3-(diphenylphosphinoyl)-2-iodo-phenol | 854937-67-0

• 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: 3-(diphenylphosphinoyl)-2-iodo-phenol
• 英文别名: Phenol, 3-(diphenylphosphinyl)-2-iodo-；3-diphenylphosphoryl-2-iodophenol
• CAS: 854937-67-0
• 化学式: C₁₈H₁₄IO₂P
• 分子量: 420.186
• InChiKey: RDDUMZSAQWADEC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(diphenylphosphinoyl)-2-iodo-phenol 在 氢氧化钾 、 TEA 、 铜 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 生成 (S)-(6,6'-dihydroxybiphenyl-2,2'-diyl)bis(diphenylphosphine oxide)
  参考文献：
  名称：

  Avoiding the classical resolution during the synthesis of MeO-BIPHEP and 3,3′-disubstituted derivatives

  摘要：

  The Ullmann coupling of 1 (R = H) gives a 2:1 mixture of diastereomers 2 (R = H) in 81% yield that are easily separated by silica gel chromatography. This procedure avoids the generally cumbersome and sometimes difficult resolution step with DBTA. Similar Ullmann couplings and separation of the corresponding diastereomers are employed with other derivatives of I (R = OtBu, iPr, Ph, and mesityl) ultimately affording a new series of 3,3'-disubsituted-MeO-BIPHEP derivatives. The use of these new derivatives in palladium-catalyzed asymmetric Heck reaction, Pd-catalyzed polyene cyclizations and rhodium-catalyzed hydrogenations is also reported. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.03.183
• 作为产物：
  描述：

  (3-甲氧基苯基)(二苯基)膦 在 双氧水 、 三溴化硼 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 15.0h， 生成 3-(diphenylphosphinoyl)-2-iodo-phenol
  参考文献：
  名称：

  Avoiding the classical resolution during the synthesis of MeO-BIPHEP and 3,3′-disubstituted derivatives

  摘要：

  The Ullmann coupling of 1 (R = H) gives a 2:1 mixture of diastereomers 2 (R = H) in 81% yield that are easily separated by silica gel chromatography. This procedure avoids the generally cumbersome and sometimes difficult resolution step with DBTA. Similar Ullmann couplings and separation of the corresponding diastereomers are employed with other derivatives of I (R = OtBu, iPr, Ph, and mesityl) ultimately affording a new series of 3,3'-disubsituted-MeO-BIPHEP derivatives. The use of these new derivatives in palladium-catalyzed asymmetric Heck reaction, Pd-catalyzed polyene cyclizations and rhodium-catalyzed hydrogenations is also reported. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.03.183

文献信息

• Diastereospecific Intramolecular Ullmann Couplings:  Unique Chiral Auxiliary for the Preparation of 3,3‘-Disubstituted MeO-BIPHEP Derivatives
  作者：E. Gorobets、R. McDonald、B. A. Keay

  DOI：10.1021/ol060484p

  日期：2006.3.1

  auxiliary is described that provides only one diastereomer during intramolecular Ullmann couplings. Treatment of five Ullmann coupling precursors with Cu powder in DMF at 115 degrees C provides 2,2',3,3',6,6'-hexasubstituted 1,1'-biphenyls as single diastereomers in yields ranging from 66% to 91%.

  [反应：见正文]描述了一种手性助剂，在分子内Ullmann偶联过程中仅提供一种非对映异构体。在115摄氏度的DMF中用铜粉处理五种Ullmann偶联前体，得到2,2'，3,3'，6,6'-六取代的1,1'-联苯作为单一非对映异构体，收率范围为66％至91％ 。
• Avoiding the classical resolution during the synthesis of MeO-BIPHEP and 3,3′-disubstituted derivatives
  作者：Evgueni Gorobets、Bronwen M.M. Wheatley、J. Matthew Hopkins、Robert McDonald、Brian A. Keay

  DOI：10.1016/j.tetlet.2005.03.183

  日期：2005.5

  The Ullmann coupling of 1 (R = H) gives a 2:1 mixture of diastereomers 2 (R = H) in 81% yield that are easily separated by silica gel chromatography. This procedure avoids the generally cumbersome and sometimes difficult resolution step with DBTA. Similar Ullmann couplings and separation of the corresponding diastereomers are employed with other derivatives of I (R = OtBu, iPr, Ph, and mesityl) ultimately affording a new series of 3,3'-disubsituted-MeO-BIPHEP derivatives. The use of these new derivatives in palladium-catalyzed asymmetric Heck reaction, Pd-catalyzed polyene cyclizations and rhodium-catalyzed hydrogenations is also reported. (c) 2005 Elsevier Ltd. All rights reserved.