2-(Hydroxymethyl)-4-<(tert-butyldimethylsilyl)oxy>butanenitrile | 152754-82-0

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 2-(Hydroxymethyl)-4-<(tert-butyldimethylsilyl)oxy>butanenitrile
• CAS: 152754-82-0
• 化学式: C₁₁H₂₃NO₂Si
• 分子量: 229.395
• InChiKey: IYOPEXGYQJZJPW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.53
• 重原子数：
  15.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  53.25
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-(Hydroxymethyl)-4-<(tert-butyldimethylsilyl)oxy>butanenitrile 在 sodium tetrahydroborate 、 N-氯代丁二酰亚胺 、 lithium aluminium tetrahydride 、 二甲基硫 、 sodium sulfate 作用下， 以 甲醇 、 乙醚 、 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 80.08h， 生成 7-<1-<2-<(tert-Butyldimethylsilyl)oxy>ethyl>>-N'''-carbobenzoxy-N,N',N''-tricarbo-tert-butoxythermospermine
  参考文献：
  名称：

  Synthesis of philanthotoxin analogs with a branched polyamine moiety

  摘要：

  Philanthotoxin (PhTX-433), a potent noncompetitive inhibitor of the L-glutamate receptors and the nicotinic acetylcholine receptors of vertebrates and invertebrates, has a butyryl-tyrosyl-thermo-spermine structure. Several synthetic analogs of PhTX with hydrophobic alkyl branches in the polyamine chain exhibit 6- to 10-fold enhanced activities to various receptors. Because the branched analogs exhibit such unique activities and because of their importance in tertiary structural studies of ligand/receptor binding, methods for preparing branched PhTX analogs, including photolabile analogs, are presented.

  DOI：

  10.1021/jo00076a017
• 作为产物：
  描述：

  Ethyl 2-<2-<(tert-Butyldimethylsilyl)oxy>ethyl>cyanoacetate 在 锂硼氢 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以66%的产率得到2-(Hydroxymethyl)-4-<(tert-butyldimethylsilyl)oxy>butanenitrile
  参考文献：
  名称：

  Synthesis of philanthotoxin analogs with a branched polyamine moiety

  摘要：

  Philanthotoxin (PhTX-433), a potent noncompetitive inhibitor of the L-glutamate receptors and the nicotinic acetylcholine receptors of vertebrates and invertebrates, has a butyryl-tyrosyl-thermo-spermine structure. Several synthetic analogs of PhTX with hydrophobic alkyl branches in the polyamine chain exhibit 6- to 10-fold enhanced activities to various receptors. Because the branched analogs exhibit such unique activities and because of their importance in tertiary structural studies of ligand/receptor binding, methods for preparing branched PhTX analogs, including photolabile analogs, are presented.

  DOI：

  10.1021/jo00076a017