(2'-hydroxy-biphenyl-2-yl)-diethylphosphane | 1093348-90-3

• 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: (2'-hydroxy-biphenyl-2-yl)-diethylphosphane
• 英文别名: 2'-(Diethylphosphino)-[1,1'-biphenyl]-2-ol；2-(2-diethylphosphanylphenyl)phenol
• CAS: 1093348-90-3
• 化学式: C₁₆H₁₉OP
• 分子量: 258.3
• InChiKey: IIAOAVZNUSLZAJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  10-氯-9,10-二氢-9-氧杂-10-磷杂菲 、 乙基溴化镁 以 四氢呋喃 为溶剂， 以82%的产率得到(2'-hydroxy-biphenyl-2-yl)-diethylphosphane
  参考文献：
  名称：

  Bifunctional Phosphine-Catalyzed Domino Reaction: Highly Stereoselective Synthesis of cis-2,3-Dihydrobenzofurans from Salicyl N-Thiophosphinyl Imines and Allenes

  摘要：

  A new bifunctional phosphine catalyst, (2'-hydroxy-biphenyl-2-yl)-diethylphosphane (LBBA-1), was developed for the highly stereoselective synthesis of cis-2,3-dihydrobenzofurans via an aza-Morita-Baylis-Hillman/umpolung addition domino reaction of salicyl N-thiophosphinyl Imines with electron-deficient allenes. Dual activation of both nucleophile and electrophile by the bifunctional catalyst accounts for the observed high reactivity and stereoselectivity.

  DOI：

  10.1021/ol802453c
• 作为试剂：
  描述：

  N-(2-hydroxy-3-methylbenzylidene)-P,P-diphenylphosphinothioic amide 、 tert-butyl buta-2,3-dienoate 在 (2'-hydroxy-biphenyl-2-yl)-diethylphosphane 作用下， 以 甲苯 为溶剂， 反应 8.0h， 以83%的产率得到(E)-tert-butyl 3-(3-(diphenylphosphorothioylamino)-7-methyl-cis-2,3-dihydrobenzofuran-2-yl)acrylate
  参考文献：
  名称：

  Bifunctional Phosphine-Catalyzed Domino Reaction: Highly Stereoselective Synthesis of cis-2,3-Dihydrobenzofurans from Salicyl N-Thiophosphinyl Imines and Allenes

  摘要：

  A new bifunctional phosphine catalyst, (2'-hydroxy-biphenyl-2-yl)-diethylphosphane (LBBA-1), was developed for the highly stereoselective synthesis of cis-2,3-dihydrobenzofurans via an aza-Morita-Baylis-Hillman/umpolung addition domino reaction of salicyl N-thiophosphinyl Imines with electron-deficient allenes. Dual activation of both nucleophile and electrophile by the bifunctional catalyst accounts for the observed high reactivity and stereoselectivity.

  DOI：

  10.1021/ol802453c

文献信息

• Bifunctional Phosphine-Catalyzed Domino Reaction: Highly Stereoselective Synthesis of <i>cis</i>-2,3-Dihydrobenzofurans from Salicyl <i>N</i>-Thiophosphinyl Imines and Allenes
  作者：Xiangtai Meng、You Huang、Ruyu Chen

  DOI：10.1021/ol802453c

  日期：2009.1.1

  A new bifunctional phosphine catalyst, (2'-hydroxy-biphenyl-2-yl)-diethylphosphane (LBBA-1), was developed for the highly stereoselective synthesis of cis-2,3-dihydrobenzofurans via an aza-Morita-Baylis-Hillman/umpolung addition domino reaction of salicyl N-thiophosphinyl Imines with electron-deficient allenes. Dual activation of both nucleophile and electrophile by the bifunctional catalyst accounts for the observed high reactivity and stereoselectivity.