4-<(benzyloxy)methyl>-4-<(tert-butyldimethylsiloxy)methyl>tetrahydro-2-furanone | 130838-67-4

• 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-<(benzyloxy)methyl>-4-<(tert-butyldimethylsiloxy)methyl>tetrahydro-2-furanone
• 英文别名: 4-[(Benzyloxy)methyl]-4-[(tert-butyldimethylsiloxy)methyl]-tetrahydro-2-furanone；4-[[Tert-butyl(dimethyl)silyl]oxymethyl]-4-(phenylmethoxymethyl)oxolan-2-one
• CAS: 130838-67-4
• 化学式: C₁₉H₃₀O₄Si
• 分子量: 350.53
• InChiKey: PVPMAUMDUQKLDV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.16
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 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-<(benzyloxy)methyl>-4-<(tert-butyldimethylsiloxy)methyl>tetrahydro-2-furanone 在 diisobutylaluminum hydride 作用下， 以 二氯甲烷 为溶剂， 生成 4-Benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-ol
  参考文献：
  名称：

  经由（双三氟乙酰氧基碘）苯介导的1,3-二硫杂环丁烷和乙基烯醇醚的环化反应合成6-羟基-5,5-二烷基取代的环己烯酮

  摘要：

  由（双三氟乙酰氧基碘）苯介导的在同一分子中的1,3-二噻吩和乙基烯醇醚的新型分子内醇醛反应用于合成6-羟基-5,5-二烷基取代的环己烯酮。

  DOI：

  10.1039/c39900001033
• 作为产物：
  描述：

  4-Benzyloxymethyl-4-vinyl-dihydro-furan-2-one 在 咪唑 、 sodium tetrahydroborate 、 sodium periodate 、 四氧化锇 、 水 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 、 丙酮 、 叔丁醇 为溶剂， 反应 34.5h， 生成 4-<(benzyloxy)methyl>-4-<(tert-butyldimethylsiloxy)methyl>tetrahydro-2-furanone
  参考文献：
  名称：

  Conformationally Constrained Analogues of Diacylglycerol. 10. Ultrapotent Protein Kinase C Ligands Based on a Racemic 5-Disubstituted Tetrahydro-2-furanone Template

  摘要：

  5,5-Bis(hydroxymethyl)tetrahydro-2-furanone and its isomer 4,4-bis(hydroxymethyl)tetrahydro-2-furanone were investigated as possible templates for the construction of conformationally constrained analogues of the biologically important second messenger, diacylglycerol (DAG). The former lactone contains embedded within its structure an exact glycerol moiety, while in the latter the ring oxygen has been transposed to the other side of the carbonyl group. Al target compounds were synthesized as racemates from 1,3-dihydroxy-2-propanone. The 5,5-bis(hydroxymethyl)tetrahydro-2-furanone proved to be the better template for the construction of DAG surrogates that were demonstrated to have high binding affinities for the biological target, protein kinase C (PK-C). The simplest target compounds derived from this template (3e and 3f) have one of the hydroxyl moieties functionalized either as a myristate or as an oleate ester. The simplest target compound (9e) derived from the ineffective 4,4-bis(hydroxymethyl)tetrahydro-2-furanone template was investigated only with a myristoyl acyl chain. Reducing the long acyl chain to an acetyl moiety and attaching a compensating lipophilic chain to the lactone ring as an alpha-alkylidene moiety produced compounds 10e and 10f(Z-isomers) and 11e and 11f(E-isomers), which were constructed on the more effective 5,5-bis(hydroxymethyl)tetrahydro-2-furanone template. Targets 14c (Z-isomer) and 15c (E-isomer) were derived, in turn, from 4,4-bis(hydroxymethyl)tetrahydro-2-furan. The affinities of these ligands for PK-C were assessed in terms of their ability to displace bound [H-3-20]phorbol 12,13-dibutyrate (PDBU) from the single isozyme PK-C alpha. The biological data support the hypothesis that the increase in binding affinity for PK-C shown by some of these constrained DAG mimetics appears to be entropic in nature. Two of the designed ligands (10e and 10f) showed the highest affinities (34 and 24 nM, respectively) reported so far for a DAG analogue. Assuming that the interaction between these racemic compounds and PK-C is stereospecific, the potency of the active enantiomer is anticipated to double.

  DOI：

  10.1021/jm950276v

文献信息

• Conformationally constrained diacylglycerol analogues
  申请人：The United States of America as represented by the Department of Health

  公开号：US05874464A1

  公开（公告）日：1999-02-23

  Conformationally constrained diacylglycerol analogues, pharmaceutical compositions comprising such analogues, and methods of using such analogues as agonists and antagonists of protein kinase C.

  构象受限的二酰基甘油类似物，包含这种类似物的药物组合物，以及使用这种类似物作为蛋白激酶C的激动剂和拮抗剂的方法。
• UENISHI, JUNICHI;KAWACHI, YASUHIRO;WAKABAYASHI, SHOJI, J. CHEM. SOC. CHEM. COMMUN.,(1990) N5, C. 1033-1034
  作者：UENISHI, JUNICHI、KAWACHI, YASUHIRO、WAKABAYASHI, SHOJI

  DOI：——

  日期：——