Acetic acid (S)-4-benzyloxy-1-(tert-butyl-dimethyl-silanyloxymethyl)-3-oxo-1,3-dihydro-isobenzofuran-1-ylmethyl ester | 721448-96-0

• 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)-4-benzyloxy-1-(tert-butyl-dimethyl-silanyloxymethyl)-3-oxo-1,3-dihydro-isobenzofuran-1-ylmethyl ester
• 英文别名: [(1S)-1-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-oxo-4-phenylmethoxy-2-benzofuran-1-yl]methyl acetate
• CAS: 721448-96-0
• 化学式: C₂₅H₃₂O₆Si
• 分子量: 456.611
• InChiKey: JYLJHDPXZCWSLX-VWLOTQADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.22
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Acetic acid (S)-4-benzyloxy-1-(tert-butyl-dimethyl-silanyloxymethyl)-3-oxo-1,3-dihydro-isobenzofuran-1-ylmethyl ester 在 氟化氢吡啶 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 113.0h， 以98%的产率得到Acetic acid (R)-4-benzyloxy-1-hydroxymethyl-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
• 作为产物：
  描述：

  N,N-二乙基水杨酰胺 在 咪唑 、 4-二甲氨基吡啶 、 四甲基乙二胺 、 仲丁基锂 、 silica gel 、 potassium carbonate 、 氟化氢吡啶 、 三乙胺 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 181.5h， 生成 Acetic acid (S)-4-benzyloxy-1-(tert-butyl-dimethyl-silanyloxymethyl)-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