(1SR,5SR,6RS)-3,3-dimethyl-5-phenyl-2,4-dioxabicyclo[4.4.0]decane | 162660-49-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1SR,5SR,6RS)-3,3-dimethyl-5-phenyl-2,4-dioxabicyclo[4.4.0]decane
• 英文别名: (4S,4aR,8aS)-2,2-dimethyl-4-phenyl-4a,5,6,7,8,8a-hexahydro-4H-benzo[d][1,3]dioxine
• CAS: 162660-49-3
• 化学式: C₁₆H₂₂O₂
• 分子量: 246.349
• InChiKey: ZGXLGRJFLOTNHC-QLFBSQMISA-N

物化性质

• 沸点：
  340.9±22.0 °C(predicted)
• 密度：
  1.013±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-cyclohexenyl(phenyl)methanol 在 air 、 三乙基硼 、 (C₄H₉)2Sn(OSO₂CF₃)H 、 对甲苯磺酸 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.0h， 生成 (1SR,5SR,6RS)-3,3-dimethyl-5-phenyl-2,4-dioxabicyclo[4.4.0]decane
  参考文献：
  名称：

  Highly Diastereoselective Hydrostannylation of Allyl and Homoallyl Alcohols with Dibutyl(trifluoromethanesulfoxy)stannane

  摘要：

  Dibutyl(trifluoromethanesulfoxy)stannane (Bu2Sn(OTf)H, 1a) was found to be very valuable for highly diastereoselective homolytic hydrostannylation of allyl and homoallyl alcohols. alpha,beta-Disubstituted allyl alcohols and alpha,gamma-disubstituted homoallyl alcohols were converted into gamma- and delta-stannylated alcohols with high 1,2-syn and 1,3-syn diastereoselectivity, respectively. The origin of the stereochemical outcomes can be rationalized by conformational fixation of the intermediary beta-stannylalkyl radical by coordination of the hydroxy group to the Lewis acidic tin center.

  DOI：

  10.1021/ja052245n

文献信息

• Thompson, Stephen H. J.; Mahon, Mary F.; Molloy, Kieran C., Journal of the Chemical Society. Perkin transactions I, 1995, # 4, p. 379 - 384
  作者：Thompson, Stephen H. J.、Mahon, Mary F.、Molloy, Kieran C.、Hadley, Michael S.、Gallagher, Timothy

  DOI：——

  日期：——
• Highly Diastereoselective Hydrostannylation of Allyl and Homoallyl Alcohols with Dibutyl(trifluoromethanesulfoxy)stannane
  作者：Katsukiyo Miura、Di Wang、Akira Hosomi

  DOI：10.1021/ja052245n

  日期：2005.7.1

  Dibutyl(trifluoromethanesulfoxy)stannane (Bu2Sn(OTf)H, 1a) was found to be very valuable for highly diastereoselective homolytic hydrostannylation of allyl and homoallyl alcohols. alpha,beta-Disubstituted allyl alcohols and alpha,gamma-disubstituted homoallyl alcohols were converted into gamma- and delta-stannylated alcohols with high 1,2-syn and 1,3-syn diastereoselectivity, respectively. The origin of the stereochemical outcomes can be rationalized by conformational fixation of the intermediary beta-stannylalkyl radical by coordination of the hydroxy group to the Lewis acidic tin center.