(2E)-<2-<(2'R,5'R)-5'-<(tert-butyldimethylsilyl)oxy>-2'-methylcyclohexylidene>ethyl>diphenylphosphine oxide | 141277-80-7

• 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: (2E)-<2-<(2'R,5'R)-5'-<(tert-butyldimethylsilyl)oxy>-2'-methylcyclohexylidene>ethyl>diphenylphosphine oxide
• 英文别名: (2E)-(2-{(2'R,5'R)-5'-[(tert-butyldimethylsilyl)oxy]-2'-methylcyclohexylidene}ethyl)diphenylphosphine oxide；tert-butyl-[(1R,3E,4R)-3-(2-diphenylphosphorylethylidene)-4-methylcyclohexyl]oxy-dimethylsilane
• CAS: 141277-80-7
• 化学式: C₂₇H₃₉O₂PSi
• 分子量: 454.665
• InChiKey: WXBNAHCHJXEEBL-FCLFOFRFSA-N

物化性质

• 沸点：
  503.0±50.0 °C(predicted)
• 密度：
  1.03±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.14
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2E)-<2-<(2'R,5'R)-5'-<(tert-butyldimethylsilyl)oxy>-2'-methylcyclohexylidene>ethyl>diphenylphosphine oxide 在 正丁基锂 、 AG-50WX₄ ion exchange resin 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 4.5h， 生成 25-hydroxy-10(R),19-dihydro-(5E)-3-epivitamin D₂
  参考文献：
  名称：

  A convergent approach to the dihydrotachysterol diene system. Application to the synthesis of dihydrotachysterol2 (DHT2), 25-hydroxydihydrotachysterol2 (25-OH-DHT2), 10(R),19-dihydro-(5E)-3-epivitamin D2 and 25-hydroxy-10(R),19-dihydro-(5E)-3-epivitamin D2

  摘要：

  Total synthesis of A-ring fragments of 10(S),19-dihydrovitamins D and 10(R),19-dihydro-(5E)-epivitamins D from (+)-(S)-carvone and (-)-(R)-carvone is described. These fragments were used for convergent synthesis of dihydrotachysterol2 (DHT2), 25-hydroxydihydrotachysterol2, 10(R),19-dihydro-(5E)-3-epivitamin D2, and 25-hydroxy-10(R),19-dihydro-(5E)-3-epivitamin D2.

  DOI：

  10.1021/jo00045a038
• 作为产物：
  描述：

  ethyl (E)-2-[(2R,5R)-2-methyl-5-(prop-1-en-2-yl)cyclohexylidene]acetate 在 咪唑 、 N-氯代丁二酰亚胺 、 二甲基硫 、 双氧水 、 二异丁基氢化铝 作用下， 生成 (2E)-<2-<(2'R,5'R)-5'-<(tert-butyldimethylsilyl)oxy>-2'-methylcyclohexylidene>ethyl>diphenylphosphine oxide
  参考文献：
  名称：

  A Synthesis of A-Ring Synthons for Dihydrotachysterols

  摘要：

  Phosphine oxides 1 and 2, enantiomeric synthons for the preparation of dihydrotachysterols, were synthesized from the appropriate dihydrocarvones.

  DOI：

  10.1016/s0040-4039(00)91693-9

文献信息

• A Synthesis of A-Ring Synthons for Dihydrotachysterols
  作者：Rob Boer Rookhuizen、Jaap C. Hanekamp、Hendrik J.T. Bos

  DOI：10.1016/s0040-4039(00)91693-9

  日期：1992.3

  Phosphine oxides 1 and 2, enantiomeric synthons for the preparation of dihydrotachysterols, were synthesized from the appropriate dihydrocarvones.
• A convergent approach to the dihydrotachysterol diene system. Application to the synthesis of dihydrotachysterol2 (DHT2), 25-hydroxydihydrotachysterol2 (25-OH-DHT2), 10(R),19-dihydro-(5E)-3-epivitamin D2 and 25-hydroxy-10(R),19-dihydro-(5E)-3-epivitamin D2
  作者：Miguel A. Maestro、Luis Castedo、Antonio Mourino

  DOI：10.1021/jo00045a038

  日期：1992.9

  Total synthesis of A-ring fragments of 10(S),19-dihydrovitamins D and 10(R),19-dihydro-(5E)-epivitamins D from (+)-(S)-carvone and (-)-(R)-carvone is described. These fragments were used for convergent synthesis of dihydrotachysterol2 (DHT2), 25-hydroxydihydrotachysterol2, 10(R),19-dihydro-(5E)-3-epivitamin D2, and 25-hydroxy-10(R),19-dihydro-(5E)-3-epivitamin D2.