(2R,5S)-1-aza-3-oxa-9-oxo-2-phenylbicyclo[4.3.0]nonane | 158362-66-4

• 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: (2R,5S)-1-aza-3-oxa-9-oxo-2-phenylbicyclo[4.3.0]nonane
• 英文别名: (3R,8aS)-3-phenyl-1,3,6,7,8,8a-hexahydro-[1,3]oxazolo[3,4-a]pyridin-5-one
• CAS: 158362-66-4
• 化学式: C₁₃H₁₅NO₂
• 分子量: 217.268
• InChiKey: XFJBMEJOWGBGHR-WCQYABFASA-N

物化性质

• 沸点：
  395.114±31.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.216±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2R,5S)-1-aza-3-oxa-9-oxo-2-phenylbicyclo[4.3.0]nonane 在 间氯过氧苯甲酸 、 lithium hexamethyldisilazane 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Short approach to functionalised homochiral piperidinones

  摘要：

  The preparation of homochiral lactam 4 in 5 steps from (S)-lysine is described. Conversion to bicyclic O,N-acetal 5 provides a useful template for further elaboration to highly substituted piperidinones with excellent diastereoselectivity.

  DOI：

  10.1016/0957-4166(94)80113-4
• 作为产物：
  描述：

  (-)-(S)-6-oxo-2-piperidinecarboxylic acid methyl ester 在 sodium tetrahydroborate 、 对甲苯磺酸 作用下， 以 乙醇 为溶剂， 反应 72.0h， 生成 (2R,5S)-1-aza-3-oxa-9-oxo-2-phenylbicyclo[4.3.0]nonane
  参考文献：
  名称：

  Short approach to functionalised homochiral piperidinones

  摘要：

  The preparation of homochiral lactam 4 in 5 steps from (S)-lysine is described. Conversion to bicyclic O,N-acetal 5 provides a useful template for further elaboration to highly substituted piperidinones with excellent diastereoselectivity.

  DOI：

  10.1016/0957-4166(94)80113-4

文献信息

• Enantiopure bicyclic piperidinones: stereoselectivity in lactam enolate alkylations
  作者：Andrew G. Brewster、Simon Broady、Catherine E. Davies (née Mills)、Thomas D. Heightman、Stephen A. Hermitage、Mark Hughes、Mark G. Moloney、Gordon Woods

  DOI：10.1039/b316037h

  日期：——

  The synthesis and alkylation of [4.3.0]-bicyclic lactams, derived from 6-oxopipecolic acid, have been investigated. Alkylation can proceed with predominantly exo-diastereoselectivity, but the efficiency of this process depends on the substitution at the hemiaminal ether system. These products can be readily deprotected to give substituted hydroxymethyl lactams in good yield.

  已经研究了衍生自6-氧代戊酸的[4.3.0]-双环内酰胺的合成和烷基化。烷基化可以主要通过外非对映选择性进行，但是该过程的效率取决于半胱氨酸醚系统中的取代。这些产物可以容易地脱保护，以高收率得到取代的羟甲基内酰胺。
• Diastereoselectivity in the alkylations of bicyclic piperidinones
  作者：Catherine E. Mills (née Davis)、Thomas D. Heightman、Stephen A. Hermitage、Mark G. Moloney、Gordon A. Woods

  DOI：10.1016/s0040-4039(97)10694-3

  日期：1998.2

  The synthesis of substituted [4.3.0] bicyclic lactams derived from 6-oxo-2-hydroxymethylpiperidine is described. The enolate derived from these systems can be alkylated with a range of reactive electrophiles; the diastereoselectivity which can be achieved depends on the substitution pattern of the oxazolidine ring system and the nature of the alkylating reagent, and can vary from 1:1 to as much as

  描述了由6-氧代-2-羟基甲基哌啶衍生的取代的[4.3.0]双环内酰胺的合成。这些体系衍生的烯醇化物可以用一系列反应性亲电试剂进行烷基化。可达到的非对映选择性取决于恶唑烷环系统的取代方式和烷基化试剂的性质，其可在1：1至高达10：1的范围内变化。
• Short approach to functionalised homochiral piperidinones
  作者：Stephen A. Hermitage、Mark G. Moloney

  DOI：10.1016/0957-4166(94)80113-4

  日期：1994.8

  The preparation of homochiral lactam 4 in 5 steps from (S)-lysine is described. Conversion to bicyclic O,N-acetal 5 provides a useful template for further elaboration to highly substituted piperidinones with excellent diastereoselectivity.