(2R*,3S*)-2,3-bis<4-<(tert-butyldimethylsilyl)oxy>phenyl>pentyl 3-aminopropyl sulfide | 104947-04-8

• 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: (2R*,3S*)-2,3-bis<4-<(tert-butyldimethylsilyl)oxy>phenyl>pentyl 3-aminopropyl sulfide
• 英文别名: (2R*,3S*)-2,3-bis[4-[(tert-butyldimethylsilyl)oxy]phenyl]pentyl 3-aminopropyl sulfide；3-[(2R,3S)-2,3-bis[4-[tert-butyl(dimethyl)silyl]oxyphenyl]pentyl]sulfanylpropan-1-amine
• CAS: 104947-04-8
• 化学式: C₃₂H₅₅NO₂SSi₂
• 分子量: 574.031
• InChiKey: IAMFFUDNTMAQFW-IHLOFXLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.81
• 重原子数：
  38.0
• 可旋转键数：
  13.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  44.48
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2R*,3S*)-2,3-bis<4-<(tert-butyldimethylsilyl)oxy>phenyl>pentyl 3-aminopropyl sulfide 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 2.17h， 生成 (2R*,3S*)-2,3-bis(4-hydroxyphenyl)pentyl 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：

  (2R*,3S*)-2,3-bis<4-<(tert-butyldimethylsilyl)oxy>phenyl>pentyl 2-cyanoethyl sulfide 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以60%的产率得到(2R*,3S*)-2,3-bis<4-<(tert-butyldimethylsilyl)oxy>phenyl>pentyl 3-aminopropyl 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

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：——