1-[bis(4-methoxyphenyl)methyl]-indane | 280552-84-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 1-[bis(4-methoxyphenyl)methyl]-indane
• CAS: 280552-84-3
• 化学式: C₂₄H₂₄O₂
• 分子量: 344.453
• InChiKey: DAPBQDLXKAVWAY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.57
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1-[bis(4-methoxyphenyl)methyl]-indane 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以57%的产率得到4-[2,3-dihydro-1H-inden-1-yl-(4-hydroxyphenyl)methyl]phenol
  参考文献：
  名称：

  Triarylethylene bisphenols with a novel cycle are ligands for the estrogen receptor

  摘要：

  We have prepared a series of triarylethylene and triarylethane systems, analogues of the selective antiestrogen tamoxifen, in which the alkyl substituent is tethered to the distal, rather than the proximal aryl ring by a 5-, 6-, or 7-membered carbocycle. This unusual cyclic structure rigidifies the ligand and adds bulk in a manner that is different from the more typical cyclization to the proximal aryl ring, as in the antiestrogen nafoxidine. These new systems were prepared efficiently by the addition of a benzylic sodium reagent, generated fi om the corresponding chloride by treatment with sodium naphthalenide, to a doubly protected 4,4'-dihydroxybenzophenone, followed by dehydration and deprotection. In all cases, formation of the exocyclic alkene was preferred. Two of the corresponding alkanes could be obtained by catalytic hydrogenation. All of these compounds have relatively high binding affinity for the estrogen receptor, and some of them demonstrate a significant level of affinity selectivity for the estrogen receptor alpha subtype. Accommodation of these newly rigidified cyclic triarylethylene systems into the ligand-binding pocket of the estrogen receptor can be visualized by molecular modeling. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00016-x
• 作为产物：
  描述：

  1-[bis(4-methoxyphenyl)methylidenyl]indane 在 platinum(IV) oxide 氢气 作用下， 以 甲醇 为溶剂， 以90%的产率得到1-[bis(4-methoxyphenyl)methyl]-indane
  参考文献：
  名称：

  Triarylethylene bisphenols with a novel cycle are ligands for the estrogen receptor

  摘要：

  We have prepared a series of triarylethylene and triarylethane systems, analogues of the selective antiestrogen tamoxifen, in which the alkyl substituent is tethered to the distal, rather than the proximal aryl ring by a 5-, 6-, or 7-membered carbocycle. This unusual cyclic structure rigidifies the ligand and adds bulk in a manner that is different from the more typical cyclization to the proximal aryl ring, as in the antiestrogen nafoxidine. These new systems were prepared efficiently by the addition of a benzylic sodium reagent, generated fi om the corresponding chloride by treatment with sodium naphthalenide, to a doubly protected 4,4'-dihydroxybenzophenone, followed by dehydration and deprotection. In all cases, formation of the exocyclic alkene was preferred. Two of the corresponding alkanes could be obtained by catalytic hydrogenation. All of these compounds have relatively high binding affinity for the estrogen receptor, and some of them demonstrate a significant level of affinity selectivity for the estrogen receptor alpha subtype. Accommodation of these newly rigidified cyclic triarylethylene systems into the ligand-binding pocket of the estrogen receptor can be visualized by molecular modeling. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00016-x