2-[(1R,3R)-3-(2-carboxyphenyl)-5,10-dioxo-2-phenyl-1,3-dihydro-[1,2,4]diazaphospholo[1,2-b]phthalazin-1-yl]benzoic acid | 615538-61-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 2-[(1R,3R)-3-(2-carboxyphenyl)-5,10-dioxo-2-phenyl-1,3-dihydro-[1,2,4]diazaphospholo[1,2-b]phthalazin-1-yl]benzoic acid
• CAS: 615538-61-9
• 化学式: C₃₀H₂₁N₂O₆P
• 分子量: 536.48
• InChiKey: MABPOIMFPLUFES-VSGBNLITSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  39
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  115
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-[(1R,3R)-3-(2-carboxyphenyl)-5,10-dioxo-2-phenyl-1,3-dihydro-[1,2,4]diazaphospholo[1,2-b]phthalazin-1-yl]benzoic acid 在 4-二甲氨基吡啶 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 三乙胺 、 N,N-二异丙基乙胺 、 对甲苯磺酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 39.0h， 生成 (1R,3R)-2-phenyl-1,3-bis[2-[(4S)-4-propan-2-yl-4,5-dihydro-1,3-oxazol-2-yl]phenyl]-1,3-dihydro-[1,2,4]diazaphospholo[1,2-b]phthalazine-5,10-dione
  参考文献：
  名称：

  Resolved Chiral 3,4-Diazaphospholanes and Their Application to Catalytic Asymmetric Allylic Alkylation

  摘要：

  One-pot condensation of PhPH2, phthaloyl chloride, and the azine of 2-carboxybenzaldehyde (1) results in the new phosphine, rac-N,N'-phthaloyl-2,3-(2-carboxyphenyl)-phenyl-3,4-diazaphospholane (rac-2), in 88% yield. Resolution via selective crystallization of the diastereomeric alpha-methylbenzylamine salts followed by coupling with amino acids and other amines provides rapid access to new collections of chiral phosphines (3). Pd-catalyzed alkylation of 1,3-dimethylallyl acetate and 1,3-diphenylallyl acetate at room temperature in the presence of 3 exhibits enantioselectivities as high as 92% ee and 97% ee, respectively, with strong sensitivity to the nature of the amino acid appendages. The presence of PF6- salts profoundly affects both the yield and the selectivity of catalytic allylic alkylation.

  DOI：

  10.1021/ja036359f
• 作为产物：
  描述：

  2,2'-(azinodimethylidyne)bis-benzoic acid 、 邻苯二甲酰氯 、 苯基膦 生成 2-[(1S,3S)-3-(2-carboxyphenyl)-5,10-dioxo-2-phenyl-1,3-dihydro-[1,2,4]diazaphospholo[1,2-b]phthalazin-1-yl]benzoic acid 、 2-[(1R,3R)-3-(2-carboxyphenyl)-5,10-dioxo-2-phenyl-1,3-dihydro-[1,2,4]diazaphospholo[1,2-b]phthalazin-1-yl]benzoic acid
  参考文献：
  名称：

  Resolved Chiral 3,4-Diazaphospholanes and Their Application to Catalytic Asymmetric Allylic Alkylation

  摘要：

  One-pot condensation of PhPH2, phthaloyl chloride, and the azine of 2-carboxybenzaldehyde (1) results in the new phosphine, rac-N,N'-phthaloyl-2,3-(2-carboxyphenyl)-phenyl-3,4-diazaphospholane (rac-2), in 88% yield. Resolution via selective crystallization of the diastereomeric alpha-methylbenzylamine salts followed by coupling with amino acids and other amines provides rapid access to new collections of chiral phosphines (3). Pd-catalyzed alkylation of 1,3-dimethylallyl acetate and 1,3-diphenylallyl acetate at room temperature in the presence of 3 exhibits enantioselectivities as high as 92% ee and 97% ee, respectively, with strong sensitivity to the nature of the amino acid appendages. The presence of PF6- salts profoundly affects both the yield and the selectivity of catalytic allylic alkylation.

  DOI：

  10.1021/ja036359f
• 作为试剂：
  描述：

  1,3-二苯基-2-丙烯基乙酸酯 、 丙二酸二甲酯 在 bis(η3-allyl-μ-chloropalladium(II)) 、 2-[(1R,3R)-3-(2-carboxyphenyl)-5,10-dioxo-2-phenyl-1,3-dihydro-[1,2,4]diazaphospholo[1,2-b]phthalazin-1-yl]benzoic acid sodium hexaflorophosphate 、 sodium acetate 、 N,O-双三甲硅基乙酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 17.25h， 以50%的产率得到
  参考文献：
  名称：

  [EN] DIAZAPHOSPHACYCLES
  [FR] DIAZAPHOSPHACYCLES

  摘要：

  公开号：

  WO2005042546A3

文献信息

• US7507820B2
  申请人：——

  公开号：US7507820B2

  公开（公告）日：2009-03-24
• Resolved Chiral 3,4-Diazaphospholanes and Their Application to Catalytic Asymmetric Allylic Alkylation
  作者：Thomas P. Clark、Clark R. Landis

  DOI：10.1021/ja036359f

  日期：2003.10.1

  One-pot condensation of PhPH2, phthaloyl chloride, and the azine of 2-carboxybenzaldehyde (1) results in the new phosphine, rac-N,N'-phthaloyl-2,3-(2-carboxyphenyl)-phenyl-3,4-diazaphospholane (rac-2), in 88% yield. Resolution via selective crystallization of the diastereomeric alpha-methylbenzylamine salts followed by coupling with amino acids and other amines provides rapid access to new collections of chiral phosphines (3). Pd-catalyzed alkylation of 1,3-dimethylallyl acetate and 1,3-diphenylallyl acetate at room temperature in the presence of 3 exhibits enantioselectivities as high as 92% ee and 97% ee, respectively, with strong sensitivity to the nature of the amino acid appendages. The presence of PF6- salts profoundly affects both the yield and the selectivity of catalytic allylic alkylation.
• [EN] DIAZAPHOSPHACYCLES<br/>[FR] DIAZAPHOSPHACYCLES
  申请人：WISCONSIN ALUMNI RES FOUND

  公开号：WO2005042546A3

  公开（公告）日：2005-09-01