2,2-dimethyl-5-(2'-diethylphosphono)ethyl-1,3-dioxane | 182691-01-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物
• 英文名称: 2,2-dimethyl-5-(2'-diethylphosphono)ethyl-1,3-dioxane
• CAS: 182691-01-6
• 化学式: C₁₂H₂₅O₅P
• 分子量: 280.301
• InChiKey: JVGXCFSBTRBJSW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.04
• 重原子数：
  18.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  53.99
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2,2-dimethyl-5-(2'-diethylphosphono)ethyl-1,3-dioxane 在 palladium on activated charcoal jones reagent 、 二苯基膦叠氮化物 、 氢气 、 对甲苯磺酸 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 丙酮 为溶剂， 20.0~25.0 ℃ 、101.33 kPa 条件下， 反应 35.5h， 生成 S(+)-2-amino-4-diethoxyphosphonobutanoic acid
  参考文献：
  名称：

  Lipase-catalyzed enantioselective acylation of prochiral 2-(ω-phosphono)alkyl-1,3-propanediols: Application to the enantioselective synthesis of ω-phosphono-α-amino acids

  摘要：

  Lipase PS catalyzed acetylation of prochiral 2-(omega-phosphono)alkyl-1,3-propanediols 1a-c was found to proceed with high enantioselectivity. The applications of phosphonic chirons 2a-c thus obtained were illustrated by the stereocontrolled synthesis of omega-phosphono-alpha-amino acids such as L-AP-3, L-AP-4, and N-Boc-L-F(2)Pab(OEt)(2)-OH. Copyright (C) 1996 Published by Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00354-0
• 作为产物：
  描述：

  (2,2-二甲基-1,3-二氧六环-5-基)甲醇 在 吡啶 、 正丁基锂 作用下， 以 二氯甲烷 为溶剂， 反应 1.83h， 生成 2,2-dimethyl-5-(2'-diethylphosphono)ethyl-1,3-dioxane
  参考文献：
  名称：

  Lipase-catalyzed enantioselective acylation of prochiral 2-(ω-phosphono)alkyl-1,3-propanediols: Application to the enantioselective synthesis of ω-phosphono-α-amino acids

  摘要：

  Lipase PS catalyzed acetylation of prochiral 2-(omega-phosphono)alkyl-1,3-propanediols 1a-c was found to proceed with high enantioselectivity. The applications of phosphonic chirons 2a-c thus obtained were illustrated by the stereocontrolled synthesis of omega-phosphono-alpha-amino acids such as L-AP-3, L-AP-4, and N-Boc-L-F(2)Pab(OEt)(2)-OH. Copyright (C) 1996 Published by Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00354-0

文献信息

• A new class of acyclic phosphonate nucleotide analogs: Phosphonate isosteres of acyclovir and ganciclovir monophosphates as antiviral agents
  作者：Choung Un Kim、Peter F. Misco、Bing Yu Luh、Michael J. M. Hitchcock、Ismail Ghazzouli、John C. Martin

  DOI：10.1021/jm00111a052

  日期：1991.7

  Novel phosphonate isosteres of acyclovir (ACV) and ganciclovir (DHPG) monophosphates (20 and 32) were found to be potent and selective antiherpesvirus agents. In the series of phosphonate analogues of ACV monophosphate, only the guanine analogue 20 exhibited activity against herpesviruses, similar to the structure-activity relationship observed for base modification of ACV analogues. The phosphonate isostere of ACV monophosphate (20) was more effective than ACV in the HSV-1 infected mouse model. The 3'-carba analogues of 9-[3-hydroxy-2-(phosphonomethoxy)propyl]purines/pyrimidines (adenine, HPMPA; guanine, HPMPG; cytosine, HPMPC) are devoid of antiherpesvirus activity. This result confirms that the beta-oxygen atom of the phosphonomethyl ether functionality in HPMP-purines/pyrimidines plays a critical role for activity against herpesviruses.