benzyl 2-thiazolyl ketone O-methyloxime | 144775-00-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl 2-thiazolyl ketone O-methyloxime
• 英文别名: N-methoxy-2-phenyl-1-(1,3-thiazol-2-yl)ethanimine
• CAS: 144775-00-8；144775-01-9
• 化学式: C₁₂H₁₂N₂OS
• 分子量: 232.306
• InChiKey: HCTAEOLMWPLYAP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  62.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-甲氧基-N-甲基-苯乙酰胺 在 吡啶 、 正丁基锂 、 四甲基乙二胺 作用下， 反应 26.5h， 生成 benzyl 2-thiazolyl ketone O-methyloxime
  参考文献：
  名称：

  A new efficient synthesis of (S)-dolaphenine ((S)-2-phenyl-1-(2-thiazolyl)ethylamine), the C-terminal unit of dolastatin 10

  摘要：

  Four methods for the preparation of (S)-dolaphenine ((S)-2-phenyl-1-(2-thiazolyl)ethylamine, 2), which constitutes the C-terminal unit of dolastatin 10 (1) having strong anticancer activity, has been investigated. Of these, the most efficient one involved the acylation of 2-lithiothiazole with N-methoxy-N-methylphenylacetamide (8), asymmetric reduction with (+)-diisopinocampheylchloroborane (11g), followed by the modified Mitsunobu reaction utilizing diphenyl phosphorazidate.

  DOI：

  10.1016/s0040-4020(01)88264-8

文献信息

• Stereoselective method for synthesizing dolaphenine
  申请人：Pharm-Eco Laboratories, Inc.

  公开号：US05750713A1

  公开（公告）日：1998-05-12

  The present invention relates to a method for the stereospecific synthesis of an enantiomer of a chiral amine, wherein the chiral amine has the formula R.sup.1 CH(NH.sub.2)R.sup.2. R.sup.1 and R.sup.2 are each independently selected from the group consisting of alkyl, aryl and heterocyclic and radicals. This method is particularly useful for stereospecifically synthesizing S-dolaphenine. The method involves contacting a chiral enantiomer of norephedrine with borane, within an aprotic solvent to form a complex for stereospecifically reducing oximes. The complex is then contacted with an oxime, thereby stereospecifically reducing said oxime to form an enantiomer of a chiral amine.

  该发明涉及一种手性胺对映体的立体特异性合成方法，其中该手性胺具有化学式R.sup.1 CH(NH.sub.2)R.sup.2。R.sup.1和R.sup.2分别独立地选自烷基、芳基和杂环基团。该方法特别适用于立体特异性合成S-多拉菲宁。该方法涉及将一种手性对映体的去甲麻黄碱与硼烷接触，在无极性溶剂中形成一个用于立体特异性还原肟的复合物。然后将该复合物与肟接触，从而立体特异性地还原所述肟，形成一种手性胺的对映体。
• A new efficient synthesis of (S)-dolaphenine ((S)-2-phenyl-1-(2-thiazolyl)ethylamine), the C-terminal unit of dolastatin 10
  作者：Naoko Irako、Yasumasa Hamada、Takayuki Shioiri

  DOI：10.1016/s0040-4020(01)88264-8

  日期：1992.1

  Four methods for the preparation of (S)-dolaphenine ((S)-2-phenyl-1-(2-thiazolyl)ethylamine, 2), which constitutes the C-terminal unit of dolastatin 10 (1) having strong anticancer activity, has been investigated. Of these, the most efficient one involved the acylation of 2-lithiothiazole with N-methoxy-N-methylphenylacetamide (8), asymmetric reduction with (+)-diisopinocampheylchloroborane (11g), followed by the modified Mitsunobu reaction utilizing diphenyl phosphorazidate.