5-methyl-8-phenyl-9-(p-toluene-4-sulfonyl)-10-oxa-9-aza-tricyclo[5.2.1.0(1,5)]decan-6-one

• 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: 5-methyl-8-phenyl-9-(p-toluene-4-sulfonyl)-10-oxa-9-aza-tricyclo[5.2.1.0(1,5)]decan-6-one
• 英文别名: (1R,5S,7R,8R)-5-methyl-9-(4-methylphenyl)sulfonyl-8-phenyl-10-oxa-9-azatricyclo[5.2.1.01,5]decan-6-one
• 化学式: C₂₂H₂₃NO₄S
• 分子量: 397.495
• InChiKey: GLBIFESIWLCACQ-UGESXGAOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-methyl-8-phenyl-9-(p-toluene-4-sulfonyl)-10-oxa-9-aza-tricyclo[5.2.1.0(1,5)]decan-6-one 在 三乙基硅烷 、 四氯化钛 作用下， 以85%的产率得到4a-methyl-1-(p-toluene-4-sulfonyl)-2-phenyloctahydro-3,7a-epoxycyclopenta[b]pyridin-4-ol
  参考文献：
  名称：

  Stereoselective synthesis of piperidinone and quinolinone systems via ring opening reactions using TiCl4/silyl reagents

  摘要：

  Titanium(IV) chloride and silyl reagents mediated regio- and chemoselective ring opening reactions of oxa-bridged piperidinone ring systems were demonstrated. This methodology interestingly undergoes the stereoselective ring opening at the C-O bond of oxa-bridged piperidinone ring systems. Study of TiCl4 with hydride or non-hydride silyl reagents furnished the product with selectivity. This protocol is highly valuable to synthesize a range of stereoselective piperidinones, quinolinones ring systems. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.04.049
• 作为产物：
  描述：

  N-亚苄基-4-甲基苯磺酰胺 、 1-diazo-2-(1-methyl-2-oxocyclopentyl)ethan-2-one 在 dirhodium tetraacetate 作用下， 以 二氯甲烷 为溶剂， 以54%的产率得到5-methyl-8-phenyl-9-(p-toluene-4-sulfonyl)-10-oxa-9-aza-tricyclo[5.2.1.0(1,5)]decan-6-one
  参考文献：
  名称：

  Stereoselective synthesis of piperidinone and quinolinone systems via ring opening reactions using TiCl4/silyl reagents

  摘要：

  Titanium(IV) chloride and silyl reagents mediated regio- and chemoselective ring opening reactions of oxa-bridged piperidinone ring systems were demonstrated. This methodology interestingly undergoes the stereoselective ring opening at the C-O bond of oxa-bridged piperidinone ring systems. Study of TiCl4 with hydride or non-hydride silyl reagents furnished the product with selectivity. This protocol is highly valuable to synthesize a range of stereoselective piperidinones, quinolinones ring systems. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.04.049

文献信息

• Highly Regio- and Stereoselective [3+2] Cycloaddition of Carbonyl Ylides with Imines: A Novel Entry to Oxa-Bridged Piperidinone Ring Systems
  作者：Sengodagounder Muthusamy、Janagiraman Krishnamurthi、Eringathodi Suresh

  DOI：10.1055/s-2005-921891

  日期：——

  The reaction of α-diazo ketones and N-tosylimines in the presence of a rhodium(II) acetate catalyst led diastereoselectively to the oxa-bridged piperidinone ring systems. The stereochemistry was assigned bused on a single-crystal X-ray analysis.

  在醋酸铑 (II) 催化剂存在下，α-重氮酮和 N-甲苯磺酰亚胺的反应非对映选择性地导致氧杂桥接哌啶酮环系统。立体化学被指定用于单晶 X 射线分析。
• Stereoselective synthesis of piperidinone and quinolinone systems via ring opening reactions using TiCl4/silyl reagents
  作者：Sengodagounder Muthusamy、Chinnakuzhanthai Gangadurai、Janagiraman Krishnamurthi、Eringathodi Suresh

  DOI：10.1016/j.tet.2011.04.049

  日期：2011.6

  Titanium(IV) chloride and silyl reagents mediated regio- and chemoselective ring opening reactions of oxa-bridged piperidinone ring systems were demonstrated. This methodology interestingly undergoes the stereoselective ring opening at the C-O bond of oxa-bridged piperidinone ring systems. Study of TiCl4 with hydride or non-hydride silyl reagents furnished the product with selectivity. This protocol is highly valuable to synthesize a range of stereoselective piperidinones, quinolinones ring systems. (C) 2011 Elsevier Ltd. All rights reserved.