(2S,3R)-2,3-Bis-[4-(1-ethoxy-ethoxy)-phenyl]-pentan-1-ol | 104947-31-1

• 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: (2S,3R)-2,3-Bis-[4-(1-ethoxy-ethoxy)-phenyl]-pentan-1-ol
• CAS: 104947-31-1
• 化学式: C₂₅H₃₆O₅
• 分子量: 416.558
• InChiKey: WTSNCMQFJRAJSY-KSXOSZKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.48
• 重原子数：
  30.0
• 可旋转键数：
  13.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  57.15
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (2S,3R)-2,3-Bis-[4-(1-ethoxy-ethoxy)-phenyl]-pentan-1-ol 在 palladium on activated charcoal lithium aluminium tetrahydride 、 偶氮二甲酸二异丙酯 、 氢气 、 potassium hydride 、 对甲苯磺酸 、 三苯基膦 作用下， 以 溶剂黄146 为溶剂， 生成 4-Amino-2-{7-[(2S,3R)-2,3-bis-(4-hydroxy-phenyl)-pentylsulfanyl]-heptyl}-isoindole-1,3-dione
  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：

  1-(1-ethoxyethoxy)-4-[2-[4-(1-ethoxyethoxy)phenyl]pent-1-en-3-yl]benzene 在 sodium hydroxide 、 硼烷 、 双氧水 作用下， 生成 (2S,3R)-2,3-Bis-[4-(1-ethoxy-ethoxy)-phenyl]-pentan-1-ol
  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