(1S*,2R*,3S*,4R*)-7-(5-tert-butyldimethylsilyloxypent-2-ylidene)-2,3-di(hydroxymethyl)bicyclo[2.2.1]hept-5-ene acetonide | 1190404-52-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S*,2R*,3S*,4R*)-7-(5-tert-butyldimethylsilyloxypent-2-ylidene)-2,3-di(hydroxymethyl)bicyclo[2.2.1]hept-5-ene acetonide
• CAS: 1190404-52-4
• 化学式: C₂₃H₄₀O₃Si
• 分子量: 392.654
• InChiKey: OCRVBVOBXSPNGQ-JVSBHGNQSA-N

物化性质

• 沸点：
  432.1±45.0 °C(predicted)
• 密度：
  0.969±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.94
• 重原子数：
  27.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  27.69
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (1S*,2R*,3S*,4R*)-7-(5-tert-butyldimethylsilyloxypent-2-ylidene)-2,3-di(hydroxymethyl)bicyclo[2.2.1]hept-5-ene acetonide 在 吡啶 、 臭氧 、 sodium tetrahydroborate 、 水 作用下， 以 二氯甲烷 、 乙醇 为溶剂， 以63%的产率得到(cis,cis,cis)-9-(5-(tert-butyldimethylsilyloxy)pent-2-ylidene)-8,10-di(hydroxymethyl)-4,4-dimethyl-3,5-dioxa-bicyclo[5.3.0]decane
  参考文献：
  名称：

  Synthesis of cis,cis,cis-1-alkylidene-2,3,4,5-tetrakis(diphenylphosphinomethyl)cyclopentanes

  摘要：

  A new strategy to prepare tetradentate or pentadentate diphenylphosphine ligands has been explored from Diels-Alder adducts of fulvenes and maleic anhydride. A tetradentate phosphine ligand, bearing a side chain allowing the formation of a bond with polystyrene resin, has been prepared in seven steps from cyclopentadiene. The cis,cis,cis-1-cyclohexylidene-2,3,4,5-tetrakis(diphenylphosphinomethyl)cyclopentane (Cyclo-Tedicyp) in combination with [PdCl(C3H5)](2) led to an efficient catalyst for the Heck, Suzuki and Sonogashira coupling reactions. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.07.016
• 作为产物：
  描述：

  (5aR,6S,9R,9aS)-10-(5-((2-methoxypropan-2-yl)oxy)pentan-2-ylidene)-3,3-dimethyl-1,5,5a,6,9,9a-hexahydro-6,9-methanobenzo[e][1,3]dioxepine 、 叔丁基二甲基氯硅烷 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以90%的产率得到(1S*,2R*,3S*,4R*)-7-(5-tert-butyldimethylsilyloxypent-2-ylidene)-2,3-di(hydroxymethyl)bicyclo[2.2.1]hept-5-ene acetonide
  参考文献：
  名称：

  Synthesis of cis,cis,cis-1-alkylidene-2,3,4,5-tetrakis(diphenylphosphinomethyl)cyclopentanes

  摘要：

  A new strategy to prepare tetradentate or pentadentate diphenylphosphine ligands has been explored from Diels-Alder adducts of fulvenes and maleic anhydride. A tetradentate phosphine ligand, bearing a side chain allowing the formation of a bond with polystyrene resin, has been prepared in seven steps from cyclopentadiene. The cis,cis,cis-1-cyclohexylidene-2,3,4,5-tetrakis(diphenylphosphinomethyl)cyclopentane (Cyclo-Tedicyp) in combination with [PdCl(C3H5)](2) led to an efficient catalyst for the Heck, Suzuki and Sonogashira coupling reactions. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.07.016