Acetic acid (S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxy-3-oxo-1,3-dihydro-isobenzofuran-1-ylmethyl ester | 721448-82-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: Acetic acid (S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxy-3-oxo-1,3-dihydro-isobenzofuran-1-ylmethyl ester
• CAS: 721448-82-4
• 化学式: C₁₈H₂₆O₆Si
• 分子量: 366.486
• InChiKey: MUOKBXDEOHDORQ-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.34
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  82.06
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxy-3-oxo-1,3-dihydro-isobenzofuran-1-ylmethyl ester 在 氟化氢吡啶 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 吡啶 、 二氯甲烷 为溶剂， 生成 Acetic acid (R)-4-[10-((R)-1-acetoxymethyl-1-hydroxymethyl-3-oxo-1,3-dihydro-isobenzofuran-4-yloxy)-decyloxy]-1-hydroxymethyl-3-oxo-1,3-dihydro-isobenzofuran-1-ylmethyl ester
  参考文献：
  名称：

  Evaluation of series of isobenzofuranone dimers as PKCα ligands: implication for the distance between the two ligand binding sites

  摘要：

  Protein kinase C (PKC) is a family of enzymes, which play important roles in intracellular signal transduction. To examine the distance between the two ligand binding sites (C1A and C1B) of PKC, we designed and synthesized two series of isobenzofuranone dimers. Peak binding activities were observed for the C3-acyl chain dimers having a C-10-C-12 linker and for the C7 dimers having a C-14-C-16. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.02.098
• 作为产物：
  描述：

  Acetic acid (S)-4-benzyloxy-1-(tert-butyl-dimethyl-silanyloxymethyl)-3-oxo-1,3-dihydro-isobenzofuran-1-ylmethyl ester 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 以97%的产率得到Acetic acid (S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxy-3-oxo-1,3-dihydro-isobenzofuran-1-ylmethyl ester
  参考文献：
  名称：

  Design, synthesis, and structure–activity relationship of new isobenzofuranone ligands of protein kinase C

  摘要：

  Protein kinase C (PKC) is a family of enzymes, which play important roles in intracellular signal transduction. We have designed novel PKC ligands having an isobenzofuranone template, based on the proposed interaction of DAG (1,2-diacyl-sn-glycerol) with the PKCdelta C1B ligand-binding domain. Several isobenzofuranone derivatives were synthesized and their PKCalpha binding activities were evaluated. The pivaloyl derivative 1f was found to be a strong PKCalpha ligand, and the structure-activity relationship is well explained by our proposed binding model. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.02.097