4-[2-(3,5-Dimethoxyphenyl)-5-methoxy-1-benzothiophen-3-yl]phenol | 1135316-02-7

• 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: 4-[2-(3,5-Dimethoxyphenyl)-5-methoxy-1-benzothiophen-3-yl]phenol
• CAS: 1135316-02-7
• 化学式: C₂₃H₂₀O₄S
• 分子量: 392.475
• InChiKey: LKJBCQWMMWWEHB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  76.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-吗啉乙醇 、 4-[2-(3,5-Dimethoxyphenyl)-5-methoxy-1-benzothiophen-3-yl]phenol 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 以78%的产率得到4-[2-[4-[2-(3,5-Dimethoxyphenyl)-5-methoxy-benzothiophen-3-yl]phenoxy]ethyl]morpholine
  参考文献：
  名称：

  Parallel Synthesis of a Desketoraloxifene Analogue Library via Iodocyclization/Palladium-Catalyzed Coupling

  摘要：

  For a future structure-activity relationship (SAR) study, a library of desketoraloxifene analogues has been prepared by parallel synthesis using iodocyclization and subsequent palladium-catalyzed coupling reactions. Points of desketoraloxifene diversification involve the two phenolic hydroxyl groups and the aliphatic amine side chain. This approach affords oxygen bearing 3-iodobenzo[b]thiophenes 4 in excellent yields, which are easily further elaborated using a two-step approach involving Suzuki-Miyaura and Mitsunobu coupling reactions to give multimethoxy-substituted desketoraloxifene analogues 6. Various hydroxyl-substituted desketoraloxifene analogues 7 were subsequently generated by demethylation with BBr(3).

  DOI：

  10.1021/co200090p
• 作为产物：
  描述：

  2-(3,5-Dimethoxyphenyl)-3-iodo-5-methoxy-1-benzothiophene 在 盐酸 、 四(三苯基膦)钯 、 水 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 水 、 甲苯 为溶剂， 反应 1.0h， 生成 4-[2-(3,5-Dimethoxyphenyl)-5-methoxy-1-benzothiophen-3-yl]phenol
  参考文献：
  名称：

  Parallel Synthesis of a Desketoraloxifene Analogue Library via Iodocyclization/Palladium-Catalyzed Coupling

  摘要：

  For a future structure-activity relationship (SAR) study, a library of desketoraloxifene analogues has been prepared by parallel synthesis using iodocyclization and subsequent palladium-catalyzed coupling reactions. Points of desketoraloxifene diversification involve the two phenolic hydroxyl groups and the aliphatic amine side chain. This approach affords oxygen bearing 3-iodobenzo[b]thiophenes 4 in excellent yields, which are easily further elaborated using a two-step approach involving Suzuki-Miyaura and Mitsunobu coupling reactions to give multimethoxy-substituted desketoraloxifene analogues 6. Various hydroxyl-substituted desketoraloxifene analogues 7 were subsequently generated by demethylation with BBr(3).

  DOI：

  10.1021/co200090p

文献信息

• A new approach to desketoraloxifene analogs from oxygen-bearing 3-iodobenzo[b]thiophenes prepared via iodocyclization
  作者：Chul-Hee Cho、Dai-Il Jung、Richard C. Larock

  DOI：10.1016/j.tetlet.2010.09.137

  日期：2010.12

  A formal total synthesis of the benzothiophene selective estrogen receptor modulator (SERM) desketoraloxifene and analogs has been accomplished from alkynes bearing electron-rich aromatic rings by electrophilic cyclization using I2. This approach affords oxygen-bearing 3-iodobenzo[b]thiophenes in excellent yields, which are easily further elaborated using a two-step approach involving Suzuki–Miyaura

  苯并噻吩选择性雌激素受体调节剂 (SERM) 去酮洛昔芬和类似物的正式全合成已通过使用 I 2 的亲电环化从带有富电子芳环的炔烃完成。这种方法以极好的收率提供了含氧的 3-碘苯并 [ b ] 噻吩，使用涉及 Suzuki-Miyaura 和 Mitsunobu 偶联反应的两步方法可以很容易地进一步阐述。
• Parallel Synthesis of a Desketoraloxifene Analogue Library via Iodocyclization/Palladium-Catalyzed Coupling
  作者：Chul-Hee Cho、Dai-Il Jung、Benjamin Neuenswander、Richard C. Larock

  DOI：10.1021/co200090p

  日期：2011.9.12

  For a future structure-activity relationship (SAR) study, a library of desketoraloxifene analogues has been prepared by parallel synthesis using iodocyclization and subsequent palladium-catalyzed coupling reactions. Points of desketoraloxifene diversification involve the two phenolic hydroxyl groups and the aliphatic amine side chain. This approach affords oxygen bearing 3-iodobenzo[b]thiophenes 4 in excellent yields, which are easily further elaborated using a two-step approach involving Suzuki-Miyaura and Mitsunobu coupling reactions to give multimethoxy-substituted desketoraloxifene analogues 6. Various hydroxyl-substituted desketoraloxifene analogues 7 were subsequently generated by demethylation with BBr(3).