Se-phenyl 3,7-dimethyloct-6-eneselenoate | 115033-76-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: Se-phenyl 3,7-dimethyloct-6-eneselenoate
• 英文别名: phenylselenyl citronelloate
• CAS: 115033-76-6
• 化学式: C₁₆H₂₂OSe
• 分子量: 309.31
• InChiKey: HTDHNCPLNZKRNL-UHFFFAOYSA-N

物化性质

• 沸点：
  390.2±35.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.32
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  Se-phenyl 3,7-dimethyloct-6-eneselenoate 、 丙烯腈 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 以57%的产率得到9-十一碳烯腈,6,10-二甲基-4-羰基-
  参考文献：
  名称：

  Tandem free-radical ring expansion and 5-exo-dig 5-hexynyl radical cyclization: a useful approach to fused bicyclic carbocycles

  摘要：

  DOI：

  10.1021/jo00307a010
• 作为产物：
  描述：

  3,7-二甲基-6-辛烯酸 、 N-(苯硒基)邻苯二甲酰亚胺 在 三丁基膦 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以81%的产率得到Se-phenyl 3,7-dimethyloct-6-eneselenoate
  参考文献：
  名称：

  Acyl radicals: intermolecular and intramolecular alkene addition reactions

  摘要：

  A full study of the use of phenyl selenoesters as precursors to acyl radicals and their subsequent participation in intermolecular and intramolecular alkene addition reactions is detailed. Primary alkyl-, vinyl-, and aryl-substituted acyl radicals generated by Bu3SnH treatment of the corresponding phenyl selenoesters participate cleanly in intermolecular addition reactions with alkenes bearing electron-withdrawing or radical-stabilizing substituents at rates that exceed those of the potentially competitive decarbonylation or reduction. Similarly, their intramolecular addition to activated or unactivated alkenes proceeds without significant competitive reduction or decarbonylation and at rates generally greater-than-or-equal-to 1 x 10(6) s-1 with some occurring at rates greater-than-or-equal-to 3 x 10(7) s-1. Consistent with their behavior in intermolecular addition reactions, the 5-exo-trig cyclizations of secondary and tertiary alkyl-substituted acyl radicals to an unactivated olefin acceptor may be accompanied by varying degrees of decarbonylation, even under low-temperature free-radical reaction conditions. Studies are presented which suggest that the intramolecular additions of acyl radicals to alkenes under the conditions detailed herein may be regarded as irreversible, kinetically controlled processes which exhibit regioselectivity that is predictable based on well-established empirical rules set forth for the analogous free-radical cyclization reactions of alkyl radicals.

  DOI：

  10.1021/jo00031a021

文献信息

• Bachi, Mario D.; Denenmark, Daniella, Heterocycles, 1989, vol. 28, # 2, p. 583 - 588
  作者：Bachi, Mario D.、Denenmark, Daniella

  DOI：——

  日期：——
• BOGER, DALE L.;MATHVINK, ROBERT J., J. ORG. CHEM., 55,(1990) N0, C. 5442-5444
  作者：BOGER, DALE L.、MATHVINK, ROBERT J.

  DOI：——

  日期：——
• BOGER, D. L.;MATHVINK, R. J., J. ORG. CHEM., 53,(1988) N 14, 3377-3379
  作者：BOGER, D. L.、MATHVINK, R. J.

  DOI：——

  日期：——
• Acyl radicals: intermolecular and intramolecular alkene addition reactions
  作者：Dale L. Boger、Robert J. Mathvink

  DOI：10.1021/jo00031a021

  日期：1992.2

  A full study of the use of phenyl selenoesters as precursors to acyl radicals and their subsequent participation in intermolecular and intramolecular alkene addition reactions is detailed. Primary alkyl-, vinyl-, and aryl-substituted acyl radicals generated by Bu3SnH treatment of the corresponding phenyl selenoesters participate cleanly in intermolecular addition reactions with alkenes bearing electron-withdrawing or radical-stabilizing substituents at rates that exceed those of the potentially competitive decarbonylation or reduction. Similarly, their intramolecular addition to activated or unactivated alkenes proceeds without significant competitive reduction or decarbonylation and at rates generally greater-than-or-equal-to 1 x 10(6) s-1 with some occurring at rates greater-than-or-equal-to 3 x 10(7) s-1. Consistent with their behavior in intermolecular addition reactions, the 5-exo-trig cyclizations of secondary and tertiary alkyl-substituted acyl radicals to an unactivated olefin acceptor may be accompanied by varying degrees of decarbonylation, even under low-temperature free-radical reaction conditions. Studies are presented which suggest that the intramolecular additions of acyl radicals to alkenes under the conditions detailed herein may be regarded as irreversible, kinetically controlled processes which exhibit regioselectivity that is predictable based on well-established empirical rules set forth for the analogous free-radical cyclization reactions of alkyl radicals.
• Tandem free-radical ring expansion and 5-exo-dig 5-hexynyl radical cyclization: a useful approach to fused bicyclic carbocycles
  作者：Dale L. Boger、Robert J. Mathvink

  DOI：10.1021/jo00307a010

  日期：1990.9