(E)-1-(4-(hydroxymethyl)-2-oxodihydrofuran-3(2H)-ylidene)ethyl methyl hydrogen phosphate | 1309477-53-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 英文名称: (E)-1-(4-(hydroxymethyl)-2-oxodihydrofuran-3(2H)-ylidene)ethyl methyl hydrogen phosphate
• 英文别名: [(1E)-1-[4-(hydroxymethyl)-2-oxooxolan-3-ylidene]ethyl] methyl hydrogen phosphate
• CAS: 1309477-53-9
• 化学式: C₈H₁₃O₇P
• 分子量: 252.161
• InChiKey: ZSYNSYDXMZCIGR-FNORWQNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (E)-1-(4-(hydroxymethyl)-2-oxodihydrofuran-3(2H)-ylidene)ethyl methyl hydrogen phosphate 在 4-二甲氨基吡啶 、 四丁基碘化铵 、 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 (3RS,8aSR)-3-hexadecyloxy-5-methyl-8,8a-dihydrofuro[3,4-e][1,3,2]dioxaphosphepin-6(1H)-one 3-oxide 、 (3RS,8aRS)-3-hexadecyloxy-5-methyl-8,8a-dihydrofuro[3,4-e][1,3,2]dioxaphosphepin-6(1H)-one 3-oxide
  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 甲醇 、 copper(II) bis(trifluoromethanesulfonate) 、 N,N-二异丙基乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 sodium iodide 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 、 甲苯 为溶剂， 反应 4.08h， 生成 (E)-1-(4-(hydroxymethyl)-2-oxodihydrofuran-3(2H)-ylidene)ethyl methyl hydrogen phosphate
  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

文献信息

• The First Total Synthesis of (±)-Cyclophostin and (±)-Cyclipostin P: Inhibitors of the Serine Hydrolases Acetyl Cholinesterase and Hormone Sensitive Lipase
  作者：Raj K. Malla、Saibal Bandyopadhyay、Christopher D. Spilling、Supratik Dutta、Cynthia M. Dupureur

  DOI：10.1021/ol200991x

  日期：2011.6.17

  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.