S-5-(benzylamino)-4-oxohexyl methane sulfonate hydrochloride | 1462379-88-9

• 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: S-5-(benzylamino)-4-oxohexyl methane sulfonate hydrochloride
• 英文别名: [(5S)-5-(benzylamino)-4-oxohexyl] methanesulfonate;hydrochloride
• CAS: 1462379-88-9
• 化学式: C₁₄H₂₁NO₄S*ClH
• 分子量: 335.852
• InChiKey: OKBUIWUVFMOZQB-YDALLXLXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.91
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  80.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  S-5-(benzylamino)-4-oxohexyl methane sulfonate hydrochloride 在 三仲丁基硼氢化钠 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 盐酸 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 以71%的产率得到(2S,3R)-1-benzyl-2-methyl-3-piperidinol
  参考文献：
  名称：

  Efficient, Stereodivergent Access to 3-Piperidinols by Traceless P(OEt)₃ Cyclodehydration

  摘要：

  A stereodivergent and highly diastereoselective (dr up to >19:1 for both isomers), step economic (5-6 steps), and scalable synthesis (up to 14 g) of cis- and trans-2-substituted 3-piperidinols, the core motif of numerous bioactive compounds, providing efficient access to the NK-1 inhibitor L-733,060 is presented. Additionally, a "traceless" (referring to the simplified byproduct separation) cyclodehydration realizing simple P(OEt)(3) as a substitute for PPh3 is developed.

  DOI：

  10.1021/ol4026588
• 作为产物：
  描述：

  (2S)-2-(benzyl(benzyloxycarbonyl)amino)propanoic acid 在 N-甲基吗啉 、 盐酸 、 palladium 10% on activated carbon 、 氢气 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 48.33h， 生成 S-5-(benzylamino)-4-oxohexyl methane sulfonate hydrochloride
  参考文献：
  名称：

  Efficient, Stereodivergent Access to 3-Piperidinols by Traceless P(OEt)₃ Cyclodehydration

  摘要：

  A stereodivergent and highly diastereoselective (dr up to >19:1 for both isomers), step economic (5-6 steps), and scalable synthesis (up to 14 g) of cis- and trans-2-substituted 3-piperidinols, the core motif of numerous bioactive compounds, providing efficient access to the NK-1 inhibitor L-733,060 is presented. Additionally, a "traceless" (referring to the simplified byproduct separation) cyclodehydration realizing simple P(OEt)(3) as a substitute for PPh3 is developed.

  DOI：

  10.1021/ol4026588

文献信息

• Efficient, Stereodivergent Access to 3-Piperidinols by Traceless P(OEt)₃ Cyclodehydration
  作者：Peter H. Huy、Ari M. P. Koskinen

  DOI：10.1021/ol4026588

  日期：2013.10.18

  A stereodivergent and highly diastereoselective (dr up to >19:1 for both isomers), step economic (5-6 steps), and scalable synthesis (up to 14 g) of cis- and trans-2-substituted 3-piperidinols, the core motif of numerous bioactive compounds, providing efficient access to the NK-1 inhibitor L-733,060 is presented. Additionally, a "traceless" (referring to the simplified byproduct separation) cyclodehydration realizing simple P(OEt)(3) as a substitute for PPh3 is developed.