2,2-Dimethyl-propionic acid (R)-1-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxy-3-oxo-1,3-dihydro-isobenzofuran-1-ylmethyl ester | 721449-14-5

• 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: 2,2-Dimethyl-propionic acid (R)-1-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxy-3-oxo-1,3-dihydro-isobenzofuran-1-ylmethyl ester
• CAS: 721449-14-5
• 化学式: C₂₁H₃₂O₆Si
• 分子量: 408.567
• InChiKey: BAVSVPADMALBAD-OAQYLSRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.37
• 重原子数：
  28.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 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：

  2,2-Dimethyl-propionic acid (R)-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 2,2-Dimethyl-propionic acid (S)-4-dodecyloxy-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：

  2,2-Dimethyl-propionic acid (R)-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， 生成 2,2-Dimethyl-propionic acid (R)-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