R)-(-)-甘油醇缩丙酮 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以91%的产率得到tetradecanoic acid 2,2-dimethyl-1,3-dioxolan-4-ylmethyl ester
  参考文献：
  名称：

  环磷脂酸的合成和水解稳定性：对合成和原始细胞研究的影响

  摘要：

  环磷脂酸 (cPA) 是具有治疗潜力的生物活性化合物，但供不应求。我们描述了采用有效的环磷酸化程序的 cPA 的稳健合成，并报告了它们的水解特性——这应该有助于研究它们的生物学特性以及作为合理的原始细胞和合成细胞成分。

  DOI：

  10.1039/d2cc00292b

文献信息

• Synthesis of two new phospholipidic fluorescent probes for membrane studies
  作者：Jean-Philippe Starck、Yoichi Nakatani、Guy Ourisson

  DOI：10.1016/0040-4020(95)00011-v

  日期：1995.2

  Two new fluorenyl-phospholipidic probes have been prepared in good yield by a Pd-0/CuI-catalyzed cross-coupling reaction.
• Synthesis and Properties of Photoactivatable Phospholipid Derivatives Designed To Probe the Membrane-Associate Domains of Proteins
  作者：Marie-Lyne Alcaraz、Ling Peng、Philippe Klotz、Maurice Goeldner

  DOI：10.1021/jo951350k

  日期：1996.1.1

  The total syntheses of photoactivatable phospholipidic probes 1 and 2 are described. These probes contain either an aryldiazonium function at their polar head (probes la and Ib) or an diazocyclohexadienonyl group attached to the end of one fatty acid side chain (probe 2) and have been designed to probe the lipid/water interface and the hydrophobic core of the membrane, respectively. The synthetic schemes include the possibility of incorporating a radio-labeled atom (tritium) for further labeling investigations. Both probes were stable in the dark under physiological conditions and could be efficiently photodecomposed at wavelengths above 300 nm, leading to the generation of highly reactive species, aryl cations and cyclohexadienonyl carbene, respectively. In addition, these probes displayed UV-absorption spectra which are compatible with tryptophan-mediated energy transfer photoactivation, which can lead potentially to an efficient mapping of the membrane-associate protein domains.
• Synthesis and hydrolytic stability of cyclic phosphatidic acids: implications for synthetic- and proto-cell studies
  作者：Veronica Egas Ortuno、Sunil Pulletikurti、Kollery S. Veena、Ramanarayanan Krishnamurthy

  DOI：10.1039/d2cc00292b

  日期：——

  Cyclic phosphatidic acids (cPAs) are bioactive compounds with therapuetic potential, but are in short supply. We describe a robust synthesis of cPAs employing an efficient cyclophosphorylation procedure and report on their hydrolytic properties – which should facilitate the study of their biological properties and as plausible proto- and synthetic-cell components.

  环磷脂酸 (cPA) 是具有治疗潜力的生物活性化合物，但供不应求。我们描述了采用有效的环磷酸化程序的 cPA 的稳健合成，并报告了它们的水解特性——这应该有助于研究它们的生物学特性以及作为合理的原始细胞和合成细胞成分。