[(1R)-4-hydroxy-3-oxo-1-(phenylmethoxymethyl)-2-benzofuran-1-yl]methyl 2-tert-butyl-3,3-dimethylbutanoate | 1170721-85-3

• 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: [(1R)-4-hydroxy-3-oxo-1-(phenylmethoxymethyl)-2-benzofuran-1-yl]methyl 2-tert-butyl-3,3-dimethylbutanoate
• CAS: 1170721-85-3
• 化学式: C₂₇H₃₄O₆
• 分子量: 454.563
• InChiKey: HZKUYVZYRRTBQL-HHHXNRCGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(1R)-4-hydroxy-3-oxo-1-(phenylmethoxymethyl)-2-benzofuran-1-yl]methyl 2-tert-butyl-3,3-dimethylbutanoate 在 咪唑 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 20 % Pd(OH)2/C 、 氢气 、 三乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 生成 C₅₁H₈₆O₁₁Si
  参考文献：
  名称：

  Design and synthesis of protein kinase Cα activators based on ‘out of pocket’ interactions

  摘要：

  Novel types of PKC alpha activators based on isobenzofuranone bearing a myo-inositol moiety were designed and synthesized. The derivatives with bulky substituents on the myo-inositol moiety significantly activated PKC alpha, but their binding sites were not the same as that of phorbol ester. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.04.108
• 作为产物：
  描述：

  (R)-(1-((benzyloxy)methyl)-4-(methoxymethoxy)-3-oxo-1,3-dihydroisobenzofuran-1-yl)methyl 2-(tert-butyl)-3,3-dimethylbutanoate 在 三甲基溴硅烷 作用下， 以 二氯甲烷 为溶剂， 以95%的产率得到[(1R)-4-hydroxy-3-oxo-1-(phenylmethoxymethyl)-2-benzofuran-1-yl]methyl 2-tert-butyl-3,3-dimethylbutanoate
  参考文献：
  名称：

  Asymmetric synthesis of isobenzofuranone derivatives and their unique character as protein kinase Cα (PKCα) activators

  摘要：

  Efficient enantio-selective synthesis of conformationally constrained diacylglycerol analogues, 7-substituted isobenzofuranone derivatives, originally developed by us as PKC alpha ligands, was achieved by asymmetric dihydroxylation and gamma-lactone formation via ortho-lithiation and carboxylation. A series of derivatives having straight and/or branched side chains were synthesized and evaluated, and low-nanomolar-concentration affinity ligands and highly potent PKC alpha activators were found among them. These potent ligands induced phenotypic change of K562 cells, which is characteristic of PKC activators. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.03.069