(2R)-3,3-difluoro-2-[(1-tert-butyl-1,1-dimethylsilyl)oxy]-1-propanol | 474329-41-4

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (2R)-3,3-difluoro-2-[(1-tert-butyl-1,1-dimethylsilyl)oxy]-1-propanol
• 英文别名: (2R)-3,3-difluoro-2-{[1-(t-butyl)-1,1-dimethylsilyl]oxy}-1-propanol；(2R)-2-[tert-butyl(dimethyl)silyl]oxy-3,3-difluoropropan-1-ol
• CAS: 474329-41-4
• 化学式: C₉H₂₀F₂O₂Si
• 分子量: 226.339
• InChiKey: DNEIOPRSDIVWSH-SSDOTTSWSA-N

物化性质

• 沸点：
  233.9±40.0 °C(Predicted)
• 密度：
  0.990±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.63
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R)-3,3-difluoro-2-[(1-tert-butyl-1,1-dimethylsilyl)oxy]-1-propanol 在 2,6-二甲基吡啶 、 六甲基磷酰三胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 methyl (4R)-4-[tert-butyl(dimethyl)silyl]oxy-5,5-difluoro-2-phenylsulfanylpentanoate
  参考文献：
  名称：

  Design and synthesis of C35-fluorinated solamins and their growth inhibitory activities against human cancer cell lines

  摘要：

  The convergent synthesis of C35-fluorinated analogues of solamin, a mono-THF Annonaceous acetogenin, has been achieved by the Sonogashira coupling of the THF ring fragment and the fluorinated gamma-lactone fragment. It was revealed that the number of fluorine atoms on the gamma-lactone moiety affects the growth inhibitory activities against human cancer cell lines. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.08.011
• 作为产物：
  描述：

  (2R)-3,3-difluoro-1,2-bis[(1-tert-butyl-1,1-dimethylsilyl)oxy]propane 在 吡啶 、 氟化氢吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 以73%的产率得到(2R)-3,3-difluoro-2-[(1-tert-butyl-1,1-dimethylsilyl)oxy]-1-propanol
  参考文献：
  名称：

  Concise Synthesis of Acyl Migration-Blocked 1,1-Difluorinated Analogues of Lysophosphatidic Acid

  摘要：

  Lysophosphatidic acid (LPA, 1- or 2-acyl-sn-glycerol 3-phosphate) is an important phospholipid mediator produced by activated platelets and by ovarian cancer cells. Efforts to understand LPA signaling through G-protein-coupled receptors are hampered by the facile acyl migration that results in equilibration to a mixture of the 1- or 2-acyl species under physiological conditions. We describe a new and efficient route to enantiomerically homogeneous lysophospholipid analogues from D-mannitol 1,2:5,6-bis-ace-tonide to give two 1,1-difluorodeoxy analogues of (2R)-acyl-sn-glycerol 3-phosphate. These compounds are migration-blocked analogues of the labile sn-2 LPA species. The F-19 NMR of diastereotopic fluorines, of the difluoromethyl group shows an unexpected solvent dependence.

  DOI：

  10.1021/jo0203037

文献信息

• [EN] ANALOGS OF LYSOPHOSPHATIDIC ACID AND METHODS OF MAKING AND USING THEREOF<br/>[FR] ANALOGUES D'ACIDE LYSOPHOSPHATIDIQUE ET PROCEDES DE LEUR FABRICATION ET DE LEUR UTILISATION
  申请人：UNIV UTAH RES FOUND

  公开号：WO2004092188A3

  公开（公告）日：2005-04-28
• Design and synthesis of C35-fluorinated solamins and their growth inhibitory activities against human cancer cell lines
  作者：Naoto Kojima、Yuki Suga、Hiromi Hayashi、Takao Yamori、Takehiko Yoshimitsu、Tetsuaki Tanaka

  DOI：10.1016/j.bmcl.2011.08.011

  日期：2011.10

  The convergent synthesis of C35-fluorinated analogues of solamin, a mono-THF Annonaceous acetogenin, has been achieved by the Sonogashira coupling of the THF ring fragment and the fluorinated gamma-lactone fragment. It was revealed that the number of fluorine atoms on the gamma-lactone moiety affects the growth inhibitory activities against human cancer cell lines. (C) 2011 Elsevier Ltd. All rights reserved.
• Concise Synthesis of Acyl Migration-Blocked 1,1-Difluorinated Analogues of Lysophosphatidic Acid
  作者：Yong Xu、Glenn D. Prestwich

  DOI：10.1021/jo0203037

  日期：2002.10.1

  Lysophosphatidic acid (LPA, 1- or 2-acyl-sn-glycerol 3-phosphate) is an important phospholipid mediator produced by activated platelets and by ovarian cancer cells. Efforts to understand LPA signaling through G-protein-coupled receptors are hampered by the facile acyl migration that results in equilibration to a mixture of the 1- or 2-acyl species under physiological conditions. We describe a new and efficient route to enantiomerically homogeneous lysophospholipid analogues from D-mannitol 1,2:5,6-bis-ace-tonide to give two 1,1-difluorodeoxy analogues of (2R)-acyl-sn-glycerol 3-phosphate. These compounds are migration-blocked analogues of the labile sn-2 LPA species. The F-19 NMR of diastereotopic fluorines, of the difluoromethyl group shows an unexpected solvent dependence.