4-bromo-3-[(4-methoxyphenyl)ethynyl]anisole | 149457-46-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-bromo-3-[(4-methoxyphenyl)ethynyl]anisole
• 英文别名: 1-Bromo-4-methoxy-2-[2-(4-methoxyphenyl)ethynyl]benzene；1-bromo-4-methoxy-2-[2-(4-methoxyphenyl)ethynyl]benzene
• CAS: 149457-46-5
• 化学式: C₁₆H₁₃BrO₂
• 分子量: 317.182
• InChiKey: SGMCLTFRMCIIKW-UHFFFAOYSA-N

物化性质

• 沸点：
  430.0±45.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-bromo-3-[(4-methoxyphenyl)ethynyl]anisole 在 盐酸 、 四(三苯基膦)钯 、 正丁基锂 、 偶氮二甲酸二异丙酯 、 水 、 碘 、 potassium carbonate 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 环己烷 、 水 、 甲苯 为溶剂， 反应 2.67h， 生成 2-(4-(5-methoxy-2-(4-methoxyphenyl)benzo[b]thiophen-3-yl)phenoxy)-N,N-dimethylethan-1-amine
  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：

  1-Bromo-2-[1,2-dibromo-2-(4-methoxy-phenyl)-ethyl]-4-methoxy-benzene 在 18-冠醚-6 、 potassium tert-butylate 作用下， 以 苯 为溶剂， 生成 4-bromo-3-[(4-methoxyphenyl)ethynyl]anisole
  参考文献：
  名称：

  磷吲哚：烯丙二胺醚菊酯合成

  摘要：

  描述了通过仲邻膦基戊二酸酯的分子内环化的磷腈的第一个简单和一般的合成。

  DOI：

  10.1016/s0040-4039(00)93390-2

文献信息

• Silaindene - eine einfache Synthese
  作者：G. Märkl、K.-P. Berr

  DOI：10.1016/s0040-4039(00)91684-8

  日期：1992.3

  Tolanes substituted in o-position by -SiHPh2, polymerize intermolecular with H2PtCl6/CH2Cl2 as catalyst, depolymerisation at 350–380 °C/1 torr yields the silaindenes.

  邻位被-SiHPh 2取代的环戊二烯，以H 2 PtCl 6 / CH 2 Cl 2为催化剂在分子间聚合，在350–380°C / 1 torr下解聚，生成硅杂茚。
• A Novel Palladium-Mediated Coupling Approach to 2,3-Disubstituted Benzo[<i>b</i>]thiophenes and Its Application to the Synthesis of Tubulin Binding Agents
  作者：Bernard L. Flynn、Pascal Verdier-Pinard、Ernest Hamel

  DOI：10.1021/ol0067179

  日期：2001.3.1

  [GRAPHICS]Flexible, convergent access to 2,3-disubstituted benzo[b]thiophenes has been developed. The most concise approach involves sequential coupling of o-bromoiodobenzenes with benzylmercaptan and zinc acetylides to give benzyl o-ethynylphenyl sulfides which react with iodine to give 3-iodobenzo[b]thiophenes in a 5-endo-dig iodocyclization. These iodides can be further elaborated using palladium-mediated coupling and/or metalation techniques. This method has been applied to the synthesis of some novel tubulin binding agents.
• 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).
• Phosphindole
  作者：G. Märkl、G.Y. Jin、K.-P. Berr

  DOI：10.1016/s0040-4039(00)93390-2

  日期：1993.5

  A first simple and general synthesis of phosphindoles by intramolecular cyclisation of secondary o-phosphinotolanes is described.

  描述了通过仲邻膦基戊二酸酯的分子内环化的磷腈的第一个简单和一般的合成。