4-(4-Methoxy-benzyloxy-methyl)-tetrahydrofuran-2-one | 131072-60-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(4-Methoxy-benzyloxy-methyl)-tetrahydrofuran-2-one
• 英文别名: 4-((4-methoxybenzyloxy)methyl)dihydrofuran-2(3H)-one；4-[(4-Methoxyphenyl)methoxymethyl]oxolan-2-one
• CAS: 131072-60-1
• 化学式: C₁₃H₁₆O₄
• 分子量: 236.268
• InChiKey: ODFRZUVLBNPAAI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(4-Methoxy-benzyloxy-methyl)-tetrahydrofuran-2-one 在 N,N-二异丙基乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.08h， 生成 (E)-1-(4-(4-methoxybenzyloxymethyl)-2-oxodihydrofuran-3(2H)-ylidene)ethyl dimethyl 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
• 作为产物：
  描述：

  甲酸基丁二酸二乙酯 在 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 23.5h， 生成 4-(4-Methoxy-benzyloxy-methyl)-tetrahydrofuran-2-one
  参考文献：
  名称：

  Five membered ring formation of 2-hydroxyalkyl malonate and acetoacetate derivatives the problem of O-versus C-alkylation

  摘要：

  DOI：

  10.1016/s0040-4020(01)87922-9

文献信息

• First total synthesis of a new sesquiterpenoid natural product, (±)-3-(2,4-dihydroxybenzoyl)-4,5-dimethyl-5-(4,8-dimethyl-3(E),7(E)-nonadien-1-yl)tetrahydro-2-furanone
  作者：Hidemi Yoda、Kazuhide Maruyama、Kunihiko Takabe

  DOI：10.1016/s0040-4039(03)00146-1

  日期：2003.2

  An efficient and stereodefined process is described for the first preparation of a new prenyl-benzoylfuranone type sesquiterpenoid, (±)-3-(2,4-dihydroxybenzoyl)-4,5-dimethyl-5-(4,8-dimethyl-3(E),7(E)-nonadien-1-yl)tetrahydro-2-furanone. The synthetic strategy is based on nucleophilic addition of organometallic reagents to the functionalized ketoamides elaborated from dihydroxyacetone dimer for the

  描述了一种高效且立体明确的方法，用于首次制备新的异戊二烯-苯甲酰基呋喃酮型倍半萜，（±）-3-（2,4-二羟基苯甲酰基）-4,5-二甲基-5-（4,8-二甲基-3） （E），7（E）-壬二烯-1-基）四氢-2-呋喃酮。合成策略基于将有机金属试剂亲核加成到由二羟基丙酮二聚体修饰的官能化酮酰胺上，以立体选择性地构建目标化合物中关键的季碳中心。
• 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.
• Five membered ring formation of 2-hydroxyalkyl malonate and acetoacetate derivatives the problem of O-versus C-alkylation
  作者：Elisabeth Adams、Monika Hiegemann、Helmut Duddeck、Peter Welzel

  DOI：10.1016/s0040-4020(01)87922-9

  日期：1990.1