(1S,3R,5R,SR)-1-(p-tolylsulfinylmethyl)-10-oxa-9-azatricyclo[3.3.1.1^3,9]decane | 263241-27-6

• 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: (1S,3R,5R,SR)-1-(p-tolylsulfinylmethyl)-10-oxa-9-azatricyclo[3.3.1.1^3,9]decane
• 英文别名: (1R,3S,7R)-3-[[(R)-(4-methylphenyl)sulfinyl]methyl]-9-oxa-8-azatricyclo[5.2.1.03,8]decane
• CAS: 263241-27-6
• 化学式: C₁₆H₂₁NO₂S
• 分子量: 291.414
• InChiKey: LSMKHJSOQUFPDI-DHYLWCPWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  48.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,3R,5R,SR)-1-(p-tolylsulfinylmethyl)-10-oxa-9-azatricyclo[3.3.1.1^3,9]decane 在 Raney Ni (W-2) 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 、 水 为溶剂， 生成 euphococcinine
  参考文献：
  名称：

  Synthesis of Homochiral b-Sulfinyl Nitrones and Their Application for Enantioselective Synthesis of (+)-Euphococcinine

  摘要：

  Homochiral beta-sulfinyl nitrones can be prepared from secondary amines in three steps. Enantioselective synthesis of defensive alkaloid (+)-euphococcinine (9) has been accomplished by means of diastereoselective allylation of homochiral beta-sulfinyl nitrone (13) followed by intramolecular 1,3-dipolar cycloaddition reaction.

  DOI：

  10.3987/com-99-s81
• 作为产物：
  描述：

  2,3,4,5-四氢吡啶1-氧化物 在 nickel(III) oxide 、 三氯化铝 、 双氧水 、 5-ethyl-3-methyllumiflavinium perchlorate 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 为溶剂， 生成 (1S,3R,5R,SR)-1-(p-tolylsulfinylmethyl)-10-oxa-9-azatricyclo[3.3.1.1^3,9]decane
  参考文献：
  名称：

  Synthesis of Homochiral b-Sulfinyl Nitrones and Their Application for Enantioselective Synthesis of (+)-Euphococcinine

  摘要：

  Homochiral beta-sulfinyl nitrones can be prepared from secondary amines in three steps. Enantioselective synthesis of defensive alkaloid (+)-euphococcinine (9) has been accomplished by means of diastereoselective allylation of homochiral beta-sulfinyl nitrone (13) followed by intramolecular 1,3-dipolar cycloaddition reaction.

  DOI：

  10.3987/com-99-s81

文献信息

• Synthesis of Homochiral b-Sulfinyl Nitrones and Their Application for Enantioselective Synthesis of (+)-Euphococcinine
  作者：Shun-ichi Murahashi、Shun-Ichi Murahashi、Jun Sun、Hiroyuki Kurosawa、Yasushi Imada

  DOI：10.3987/com-99-s81

  日期：——

  Homochiral beta-sulfinyl nitrones can be prepared from secondary amines in three steps. Enantioselective synthesis of defensive alkaloid (+)-euphococcinine (9) has been accomplished by means of diastereoselective allylation of homochiral beta-sulfinyl nitrone (13) followed by intramolecular 1,3-dipolar cycloaddition reaction.