(3R,8aR)-3-甲氧基-5-甲基-8,8A-二氢-1H,6H-呋喃并[3,4-e][1,3,2]二氧杂磷杂卓-6-酮3-氧化物 | 144773-26-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 中文名称: (3R,8aR)-3-甲氧基-5-甲基-8,8A-二氢-1H,6H-呋喃并[3,4-e][1,3,2]二氧杂磷杂卓-6-酮3-氧化物
• 英文名称: (±)-cyclophostin
• 英文别名: (3RS,8aRS)-3-methoxy-5-methyl-8,8a-dihydrofuro[3,4-e][1,3,2]dioxaphosphepin-6(1H)-one 3-oxide；(+/-)-cyclophostin；Cyclophostin；(3R,8aR)-3-methoxy-5-methyl-3-oxo-8,8a-dihydro-1H-furo[3,4-e][1,3,2]dioxaphosphepin-6-one
• CAS: 144773-26-2
• 化学式: C₈H₁₁O₆P
• 分子量: 234.145
• InChiKey: OMPQJMDGDAAXPE-NPMWZIQKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-羟基甲基-4-丁内酯 在 吡啶 、 4-二甲氨基吡啶 、 溴 、 对甲苯磺酰氯 、 sodium iodide 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 2.37h， 生成 (3R,8aR)-3-甲氧基-5-甲基-8,8A-二氢-1H,6H-呋喃并[3,4-e][1,3,2]二氧杂磷杂卓-6-酮3-氧化物
  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.