(2R*,3S*)-2,3-bis<4-<(tert-butyldimethylsilyl)oxy>phenyl>-1-pentanol | 104946-96-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (2R*,3S*)-2,3-bis<4-<(tert-butyldimethylsilyl)oxy>phenyl>-1-pentanol
• 英文别名: (2R*,3S*)-2,3-bis[4-[(tert-butyldimethylsilyl)oxy]phenyl]-1-pentanol；(2R,3S)-2,3-bis[4-[tert-butyl(dimethyl)silyl]oxyphenyl]pentan-1-ol
• CAS: 104946-96-5
• 化学式: C₂₉H₄₈O₃Si₂
• 分子量: 500.869
• InChiKey: WNTRIGPJYZENJF-SXOMAYOGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.72
• 重原子数：
  34.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  38.69
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (2R*,3S*)-2,3-bis<4-<(tert-butyldimethylsilyl)oxy>phenyl>-1-pentanol 在 lithium aluminium tetrahydride 、 偶氮二甲酸二异丙酯 、 sodium methylate 、 三苯基膦 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醚 为溶剂， 反应 6.08h， 生成 (2R*,3S*)-2,3-bis<4-<(tert-butyldimethylsilyl)oxy>phenyl>pentyl 2-cyanoethyl sulfide
  参考文献：
  名称：

  Preparation, receptor binding, and fluorescence properties of hexestrol-fluorophore conjugates: evaluation of site of attachment, fluorophore structure, and fluorophore-ligand spacing

  摘要：

  We have undertaken a staged development of certain estrogen-fluorophore conjugates, in order to prepare a fluorescent estrogen suitable for determination of the estrogen receptor content of individual cells. Since non-steroidal estrogens with bulky substituents are often more readily bound by receptor than their steroidal counterparts, we have investigated fluorophore conjugates with derivatives of the non-steroidal estrogen hexestrol [3R*, 4S*)-3,4-bis(4-hydroxyphenyl)hexane). On the basis of the receptor-binding affinity of model compounds, we prepared a prototypical set of three ring- and side-chain-substituted fluorescent hexestrol derivatives, whose binding and fluorescence properties ultimately led to the preparation of a series of side-chain-substituted nitrobenzoxadiazole derivatives. The compounds prepared have binding affinities for the estrogen receptors that range from ca. 1% to 5% that of estradiol, and they have very favorable fluorescence characteristics, similar to those of fluorescein.

  DOI：

  10.1021/jm00384a026
• 作为产物：
  描述：

  2,3-bis<4-<(tert-butyldimethylsilyl)oxy>phenyl>-1-pentene 在 sodium hydroxide 、 硼烷四氢呋喃络合物 、 水 、 双氧水 作用下， 生成 (2R*,3S*)-2,3-bis<4-<(tert-butyldimethylsilyl)oxy>phenyl>-1-pentanol
  参考文献：
  名称：

  Preparation, receptor binding, and fluorescence properties of hexestrol-fluorophore conjugates: evaluation of site of attachment, fluorophore structure, and fluorophore-ligand spacing

  摘要：

  We have undertaken a staged development of certain estrogen-fluorophore conjugates, in order to prepare a fluorescent estrogen suitable for determination of the estrogen receptor content of individual cells. Since non-steroidal estrogens with bulky substituents are often more readily bound by receptor than their steroidal counterparts, we have investigated fluorophore conjugates with derivatives of the non-steroidal estrogen hexestrol [3R*, 4S*)-3,4-bis(4-hydroxyphenyl)hexane). On the basis of the receptor-binding affinity of model compounds, we prepared a prototypical set of three ring- and side-chain-substituted fluorescent hexestrol derivatives, whose binding and fluorescence properties ultimately led to the preparation of a series of side-chain-substituted nitrobenzoxadiazole derivatives. The compounds prepared have binding affinities for the estrogen receptors that range from ca. 1% to 5% that of estradiol, and they have very favorable fluorescence characteristics, similar to those of fluorescein.

  DOI：

  10.1021/jm00384a026

文献信息

• FEVIG T. L.; LLOYD J. E.; ZABLOCKI J. A.; KATZENELLENBOGEN J. A., J. MED. CHEM., 30,(1987) N 1, 156-165
  作者：FEVIG T. L.、 LLOYD J. E.、 ZABLOCKI J. A.、 KATZENELLENBOGEN J. A.

  DOI：——

  日期：——