5-(4-chlorobutyl)-3-phenylhexahydrooxazolo[3,2-a]pyridine-5-carbonitrile | 855301-92-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 5-(4-chlorobutyl)-3-phenylhexahydrooxazolo[3,2-a]pyridine-5-carbonitrile
• 英文别名: (3R,5R,8aR)-5-(4-chlorobutyl)-3-phenyl-2,3,6,7,8,8a-hexahydro-[1,3]oxazolo[3,2-a]pyridine-5-carbonitrile
• CAS: 855301-92-7
• 化学式: C₁₈H₂₃ClN₂O
• 分子量: 318.846
• InChiKey: DSXICDGYZYUGFB-KSZLIROESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  36.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(4-chlorobutyl)-3-phenylhexahydrooxazolo[3,2-a]pyridine-5-carbonitrile 在 萘 、 lithium 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 生成 7-phenyl-9-oxa-6-azatricyclo[8.4.0.0^1,6]tetradec-4-en-10-ylamine
  参考文献：
  名称：

  Diasteroselective Synthesis of New Spiropiperidine Scaffolds from the CN(R,S) Building Block

  摘要：

  A methodology allowing the construction of spiropiperidine scaffolds similar to those found in naturally occurring alkaloids has been developed. This approach begins with the well-established CN(R,S) strategy, the spiro-center being built by way of an intramolecular attack of a nitrile function by an organolithium species obtained by a halogen/lithium exchange reaction mediated by either t-BuLi or lithium naphthalenide.

  DOI：

  10.1021/jo050258d
• 作为产物：
  描述：

  1-溴-4-氯丁烷 、 (-)-2-氰-6-苯基恶唑哌啶 在 lithium diisopropyl amide 作用下， 生成 5-(4-chlorobutyl)-3-phenylhexahydrooxazolo[3,2-a]pyridine-5-carbonitrile
  参考文献：
  名称：

  不对称合成。XXXIV。通过CN（R，S）方法合成螺哌啶衍生物

  摘要：

  由2-氰基-6-苯基恶唑并哌啶合子2b经烷基化，然后环化所得产物，制备了5-氮杂-螺-[3,5]壬烷和6-氮杂-螺[[4,5]癸烷衍生物5和9。溶解金属条件下的卤代氨基腈。

  DOI：

  10.1016/0040-4039(94)85367-3

文献信息

• Asymmetric synthesis. XXXIV. Synthesis of spiro-piperidine derivatives via the CN(R,S) method
  作者：Carlos M.R. Ribeiro、Sebastião J. de Melo、Martine Bonin、Jean-Charles Quirion、Henri-Philippe Husson

  DOI：10.1016/0040-4039(94)85367-3

  日期：1994.9

  5-Aza-spiro-[3,5] nonane and 6-aza-spiro-[4,5] decane derivatives 5 and 9 have been prepared from 2-cyano-6-phenyloxazolopiperidine synthon 2b via alkylation followed by cyclisation of the resulting halogeno aminonitrile under dissolving metal conditions.

  由2-氰基-6-苯基恶唑并哌啶合子2b经烷基化，然后环化所得产物，制备了5-氮杂-螺-[3,5]壬烷和6-氮杂-螺[[4,5]癸烷衍生物5和9。溶解金属条件下的卤代氨基腈。
• Diasteroselective Synthesis of New Spiropiperidine Scaffolds from the CN(<i>R</i>,<i>S</i>) Building Block
  作者：Emmanuel Roulland、Fabrice Cecchin、Henri-Philippe Husson

  DOI：10.1021/jo050258d

  日期：2005.5.1

  A methodology allowing the construction of spiropiperidine scaffolds similar to those found in naturally occurring alkaloids has been developed. This approach begins with the well-established CN(R,S) strategy, the spiro-center being built by way of an intramolecular attack of a nitrile function by an organolithium species obtained by a halogen/lithium exchange reaction mediated by either t-BuLi or lithium naphthalenide.