(S)-4-<(3,4-Dimethoxybenzyloxy)methyl>-2,2-dimethyl-1,3-dioxolane | 139115-86-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-4-<(3,4-Dimethoxybenzyloxy)methyl>-2,2-dimethyl-1,3-dioxolane
• 英文别名: (S)-4-(((3,4-dimethoxybenzyl)oxy)methyl)-2,2-dimethyl-1,3-dioxolane；4-(S)-(((3,4-dimethoxybenzyl)oxy)methyl)-2,2-dimethyl-1,3-dioxolane；(S)-4-[(3,4-Dimethoxybenzyloxy)methyl]-2,2-dimethyl-1,3-dioxolane；(4S)-4-[(3,4-dimethoxyphenyl)methoxymethyl]-2,2-dimethyl-1,3-dioxolane
• CAS: 139115-86-9
• 化学式: C₁₅H₂₂O₅
• 分子量: 282.337
• InChiKey: HHFQZQLGNIUCFM-LBPRGKRZSA-N

物化性质

• 沸点：
  368.1±37.0 °C(Predicted)
• 密度：
  1.078±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-4-<(3,4-Dimethoxybenzyloxy)methyl>-2,2-dimethyl-1,3-dioxolane 在 吡啶 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 51.0h， 生成 [(2S)-3-[(3,4-dimethoxyphenyl)methoxy]-2-hexadecanoyloxypropyl] hexadecanoate
  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：

  (S)-(+)-1,2-异亚丙基甘油 、 3,4-二甲氧基苄氯 在 六甲基磷酰三胺 、 sodium hydride 作用下， 生成 (S)-4-<(3,4-Dimethoxybenzyloxy)methyl>-2,2-dimethyl-1,3-dioxolane
  参考文献：
  名称：

  设计用于蛋白质二维结晶的类固醇激素衍生物相关的新磷脂的合成

  摘要：

  据报道，合理设计用于孕酮和雌二醇受体的二维结晶的磷脂1 n - 3 n的合成。这些脂质的结构为它们提供了必要的特性，例如当在空气/ H 2 O界面扩散为单层时的流动性和稳定性，对要结晶的蛋白质的亲和力以及脂质单层下配体的可及性。

  DOI：

  10.1002/hlca.19910740810

文献信息

• Synthesis of New Phospholipids Linked to Steroid-Hormone Derivatives Designed for Two-Dimensional Crystallization of Proteins
  作者：Luc Lebeau、Pierre Oudet、Charles Mioskowski

  DOI：10.1002/hlca.19910740810

  日期：1991.12.11

  The synthesis of phospholipids 1n–3n, rationally designed for two-dimensional crystallization of progesterone and estradiol receptors, is reported. The structure of these lipids provides them with essential properties such as fluidity and stability when spread into monolayers at the air/H2O interface, affinity for the protein to be crystallized, and accessibility of the ligand under the lipid monolayer

  据报道，合理设计用于孕酮和雌二醇受体的二维结晶的磷脂1 n - 3 n的合成。这些脂质的结构为它们提供了必要的特性，例如当在空气/ H 2 O界面扩散为单层时的流动性和稳定性，对要结晶的蛋白质的亲和力以及脂质单层下配体的可及性。
• 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.
• Identification of CDP-Archaeol Synthase, a Missing Link of Ether Lipid Biosynthesis in Archaea
  作者：Samta Jain、Antonella Caforio、Peter Fodran、Juke S. Lolkema、Adriaan J. Minnaard、Arnold J.M. Driessen

  DOI：10.1016/j.chembiol.2014.07.022

  日期：2014.10

  Archaeal membrane lipid composition is distinct from Bacteria and Eukarya, consisting of isoprenoid chains etherified to the glycerol carbons. Biosynthesis of these lipids is poorly understood. Here we identify and characterize the archaeal membrane protein CDP-archaeol synthase (CarS) that catalyzes the transfer of the nucleotide to its specific archaeal lipid substrate, leading to the formation of a CDP-activated precursor (CDP-archaeol) to which polar head groups are attached. The discovery of CarS enabled reconstitution of the entire archaeal lipid biosynthesis pathway in vitro, starting from simple isoprenoid building blocks and using a set of five purified enzymes. The cell free synthetic strategy for archaeal lipids we describe opens opportunity for studies of archaeal lipid biochemistry. Additionally, insights into archaeal lipid biosynthesis reported here allow addressing the evolutionary hypothesis of the lipid divide between Archaea and Bacteria.