2H-Hexahydro-2-(3-chloropropyl)-2-cyano-6-phenyloxazolo<3,2-a>pyridne | 855301-93-8

• 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: 2H-Hexahydro-2-(3-chloropropyl)-2-cyano-6-phenyloxazolo<3,2-a>pyridne
• 英文别名: 2H-Hexahydro-2-(3-chloropropyl)-2-cyano-6-phenyloxazolo[3,2-a]pyridne；(3R,5R,8aR)-5-(3-chloropropyl)-3-phenyl-2,3,6,7,8,8a-hexahydro-[1,3]oxazolo[3,2-a]pyridine-5-carbonitrile
• CAS: 855301-93-8
• 化学式: C₁₇H₂₁ClN₂O
• 分子量: 304.82
• InChiKey: ZPXBQLFEHGVDOR-GVDBMIGSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 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：

  2H-Hexahydro-2-(3-chloropropyl)-2-cyano-6-phenyloxazolo<3,2-a>pyridne 在 萘 、 lithium 、 柠檬酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 3a-amino-6-phenyldecahydro-4-oxa-6a-azacyclopenta[d]naphthalene-7-carbonitrile
  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-氯-3-碘丙烷 、 (-)-2-氰-6-苯基恶唑哌啶 在 lithium diisopropyl amide 作用下， 生成 2H-Hexahydro-2-(3-chloropropyl)-2-cyano-6-phenyloxazolo<3,2-a>pyridne
  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

• A diastereoselective approach for an asymmetric synthesis in pinnaic acid series
  作者：Emmanuel Roulland、Angèle Chiaroni、Henri-Philippe Husson

  DOI：10.1016/j.tetlet.2005.04.019

  日期：2005.6

  An enantiopure spiran-bearing advanced intermediate in pinnaic acid series was obtained in 11 steps starting with CN(R,S) building block.

  从CN（R，S）结构单元开始，通过11个步骤获得了一个对映体纯正的含吡喃酮的螺旋烷高级中间体。
• Asymmetric synthesis. 29. Preparation of 1,8-diazaspiro[5.5]undecane derivatives
  作者：Jieping Zhu、Jean Charles Quirion、Henri Philippe Husson

  DOI：10.1021/jo00075a048

  日期：1993.11

  From 2-cyano-6-phenyl oxazolopiperidine 1, two highly efficient routes have been developed for the asymmetric synthesis of the spiropiperidine system: 1,8-diazaspiro[5.5]undecane. The key step was generation of the imine salts 6 and 17 from the functionalized alpha-amino nitrile 2, by nucleophilic addition of a suitable organometallic reagent to the nitrile group followed by, in situ, intramolecular nucleophilic alkylation. A reductive-cyclization procedure allowed the preparation of nonsubstituted and monosubstituted spiro compounds 5 and 10, respectively, while an alkylation-cyclization procedure led to the disubstituted spiro derivative 15, an aza analog of perhydrohistrionicotoxin.