6a-deuterio-4-methylidene-3,3a-dihydro-2H-furo[2,3-b]furan | 1443118-31-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃类
• 英文名称: 6a-deuterio-4-methylidene-3,3a-dihydro-2H-furo[2,3-b]furan
• CAS: 1443118-31-7
• 化学式: C₇H₁₀O₂
• 分子量: 127.147
• InChiKey: ITEHUTGZBAGJOG-WHRKIXHSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6a-deuterio-4-methylidene-3,3a-dihydro-2H-furo[2,3-b]furan 在 4-二甲氨基吡啶 、 sodium hypophosphate 、 deutero lithium aluminiumhydride 、 sodium carbonate 、 potassium carbonate 、 臭氧 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 aq. phosphate buffer 、 二氯甲烷 为溶剂， 反应 38.83h， 生成 (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol-d2
  参考文献：
  名称：

  Synthesis and pharmacokinetic profile of highly deuterated brecanavir analogs

  摘要：

  Several highly deuterated analogs of the HIV-1 protease inhibitor brecanavir have been prepared to study the effect of deuterium upon metabolic stability. The sites for deuterium incorporation were initially chosen to maximize the potential for a kinetic isotope effect; locations where C-H bond breaking is the rate limiting step. The analogs have been profiled in both in vitro and in vivo pharmacokinetic studies and the result will be described herein. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.02.001
• 作为产物：
  描述：

  3-Bromo-2-deuterio-2-prop-2-ynoxyoxolane 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以2.17 g的产率得到6a-deuterio-4-methylidene-3,3a-dihydro-2H-furo[2,3-b]furan
  参考文献：
  名称：

  Synthesis and pharmacokinetic profile of highly deuterated brecanavir analogs

  摘要：

  Several highly deuterated analogs of the HIV-1 protease inhibitor brecanavir have been prepared to study the effect of deuterium upon metabolic stability. The sites for deuterium incorporation were initially chosen to maximize the potential for a kinetic isotope effect; locations where C-H bond breaking is the rate limiting step. The analogs have been profiled in both in vitro and in vivo pharmacokinetic studies and the result will be described herein. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.02.001

文献信息

• Synthesis and pharmacokinetic profile of highly deuterated brecanavir analogs
  作者：Emile J. Velthuisen、Todd M. Baughman、Brian A. Johns、David P. Temelkoff、Jason G. Weatherhead

  DOI：10.1016/j.ejmech.2013.02.001

  日期：2013.5

  Several highly deuterated analogs of the HIV-1 protease inhibitor brecanavir have been prepared to study the effect of deuterium upon metabolic stability. The sites for deuterium incorporation were initially chosen to maximize the potential for a kinetic isotope effect; locations where C-H bond breaking is the rate limiting step. The analogs have been profiled in both in vitro and in vivo pharmacokinetic studies and the result will be described herein. (C) 2013 Elsevier Masson SAS. All rights reserved.