(S)-2-Benzyl-hexahydro-pyrido[1,2-a]pyrazine-1,4-dione | 133523-43-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌嗪基哌啶类
• 英文名称: (S)-2-Benzyl-hexahydro-pyrido[1,2-a]pyrazine-1,4-dione
• 英文别名: (9aS)-2-benzyl-3,6,7,8,9,9a-hexahydropyrido[1,2-a]pyrazine-1,4-dione
• CAS: 133523-43-0
• 化学式: C₁₅H₁₈N₂O₂
• 分子量: 258.32
• InChiKey: BTBBEMYCMHMZRU-ZDUSSCGKSA-N

物化性质

• 沸点：
  499.2±44.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  甲醇 、 雷帕霉素 在 sodium hydroxide 、 sodium cyanoborohydride 、 苄胺 作用下， 生成 (S)-2-Benzyl-hexahydro-pyrido[1,2-a]pyrazine-1,4-dione 、
  参考文献：
  名称：

  Degradation of rapamycin: Retrieval of major intact subunits.

  摘要：

  The degradation of rapamycin has made available key substructures which have defined the structures of advanced synthetic intermediates.

  DOI：

  10.1016/s0040-4039(00)60797-9

文献信息

• On the remarkable propensity for carbon-carbon bond cleavage reactions in the C(8)-C(10) region of FK-506
  作者：Matthew J. Fisher、Ken Chow、Anabella Villalobos、Samuel J. Danishefsky

  DOI：10.1021/jo00008a055

  日期：1991.4

  It has been deduced from a series of transformations that formation of a tetrahedral intermediate at C-9 in FD-506 occasions fragmentation of the C-9-C-10 bond by a retro-Claisen-like pathway or the C-9-C-8 bond by a benzilic acid type rearrangement. Reduction of FK-506 with L-Selectride leads to the formation of a boronate ester 18 rather than to the corresponding diol 17, which had previously been formulated. Direct reduction of FK-506 with sodium triacetoxyborohydride (or hydrolysis of 18) does provide access to (22S)-dihydro FK-506 17. The former reduction also leads to some 22R epimer, which is an intermediate in the total synthesis of FK-506.