O-(1-allylcyclohex-1-yl) Se-phenyl selenocarbonate | 123283-06-7

• 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: O-(1-allylcyclohex-1-yl) Se-phenyl selenocarbonate
• 英文别名: (1-Prop-2-enylcyclohexyl) phenylselanylformate
• CAS: 123283-06-7
• 化学式: C₁₆H₂₀O₂Se
• 分子量: 323.294
• InChiKey: QFXNYRPCTFGIIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.43
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  O-(1-allylcyclohex-1-yl) Se-phenyl selenocarbonate 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 以95%的产率得到3-methyl-1-oxaspiro<4.5>decan-2-one
  参考文献：
  名称：

  Synthesis of .gamma.- and .delta.-lactones by free-radical annelation of Se-phenyl selenocarbonates

  摘要：

  A general method for the synthesis of gamma- and delta-lactones through the intramolecular addition of alkoxycarbonyl radicals, formed by reaction of Se-phenylselenocarbonates with n-Bu3SnH, onto carbon-carbon multiple bonds is described. This free-radical cyclization is characterized by high regioselectivity favoring exo addition and by a high ratio of cyclization to reduction. Monocyclic, fused bicyclic, and spirocyclic lactones are formed in good to excellent yield. Use of allyltri-n-butyltin as a chain-transfer agent in the place of n-Bu3SnH affords the corresponding 3-butenyl lactones.

  DOI：

  10.1021/jo00043a030
• 作为产物：
  描述：

  1-烯丙基环己醇 在 sodium hydride 作用下， 以 乙醇 、 苯 为溶剂， 反应 27.0h， 生成 O-(1-allylcyclohex-1-yl) Se-phenyl selenocarbonate
  参考文献：
  名称：

  Synthesis of .gamma.- and .delta.-lactones by free-radical annelation of Se-phenyl selenocarbonates

  摘要：

  A general method for the synthesis of gamma- and delta-lactones through the intramolecular addition of alkoxycarbonyl radicals, formed by reaction of Se-phenylselenocarbonates with n-Bu3SnH, onto carbon-carbon multiple bonds is described. This free-radical cyclization is characterized by high regioselectivity favoring exo addition and by a high ratio of cyclization to reduction. Monocyclic, fused bicyclic, and spirocyclic lactones are formed in good to excellent yield. Use of allyltri-n-butyltin as a chain-transfer agent in the place of n-Bu3SnH affords the corresponding 3-butenyl lactones.

  DOI：

  10.1021/jo00043a030

文献信息

• Bachi, Mario D.; Bosch, Eric, Heterocycles, 1989, vol. 28, # 2, p. 579 - 582
  作者：Bachi, Mario D.、Bosch, Eric

  DOI：——

  日期：——
• Synthesis of .gamma.- and .delta.-lactones by free-radical annelation of Se-phenyl selenocarbonates
  作者：Mario D. Bachi、Eric Bosch

  DOI：10.1021/jo00043a030

  日期：1992.8

  A general method for the synthesis of gamma- and delta-lactones through the intramolecular addition of alkoxycarbonyl radicals, formed by reaction of Se-phenylselenocarbonates with n-Bu3SnH, onto carbon-carbon multiple bonds is described. This free-radical cyclization is characterized by high regioselectivity favoring exo addition and by a high ratio of cyclization to reduction. Monocyclic, fused bicyclic, and spirocyclic lactones are formed in good to excellent yield. Use of allyltri-n-butyltin as a chain-transfer agent in the place of n-Bu3SnH affords the corresponding 3-butenyl lactones.