2-[(E)-benzylidene]-3-[(tert-butyl)dimethylsilyloxy]propanal | 518358-00-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醛
• 英文名称: 2-[(E)-benzylidene]-3-[(tert-butyl)dimethylsilyloxy]propanal
• CAS: 518358-00-4
• 化学式: C₁₆H₂₄O₂Si
• 分子量: 276.451
• InChiKey: IWBYQFHKDNENGZ-PTNGSMBKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.29
• 重原子数：
  19.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  丙烯酸甲酯（MA） 、 2-[(E)-benzylidene]-3-[(tert-butyl)dimethylsilyloxy]propanal 在 三乙烯二胺 、 三乙醇胺 、 lanthanum(lll) triflate 作用下， 以 乙腈 为溶剂， 反应 336.0h， 以29%的产率得到methyl (E)-4-{[(tert-butyl)dimethylsilyloxy]methyl}-3-hydroxy-2-methylene-5-phenylpent-4-enoate
  参考文献：
  名称：

  Synthesis and MMP-Inhibitory Activity of Gelastatin Analogues

  摘要：

  Gelastatin A and B, isolated from culture broth of Westerdykella mititispora F 50733, have been reported to exhibit MMP-inhibitory activities at a sub-micromolar level. In an effort to exploit this lead, we synthesized gelastatin analogues in which the conjugated triene unit of natural gelastatins was replaced by the benzylidene group. The (Z)-isomeric synthetic benzylidene-gelastatin exhibited MMP-inhibitory activities comparable to those reported for the natural products. Therefore, this compound appears to be a viable lead in searching for therapeutically useful MMP inhibitors.

  DOI：

  10.1002/1522-2675(200211)85:11<3994::aid-hlca3994>3.0.co;2-2
• 作为产物：
  描述：

  亚苄基丙二酸二甲酯 在 Celite 、 sodium hydride 、 二异丁基氢化铝 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 11.0h， 生成 2-[(E)-benzylidene]-3-[(tert-butyl)dimethylsilyloxy]propanal
  参考文献：
  名称：

  Synthesis and MMP-Inhibitory Activity of Gelastatin Analogues

  摘要：

  Gelastatin A and B, isolated from culture broth of Westerdykella mititispora F 50733, have been reported to exhibit MMP-inhibitory activities at a sub-micromolar level. In an effort to exploit this lead, we synthesized gelastatin analogues in which the conjugated triene unit of natural gelastatins was replaced by the benzylidene group. The (Z)-isomeric synthetic benzylidene-gelastatin exhibited MMP-inhibitory activities comparable to those reported for the natural products. Therefore, this compound appears to be a viable lead in searching for therapeutically useful MMP inhibitors.

  DOI：

  10.1002/1522-2675(200211)85:11<3994::aid-hlca3994>3.0.co;2-2