(2S)-2-[[(1S,2S)-2-diphenylphosphanylcyclohexyl]carbamothioylamino]-3,3-dimethyl-N,N-bis[(4-phenylphenyl)methyl]butanamide | 1023287-35-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S)-2-[[(1S,2S)-2-diphenylphosphanylcyclohexyl]carbamothioylamino]-3,3-dimethyl-N,N-bis[(4-phenylphenyl)methyl]butanamide
• CAS: 1023287-35-5
• 化学式: C₅₁H₅₄N₃OPS
• 分子量: 788.049
• InChiKey: XXAUVVMYTUOXAU-UTVRUGRBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.7
• 重原子数：
  57
• 可旋转键数：
  13
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  76.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  、 (1S,2S)-2-(二苯基膦)环己胺 以 二氯甲烷 为溶剂， 反应 24.0h， 以2.178 g的产率得到(2S)-2-[[(1S,2S)-2-diphenylphosphanylcyclohexyl]carbamothioylamino]-3,3-dimethyl-N,N-bis[(4-phenylphenyl)methyl]butanamide
  参考文献：
  名称：

  Cooperative, Highly Enantioselective Phosphinothiourea Catalysis of Imine−Allene [3 + 2] Cycloadditions

  摘要：

  A new family of phosphinthiourea catalysts was developed for the highly enantioselective synthesis of 2-aryl-2,5-hydropyrroles via a [3 + 2] cycloaddition of an electron-deficient allene with aryl and heteroaryl diphenylphosphinoylimines. The presence of both H(2)O and Et(3)N as additives was found to be important for achieving optimal rates. Dual activation of both nucleophile and electrophile by the bifunctional catalyst is invoked to account for the observed high reactivity and enantioselectivity.

  DOI：

  10.1021/ja801344w
• 作为试剂：
  描述：

  5,5-二甲基海因 、 乙基戊-2,3-二烯酸酯 在 (2S)-2-[[(1S,2S)-2-diphenylphosphanylcyclohexyl]carbamothioylamino]-3,3-dimethyl-N,N-bis[(4-phenylphenyl)methyl]butanamide 作用下， 以 甲苯 为溶剂， 以73%的产率得到
  参考文献：
  名称：

  Highly Enantioselective, Intermolecular Hydroamination of Allenyl Esters Catalyzed by Bifunctional Phosphinothioureas

  摘要：

  Bifunctional phosphinothiourea catalysts have been developed successfully for the highly regio- and enantioselective gamma-hydroamination of allenyl and propargyl esters with N-methoxy carbamate nucleophiles to yield alpha,beta-unsaturated gamma-amino acid ester products. In the case of propargyl ester substrates, the reaction proceeds through reversible phosphinothiourea-catalyzed isomerization to the corresponding allenyl ester. The high enantioselectivity of the process is attributed to a cooperative conjugate addition of a thiourea-bound carbamate anion to a vinyl phosphonium ion resulting from covalent activation of the allenyl ester substrate.

  DOI：

  10.1021/ja5117638

文献信息

• Cooperative, Highly Enantioselective Phosphinothiourea Catalysis of Imine−Allene [3 + 2] Cycloadditions
  作者：Yuan-Qing Fang、Eric N. Jacobsen

  DOI：10.1021/ja801344w

  日期：2008.4.1

  A new family of phosphinthiourea catalysts was developed for the highly enantioselective synthesis of 2-aryl-2,5-hydropyrroles via a [3 + 2] cycloaddition of an electron-deficient allene with aryl and heteroaryl diphenylphosphinoylimines. The presence of both H(2)O and Et(3)N as additives was found to be important for achieving optimal rates. Dual activation of both nucleophile and electrophile by the bifunctional catalyst is invoked to account for the observed high reactivity and enantioselectivity.