(-)-2-[(triphenylstannyl)methyl]pentane-1,5-diol | 1008799-11-8

• 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: (-)-2-[(triphenylstannyl)methyl]pentane-1,5-diol
• CAS: 1008799-11-8
• 化学式: C₂₄H₂₈O₂Sn
• 分子量: 467.195
• InChiKey: QFUMOYKENOLQFS-MAJYTBHHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.54
• 重原子数：
  27.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  40.46
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 以75%的产率得到(-)-2-[(triphenylstannyl)methyl]pentane-1,5-diol
  参考文献：
  名称：

  Synthesis of organotin derivatives of optically active eleven-membered macrodiolides

  摘要：

  DOI：

  10.1016/j.tetasy.2016.02.014

文献信息

• Stereoselective Radical Tandem Cyclohydrostannation of Optically Active Di-unsaturated Esters of TADDOL
  作者：Darío C. Gerbino、Liliana C. Koll、Sandra D. Mandolesi、Julio C. Podestá

  DOI：10.1021/om700693p

  日期：2008.2.1

  diastereoisomers, respectively, the addition of triphenyltin hydride to TADDOL disubstituted acrylates yields only four out of the 16 possible stereoisomers. The observed high stereoselectivity is consistent with the radical tandem cyclohydrostannation mechanism proposed. Only in the case of the hydrostannation of TADDOL diacrylate with trimethyl- and triphenyltin hydrides could the diastereoisomers obtained in

  本文报道了三有机锡氢化物R 3自由基加成研究的结果。SnH（R = Me，n-Bu，Ph; Neophyl），形成四个TADDOL不饱和二酯。发现这些反应导致高产率的环氢化锡的产物。还发现，虽然将这些氢化物添加到TADDOL二丙烯酸酯和TADDOL二甲基丙烯酸酯中分别导致了两种和四种环十一烷非对映异构体的预期混合物，但是将氢化三苯锡添加到TADDOL二取代丙烯酸酯中却只产生了16种可能的立体异构体中的四种。观察到的高立体选择性与提出的自由基串联环氢化锡机理是一致的。只有在TADDOL二丙烯酸酯与三甲基和三苯基锡氢化物加氢锡的情况下，才能获得更高比例的非对映异构体（5a和8a）以纯净形式隔离。大环内酯5a和8a的随后还原（氢化铝锂）以高收率得到相应的旋光性二醇26和27。给出了全部1 H，13 C和119 Sn NMR数据。
• Stereoselective Synthesis and Some Properties of New Chlorodiorganotin-Substituted Macrodiolides
  作者：Darío C. Gerbino、Jimena Scoccia、Liliana C. Koll、Sandra D. Mandolesi、Julio C. Podestá

  DOI：10.1021/om200987t

  日期：2012.1.23

  Radical tandem addition of dialkyltin chlorohydrides, R2SnHCl (R = n-Bu, neophyl, Ph), to TADDOL's substituted diacrylates (4-7) led to the corresponding products of cyclohydrostannation. The new optically active chlorodialkyltin-substituted 11-membered macrodiolides were obtained in very good yields and with much higher stereoselectivity than that achieved with the corresponding monohydrides, R3SnH. Thus, the cyclohydrostannation of diacrylate 4 and dimethacrylate 5 lead to just one diastereomer in the first case and to an easily separable mixture of two diastereomers in the second. Reduction of the new organotin macrocycles with LiAlH4 afforded optically active organotin derivatives structurally related to glutaric acid. Oxidation of the new chlorodiorganotin-substituted macrocycles with 30% hydrogen peroxide gave the new 11-membered macrocycles 30 and 31 free of tin in an average total yield of 43.4% from TADDOL. Full H-1, C-13, and Sn-119 data are also reported.