(1S*,2R*,3S*,4R*)-7-cyclohexylidene-2,3-di(hydroxymethyl)bicyclo[2.2.1]hept-5-ene acetonide | 1190404-24-0

• 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-cyclohexylidene-2,3-di(hydroxymethyl)bicyclo[2.2.1]hept-5-ene acetonide
• CAS: 1190404-24-0
• 化学式: C₁₈H₂₆O₂
• 分子量: 274.403
• InChiKey: QKJMLGCDLXUOPW-SYMSYNOKSA-N

物化性质

• 熔点：
  128 °C
• 沸点：
  372.1±42.0 °C(predicted)
• 密度：
  1.063±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.08
• 重原子数：
  20.0
• 可旋转键数：
  0.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (1S*,2R*,3S*,4R*)-7-cyclohexylidene-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56%的产率得到(cis,cis,cis)-1-cyclohexylidene-2,3,4,5-tetra-(hydroxymethyl)cyclopentane 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
• 作为产物：
  描述：

  2-甲氧基丙烯 、 (1S*,2R*,3S*,4R*)-7-cyclohexylidene-2,3-di(hydroxymethyl)bicyclo[2.2.1]hept-5-ene 在 camphor-10-sulfonic acid 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以96%的产率得到(1S*,2R*,3S*,4R*)-7-cyclohexylidene-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