N-(2-hydroxy-5-methylbenzylidene)-P,P-diphenylphosphinothioic amide | 1093349-08-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N-(2-hydroxy-5-methylbenzylidene)-P,P-diphenylphosphinothioic amide
• 英文别名: [(2-Hydroxy-5-methylphenyl)methylideneamino]-diphenyl-sulfidophosphanium
• CAS: 1093349-08-6
• 化学式: C₂₀H₁₈NOPS
• 分子量: 351.409
• InChiKey: QDJRSTKIOYRXTE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  33.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,3-丁二烯酸乙酯 、 N-(2-hydroxy-5-methylbenzylidene)-P,P-diphenylphosphinothioic amide 在 (2'-hydroxy-biphenyl-2-yl)-diethylphosphane 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以90%的产率得到(E)-ethyl 3-(3-(diphenylphosphorothioylamino)-5-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
• 作为产物：
  描述：

  5-甲基水杨醛 、 P,P-diphenylphosphinothioic amide 在 硅酸四乙酯 作用下， 反应 8.0h， 以95%的产率得到N-(2-hydroxy-5-methylbenzylidene)-P,P-diphenylphosphinothioic amide
  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

• 一种具有C2季碳中心的苯并二氢呋喃衍生物的合成方法
  申请人：国网湖南省电力有限公司

  公开号：CN109776465B

  公开（公告）日：2023-06-06

  本发明属于化合物合成领域，具体提供了一种具有C2季碳中心的苯并二氢呋喃衍生物的制备方法，将具有双官能团化合物、α‑羰基甲酸酯溶于有机溶剂，加入六甲基亚磷酰胺进行反应，随后向反应体系中加入碱，继续反应，得到目的产物。本发明技术为全新的机理，基于原位形成的Kukhtin‑Ramirez加合物与双官能团化合物中极性羟基的插入反应，并采用两步一锅法合成策略发生分子内环化反应，以中等至较高的收率合成了一系列具有C2季碳中心的苯并二氢呋喃衍生物。
• Domino Reaction for the Chemo- and Stereoselective Synthesis of <i>trans</i>-2,3-Dihydrobenzofurans from <i>N</i>-Thiophosphinyl Imines and Sulfur Ylides
  作者：Peizhong Xie、Liye Wang、Lihua Yang、Erqing Li、Jianze, Ma、You Huang、Ruyu Chen

  DOI：10.1021/jo2008737

  日期：2011.10.7

  A novel domino annulation between sulfur ylides and salicyl N-thiophosphinyl imines was developed. The method allows the synthesis of a highly substituted trans-2,3-dihydrobenzofuran skeleton with high yield and excellent chemo- and stereoselectivity.
• PPh₃-Catalyzed Domino Reaction: A Facile Method for the Synthesis of Chroman Derivatives
  作者：Xiangtai Meng、You Huang、Hongxia Zhao、Peizhong Xie、Jianze Ma、Ruyu Chen

  DOI：10.1021/ol802917d

  日期：2009.2.19

  A novel domino reaction catalyzed by triphenylphosphine was developed for synthesis of the highly functionalized chroman derivatives. The first example that the gamma-CH3 of allenoate undergoes cyclization to form chroman derivates was reported.