[(dimethylcarbamoyl)methyl]triphenylphosphonium chloride | 113204-09-4

• 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: [(dimethylcarbamoyl)methyl]triphenylphosphonium chloride
• 英文别名: [2-(dimethylamino)-2-oxoethyl]-triphenylphosphanium;chloride
• CAS: 113204-09-4
• 化学式: C₂₂H₂₃NOP*Cl
• 分子量: 383.857
• InChiKey: CMMAFNCGURLWJU-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.07
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  20.31
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  [(dimethylcarbamoyl)methyl]triphenylphosphonium chloride 在 sodium perchlorate 作用下， 以 丙酮 为溶剂， 反应 2.0h， 以86%的产率得到[2-(dimethylamino)-2-oxoethyl]-triphenylphosphanium;perchlorate
  参考文献：
  名称：

  Synthesis and structural characterization of gold-(I), -(III) and silver(I) complexes of the ylide ligand Ph₃PCHC(O)NMe₂. Crystal structure of [(AuPPh₃)₂{µ-C(PPh₃)C(O)NMe₂}]ClO₄

  摘要：

  The reaction between [AuCl(tht)] (tht = tetrahydrothiophene) and the ylide Ph3P = CHC(O)NMe2 gives [AuCl{CH(PPh3)C(O)NMe2}] 1, which reacts with chlorine to give [AuCl3{CH(PPh3)C(O)-NMe2}] 2 and with the same ylide and NaClO4 to form [Au{CH(PPh3)C(O)NMe2}2]ClO4 3. The analogous silver complex [Ag{CH(PPh3)C(O)NMe2}2]ClO4 4 is obtained by the reaction of AgClO4 with the ylide in molar ratio 1:2. The phosphonium salt [Ph3PCH2C(O)NMe2]ClO4 reacts with [Au(acac)(PPh3)] (acac = acetylacetonate) to give [Au{CH(PPh3)C(O)NMe2}(PPh3)]ClO4 5 or [(AuPPh3)2{mu-C(PPh3)C(O)NMe2}]ClO4 6 depending on the reaction conditions. The structure of 6 was confirmed by an X-ray diffraction study at -95-degrees-C [space group P1BAR, a = 11.572(3), b = 11.836(3), c = 21.627(7) angstrom, alpha = 78.29(2), beta = 87.19(2), gamma = 75.65(2)-degrees, R = 0.076]; the Au...Au bond length is 2.938(1) angstrom.

  DOI：

  10.1039/dt9910002579
• 作为产物：
  描述：

  三苯基膦 、 2-氯-N,N-二甲基乙酰胺 以 氯仿 为溶剂， 反应 3.0h， 以83%的产率得到[(dimethylcarbamoyl)methyl]triphenylphosphonium chloride
  参考文献：
  名称：

  Synthesis and structural characterization of gold-(I), -(III) and silver(I) complexes of the ylide ligand Ph₃PCHC(O)NMe₂. Crystal structure of [(AuPPh₃)₂{µ-C(PPh₃)C(O)NMe₂}]ClO₄

  摘要：

  The reaction between [AuCl(tht)] (tht = tetrahydrothiophene) and the ylide Ph3P = CHC(O)NMe2 gives [AuCl{CH(PPh3)C(O)NMe2}] 1, which reacts with chlorine to give [AuCl3{CH(PPh3)C(O)-NMe2}] 2 and with the same ylide and NaClO4 to form [Au{CH(PPh3)C(O)NMe2}2]ClO4 3. The analogous silver complex [Ag{CH(PPh3)C(O)NMe2}2]ClO4 4 is obtained by the reaction of AgClO4 with the ylide in molar ratio 1:2. The phosphonium salt [Ph3PCH2C(O)NMe2]ClO4 reacts with [Au(acac)(PPh3)] (acac = acetylacetonate) to give [Au{CH(PPh3)C(O)NMe2}(PPh3)]ClO4 5 or [(AuPPh3)2{mu-C(PPh3)C(O)NMe2}]ClO4 6 depending on the reaction conditions. The structure of 6 was confirmed by an X-ray diffraction study at -95-degrees-C [space group P1BAR, a = 11.572(3), b = 11.836(3), c = 21.627(7) angstrom, alpha = 78.29(2), beta = 87.19(2), gamma = 75.65(2)-degrees, R = 0.076]; the Au...Au bond length is 2.938(1) angstrom.

  DOI：

  10.1039/dt9910002579

文献信息

• Titanocene‐Catalyzed [2+2] Cycloaddition of Bisenones and Comparison with Photoredox Catalysis and Established Methods
  作者：Zhenhua Zhang、Julius B. Stückrath、Stefan Grimme、Andreas Gansäuer

  DOI：10.1002/anie.202102739

  日期：2021.6.21

  Cp2Ti(TFA) is a broadly applicable catalyst for the [2+2] cycloaddition of bisenones by inner-sphere electron transfer. The attractiveness of this mechanism is shown by comparison with outer-sphere ET methods. DFT calculations show that the reaction proceeds through a unique unfavorable 5-exo (the rate-determining step) and a favorable 4-exo cyclization.

  Cp 2 Ti(TFA) 是一种广泛适用的催化剂，可通过内球电子转移进行双烯酮的[2+2]环加成反应。通过与外层 ET 方法的比较，显示了该机制的吸引力。 DFT 计算表明，反应通过独特的不利的 5- exo （速率决定步骤）和有利的 4- exo环化进行。
• Dari, Abdelmjid; Christiaens, Leon E.; Renson, Marcel J., Heterocycles, 1992, vol. 34, # 9, p. 1737 - 1748
  作者：Dari, Abdelmjid、Christiaens, Leon E.、Renson, Marcel J.

  DOI：——

  日期：——
• Synthesis of a carbon-14 labelled version of benzofuran GR151004B
  作者：Alan H. Wadsworth、Heather A. Mitchell、Ian Fellows、Derek R. Sutherland

  DOI：10.1002/(sici)1099-1344(199609)38:9<863::aid-jlcr895>3.0.co;2-0

  日期：1996.9