diethyl 4-tert-butyldimethylsilanyloxy-1-cyanobutylphosphonate | 765954-47-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: diethyl 4-tert-butyldimethylsilanyloxy-1-cyanobutylphosphonate
• 英文别名: 5-[Tert-butyl(dimethyl)silyl]oxy-2-diethoxyphosphorylpentanenitrile
• CAS: 765954-47-0
• 化学式: C₁₅H₃₂NO₄PSi
• 分子量: 349.483
• InChiKey: RVEVWCPTDVZRJP-UHFFFAOYSA-N

物化性质

• 沸点：
  409.9±40.0 °C(Predicted)
• 密度：
  1.001±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.95
• 重原子数：
  22
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  68.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  diethyl 4-tert-butyldimethylsilanyloxy-1-cyanobutylphosphonate 在 六甲基磷酰三胺 、 sodium hydride 、 二异丁基氢化铝 、 sodium iodide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 19.58h， 生成 11-cis-12-formyl-13-demethyl-13,14-dihydroretinol
  参考文献：
  名称：

  12-Substituted-13,14-dihydroretinols designed for affinity labeling of retinol binding- and processing proteins

  摘要：

  All-trans- and 11-cis-retinol derivatives substituted with various electron-withdrawing groups at C-12 were designed to be affinity labels for retinol binding and processing proteins. Unlike other non-selective highly reactive affinity labels, these compounds carry a Michael acceptor type substitution at C-12 of the polyene chain. Therefore, they are expected to be highly selective towards such proteins that have a nucleophilic residue near the C-12 position of their retinol ligand. The synthetic route for these compounds is based on the Emmons-Horner reaction of a C15 aldehyde with an appropriate phosphonate bearing the desired electron-withdrawing group to be incorporated at the C-12 position of the retinol skeleton. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.06.116
• 作为产物：
  描述：

  氰甲基磷酸二乙酯 、 (3-溴丙氧基)叔丁基二甲基硅烷 在 六甲基磷酰三胺 、 sodium hydride 、 sodium iodide 作用下， 以 四氢呋喃 为溶剂， 反应 72.0h， 以40%的产率得到diethyl 4-tert-butyldimethylsilanyloxy-1-cyanobutylphosphonate
  参考文献：
  名称：

  12-Substituted-13,14-dihydroretinols designed for affinity labeling of retinol binding- and processing proteins

  摘要：

  All-trans- and 11-cis-retinol derivatives substituted with various electron-withdrawing groups at C-12 were designed to be affinity labels for retinol binding and processing proteins. Unlike other non-selective highly reactive affinity labels, these compounds carry a Michael acceptor type substitution at C-12 of the polyene chain. Therefore, they are expected to be highly selective towards such proteins that have a nucleophilic residue near the C-12 position of their retinol ligand. The synthetic route for these compounds is based on the Emmons-Horner reaction of a C15 aldehyde with an appropriate phosphonate bearing the desired electron-withdrawing group to be incorporated at the C-12 position of the retinol skeleton. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.06.116

文献信息

• 12-Substituted-13,14-dihydroretinols designed for affinity labeling of retinol binding- and processing proteins
  作者：Revital Yefidoff、Amnon Albeck

  DOI：10.1016/j.tet.2004.06.116

  日期：2004.9

  All-trans- and 11-cis-retinol derivatives substituted with various electron-withdrawing groups at C-12 were designed to be affinity labels for retinol binding and processing proteins. Unlike other non-selective highly reactive affinity labels, these compounds carry a Michael acceptor type substitution at C-12 of the polyene chain. Therefore, they are expected to be highly selective towards such proteins that have a nucleophilic residue near the C-12 position of their retinol ligand. The synthetic route for these compounds is based on the Emmons-Horner reaction of a C15 aldehyde with an appropriate phosphonate bearing the desired electron-withdrawing group to be incorporated at the C-12 position of the retinol skeleton. (C) 2004 Elsevier Ltd. All rights reserved.