5-[(S)-4-tert-butyldimethylsilyloxy-3-methylbutoxy]-7-methoxy-4,6-dimethyl-1(3H)-isobenzofuranone | 1065231-13-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异香豆素
• 英文名称: 5-[(S)-4-tert-butyldimethylsilyloxy-3-methylbutoxy]-7-methoxy-4,6-dimethyl-1(3H)-isobenzofuranone
• 英文别名: 5-[(3S)-4-[tert-butyl(dimethyl)silyl]oxy-3-methylbutoxy]-7-methoxy-4,6-dimethyl-3H-2-benzofuran-1-one
• CAS: 1065231-13-1
• 化学式: C₂₂H₃₆O₅Si
• 分子量: 408.61
• InChiKey: ZGDBMQJREAFDJQ-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.41
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-[(S)-4-tert-butyldimethylsilyloxy-3-methylbutoxy]-7-methoxy-4,6-dimethyl-1(3H)-isobenzofuranone 在 magnesium iodide 、 盐酸 作用下， 以 乙醚 、 甲苯 、 甲醇 为溶剂， 反应 3.5h， 以88%的产率得到5-[(S)-4-hydroxy-3-methylbutoxy]-7-hydroxy-4,6-dimethyl-1(3H)-isobenzofuranone
  参考文献：
  名称：

  Synthesis of novel antifungal phthalides produced by a wheat rhizosphere fungus

  摘要：

  Two antifungal phthalides produced by a wheat rhizosphere fungus have been synthesized using the Alder-Rickert reaction to construct their common isobenzofuranone core structure. The absolute configuration of one of the two phthalides has been determined to be S by synthesizing its (S)- and (R)-enantiomer and comparing their optical rotations with that of the natural product. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.07.023
• 作为产物：
  描述：

  5-hydroxy-7-methoxy-4,5-dimethyl-1(3H)-isobenzofuranone 、 (3S)-1-<(tert-butyldimethylsilyl)oxy>-4-iodo-3-methylbutane 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 以90%的产率得到5-[(S)-4-tert-butyldimethylsilyloxy-3-methylbutoxy]-7-methoxy-4,6-dimethyl-1(3H)-isobenzofuranone
  参考文献：
  名称：

  Synthesis of novel antifungal phthalides produced by a wheat rhizosphere fungus

  摘要：

  Two antifungal phthalides produced by a wheat rhizosphere fungus have been synthesized using the Alder-Rickert reaction to construct their common isobenzofuranone core structure. The absolute configuration of one of the two phthalides has been determined to be S by synthesizing its (S)- and (R)-enantiomer and comparing their optical rotations with that of the natural product. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.07.023