(1S,2R,3S,4R)-3-methoxymethyl-2-triphenylstannylbicyclo[2.2.1]heptane(-) | 203380-20-5

• 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: (1S,2R,3S,4R)-3-methoxymethyl-2-triphenylstannylbicyclo[2.2.1]heptane(-)
• 英文别名: [(1S,2S,3S,4R)-3-(methoxymethyl)-2-bicyclo[2.2.1]heptanyl]-triphenylstannane
• CAS: 203380-20-5
• 化学式: C₂₇H₃₀OSn
• 分子量: 489.245
• InChiKey: IOOLMQOYPMPFND-OLTRZSQBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.22
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  碘 、 (1S,2R,3S,4R)-3-methoxymethyl-2-triphenylstannylbicyclo[2.2.1]heptane(-) 在 sodium hydride 作用下， 以 正己烷 、 氯仿 为溶剂， 以73%的产率得到diphenyl [(1SR,2RS,3SR,4RS)-3-methoxymethylbicyclo[2.2.1]-heptan-2-yl]tin iodide
  参考文献：
  名称：

  McNeill, Alan H.; Mortlock, Simon V.; Pratt, Robert M., Journal of the Chemical Society. Perkin transactions I, 1998, # 4, p. 709 - 715

  摘要：

  DOI：
• 作为产物：
  描述：

  (1RS,2RS,3SR,4SR)-3-hydroxymethyl-2-triphenylstannylbicyclo[2.2.1]-hept-5-ene 在 氢气 作用下， 以 乙醇 为溶剂， 以96%的产率得到(1S,2R,3S,4R)-3-methoxymethyl-2-triphenylstannylbicyclo[2.2.1]heptane(-)
  参考文献：
  名称：

  McNeill, Alan H.; Mortlock, Simon V.; Pratt, Robert M., Journal of the Chemical Society. Perkin transactions I, 1998, # 4, p. 709 - 715

  摘要：

  DOI：

文献信息

• Synthesis of chiral organotin reagents: synthesis of diphenyl- {(1S,2R,3S,4R)-3-(alkoxymethyl)bicyclo[2.2.1]heptan-2-yl}tin hydrides. X-Ray crystal structure of (R)-4,4-dimethyl-2-oxotetrahydrofuran-3-yl (1S,2S,3R,4R)-3-triphenylstannylbicyclo[2.2.1]hept-5-ene-2-carboxylate
  作者：Roy Beddoes、Robert M. Pratt、Eric J. Thomas

  DOI：10.1039/a706293a

  日期：——

  Conditions have been developed for the stereoselective Diels–Alder addition of cyclopentadiene to (R)-4,4-dimethyl-2-oxotetrahydrofuran-3-yl (E)-3-triphenylstannylprop-2-enoate 10 to give the endo-adduct 14 whose structure has been confirmed by X-ray crystallography. The adduct 14 is converted into (1S,2R,3S,4R)-3-hydroxymethylbicyclo[2.2.1]heptan-2-yl(triphenyl)stannane 22 which is shown to have an enantiomeric excess (ee) of 94%. This alcohol has been converted into its methyl ether (–)-3, trityl ether 25, tert-butyldimethylsilyl ether 26 and 1-naphthoate 27 which give the tin hydrides 4, 31–34 on treatment with iodine and sodium borohydride. Aspects of the chemistry of these enantiomerically enriched tin hydrides are briefly discussed.

  已经开发出了环戊二烯对(R)-4,4-二甲基-2-氧代四氢呋喃-3-基(E)-3-三苯基锡基丙-2-烯酸酯10进行立体选择性迪尔斯-阿尔德加成的条件,得到了endo-加成物14,其结构已通过X射线晶体学证实。将加成物14转化为(1S,2R,3S,4R)-3-羟甲基双环[2.2.1]庚-2-基(三苯基)锡烷22,其对映体过量(ee)达到94%。将此醇转化为其甲醚(–)-3,三苯甲醚25,叔丁基二甲基硅醚26和1-萘甲酸酯27,在碘和硼氢化钠处理下得到锡氢化物4,31-34。简要讨论了这些对映体富集的锡氢化物的化学特性。
• McNeill, Alan H.; Mortlock, Simon V.; Pratt, Robert M., Journal of the Chemical Society. Perkin transactions I, 1998, # 4, p. 709 - 715
  作者：McNeill, Alan H.、Mortlock, Simon V.、Pratt, Robert M.、Thomas, Eric J.

  DOI：——

  日期：——