3'-(phenylseleno)-(2α,3α)H-dihydro-2'(3'H)-oxofuro<4'5':2,3>cholestan-5α-ol | 157920-57-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 3'-(phenylseleno)-(2α,3α)H-dihydro-2'(3'H)-oxofuro<4'5':2,3>cholestan-5α-ol
• 英文别名: (1S,2R,4S,5R,8R,10R,13S,14S,17R,18R)-10-hydroxy-2,18-dimethyl-17-[(2R)-6-methylheptan-2-yl]-5-phenylselanyl-7-oxapentacyclo[11.7.0.02,10.04,8.014,18]icosan-6-one
• CAS: 157920-57-5
• 化学式: C₃₅H₅₂O₃Se
• 分子量: 599.756
• InChiKey: IEMUDRGUUNIMMM-ZEJORZQYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.19
• 重原子数：
  39
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3'-(phenylseleno)-(2α,3α)H-dihydro-2'(3'H)-oxofuro<4'5':2,3>cholestan-5α-ol 在 双氧水 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以83%的产率得到3αH-2'-oxofuro<2,3>cholestan-5α-ol
  参考文献：
  名称：

  Fragmentation of Alkoxy Radicals: Tandem .beta.-Fragmentation-Cycloperoxyiodination Reaction

  摘要：

  The steroidal alcohols 2-cholesten-5 alpha-ol (3), 3-phenyl-2-cholesten-5 alpha-ol (4), and 3 alpha H-2'-oxofuro-[2,3]cholestan-5 alpha-ol (5) were prepared in order to test a new tandem beta-fragmentation-cycloperoxyiodination reaction. The alkoxy radicals generated by irradiation of these alcohols with visible light in the presence of (diacetoxyiodo)benzene, I-2, and molecular oxygen undergo a beta-fragmentation reaction with subsequent peroxidation of the C-radical formed. This peroxy radical is added to conveniently positioned double bonds to give 10-membered cyclic ketones possessing a 1,2-dioxolane group.

  DOI：

  10.1021/jo00095a012
• 作为产物：
  描述：

  2β-carboxymethylcholestane-3α,5α-diol 在 三苯基膦 、 lithium diisopropyl amide 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 3.67h， 生成 3'-(phenylseleno)-(2α,3α)H-dihydro-2'(3'H)-oxofuro<4'5':2,3>cholestan-5α-ol
  参考文献：
  名称：

  Fragmentation of Alkoxy Radicals: Tandem .beta.-Fragmentation-Cycloperoxyiodination Reaction

  摘要：

  The steroidal alcohols 2-cholesten-5 alpha-ol (3), 3-phenyl-2-cholesten-5 alpha-ol (4), and 3 alpha H-2'-oxofuro-[2,3]cholestan-5 alpha-ol (5) were prepared in order to test a new tandem beta-fragmentation-cycloperoxyiodination reaction. The alkoxy radicals generated by irradiation of these alcohols with visible light in the presence of (diacetoxyiodo)benzene, I-2, and molecular oxygen undergo a beta-fragmentation reaction with subsequent peroxidation of the C-radical formed. This peroxy radical is added to conveniently positioned double bonds to give 10-membered cyclic ketones possessing a 1,2-dioxolane group.

  DOI：

  10.1021/jo00095a012

文献信息

• Boto Alicia, Betancor Carmen, Prange Thierry, Suarez Ernesto, J. Org. Chem, 59 (1994) N 16, S 4393-4401
  作者：Boto Alicia, Betancor Carmen, Prange Thierry, Suarez Ernesto

  DOI：——

  日期：——
• Fragmentation of Alkoxy Radicals: Tandem .beta.-Fragmentation-Cycloperoxyiodination Reaction
  作者：Alicia Boto、Carmen Betancor、Thierry Prange、Ernesto Suarez

  DOI：10.1021/jo00095a012

  日期：1994.8

  The steroidal alcohols 2-cholesten-5 alpha-ol (3), 3-phenyl-2-cholesten-5 alpha-ol (4), and 3 alpha H-2'-oxofuro-[2,3]cholestan-5 alpha-ol (5) were prepared in order to test a new tandem beta-fragmentation-cycloperoxyiodination reaction. The alkoxy radicals generated by irradiation of these alcohols with visible light in the presence of (diacetoxyiodo)benzene, I-2, and molecular oxygen undergo a beta-fragmentation reaction with subsequent peroxidation of the C-radical formed. This peroxy radical is added to conveniently positioned double bonds to give 10-membered cyclic ketones possessing a 1,2-dioxolane group.