1-(4-((dimethoxyphosphoryloxy)methyl)-2-oxodihydrofuran-3(2H)-ylidene)ethyl acetate | 1309477-54-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物
• 英文名称: 1-(4-((dimethoxyphosphoryloxy)methyl)-2-oxodihydrofuran-3(2H)-ylidene)ethyl acetate
• CAS: 1309477-54-0
• 化学式: C₁₁H₁₇O₈P
• 分子量: 308.225
• InChiKey: DUELJGDPKOOQKU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.41
• 重原子数：
  20.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  97.36
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  1-(4-((dimethoxyphosphoryloxy)methyl)-2-oxodihydrofuran-3(2H)-ylidene)ethyl acetate 在 4-二甲氨基吡啶 、 sodium iodide 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  The First Total Synthesis of (±)-Cyclophostin and (±)-Cyclipostin P: Inhibitors of the Serine Hydrolases Acetyl Cholinesterase and Hormone Sensitive Lipase

  摘要：

  Cyclophostin, a structurally unique and potent naturally occurring acetyl cholinesterase (AChE) Inhibitor, and its unnatural diastereomer were prepared in 6 steps and 15% overall yield from hydroxymethyl butyrolactone. The unnatural diastereomer of cyclophostin was converted into cyclipostin P, a potent naturally occurring hormone sensitive lipase (HSL) inhibitor, using a one pot dealkylation-alkylation process. The inhibition [IC50] of human AChE by cyclophostin and its diastereomer are reported, as well as constituent binding (K-1) and reactivity (k(2)) constants.

  DOI：

  10.1021/ol200991x
• 作为产物：
  描述：

  3-羟基甲基-4-丁内酯 在 溴 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.37h， 生成 1-(4-((dimethoxyphosphoryloxy)methyl)-2-oxodihydrofuran-3(2H)-ylidene)ethyl acetate
  参考文献：
  名称：

  The First Total Synthesis of (±)-Cyclophostin and (±)-Cyclipostin P: Inhibitors of the Serine Hydrolases Acetyl Cholinesterase and Hormone Sensitive Lipase

  摘要：

  Cyclophostin, a structurally unique and potent naturally occurring acetyl cholinesterase (AChE) Inhibitor, and its unnatural diastereomer were prepared in 6 steps and 15% overall yield from hydroxymethyl butyrolactone. The unnatural diastereomer of cyclophostin was converted into cyclipostin P, a potent naturally occurring hormone sensitive lipase (HSL) inhibitor, using a one pot dealkylation-alkylation process. The inhibition [IC50] of human AChE by cyclophostin and its diastereomer are reported, as well as constituent binding (K-1) and reactivity (k(2)) constants.

  DOI：

  10.1021/ol200991x