4-[[Diphenylphosphanylmethyl(diphenyl)-lambda5-phosphanylidene]amino]-2,3,5,6-tetrafluorobenzamide | 215873-27-1

• 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: 4-[[Diphenylphosphanylmethyl(diphenyl)-lambda5-phosphanylidene]amino]-2,3,5,6-tetrafluorobenzamide
• 英文别名: 4-[[diphenylphosphanylmethyl(diphenyl)-λ5-phosphanylidene]amino]-2,3,5,6-tetrafluorobenzamide
• CAS: 215873-27-1
• 化学式: C₃₂H₂₄F₄N₂OP₂
• 分子量: 590.496
• InChiKey: ZGQRSUOZFOVVDI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  41
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.03
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  二(氰基苯)二氯化钯 、 4-[[Diphenylphosphanylmethyl(diphenyl)-lambda5-phosphanylidene]amino]-2,3,5,6-tetrafluorobenzamide 以 二氯甲烷 为溶剂， 以78.1%的产率得到dichloropalladium;4-[[diphenylphosphanylmethyl(diphenyl)-λ5-phosphanylidene]amino]-2,3,5,6-tetrafluorobenzamide
  参考文献：
  名称：

  Retention of Inhibitory Potency of an ACE Inhibitor Conjugated with Rh(III) and Pd(II) (Iminophosphorano)phosphines. Synthesis and X-ray Structural Investigations

  摘要：

  Succinimido, amido, and ester functionalized tetrafluoroaryl azides selectively oxidize bisdiphenylphosphinomethane at one of the P(III) centers giving (iminophosphorano)phosphines 6, 7, and 8 respectively in high yields. Succinimido functionalized perfluoroaryl azido (iminophosphorano)phosphine is attached to angiotensin converting enzyme (ACE) inhibitor, lisinopril at one end, leaving the other end for chelation to Rh(III) and Pd(II) precursors including radioactive analogues establishing the hetero-bifunctionality for potential in vivo tracking of the radiotracer. The measurement of inhibitory potency of lisinopril-metal conjugates (Rh and Pd), modified through the primary amine reveals an increase in inhibitory potency, although small, retaining the target potential of native lisinopril toward specific biological sites. However, direct complexation utilizing the carboxylic groups of lisinopril with a Cu precursor resulted in the reduction of inhibitory potency from nM to mu M levels rendering it less useful for applications as an ACE inhibitor. Single-crystal X-ray structural investigation of the Rh(III) perfluoroaryl (iminophosphorano)phosphine complex 12 shows a distorted mer octahedral configuration with two ligands per metal center and only one of the phosphiniminato nitrogen atom coordinating to the metal. Pd(II) complex 18 reveals that the metal is bound to the iminato nitrogen atom and the P(III) center via cis disposition to form a five-membered ring. X-ray data for 12: triclinic, P-l, 11.570 (6) Angstrom b = 13.668 Angstrom (7) c = 20.709 (10) Angstrom, alpha = 86.068 (10), beta = 83.774 (10), gamma = 83.503 (10) a = 3229.6 (3) Angstrom(3), Z= 2, R = 0.028, R-w, 0.050. X-ray data for 18: triclinic, P-1, a = 11.457 (3) Angstrom, b = 12.223 (3) Angstrom, c = 13.219 (4) Angstrom, alpha = 89.98 (20), beta = 73.710 (20), gamma = 69.980 (20), V = 1665.7 (8) Angstrom(3), Z = 2, R = 0.024, R-w = 0.031.

  DOI：

  10.1021/ja9802403
• 作为产物：
  描述：

  4-叠氮基-2,3,5,6-四氟苯甲酰胺 、 双二苯基膦甲烷 以 甲苯 为溶剂， 反应 3.0h， 以78.5%的产率得到4-[[Diphenylphosphanylmethyl(diphenyl)-lambda5-phosphanylidene]amino]-2,3,5,6-tetrafluorobenzamide
  参考文献：
  名称：

  Retention of Inhibitory Potency of an ACE Inhibitor Conjugated with Rh(III) and Pd(II) (Iminophosphorano)phosphines. Synthesis and X-ray Structural Investigations

  摘要：

  Succinimido, amido, and ester functionalized tetrafluoroaryl azides selectively oxidize bisdiphenylphosphinomethane at one of the P(III) centers giving (iminophosphorano)phosphines 6, 7, and 8 respectively in high yields. Succinimido functionalized perfluoroaryl azido (iminophosphorano)phosphine is attached to angiotensin converting enzyme (ACE) inhibitor, lisinopril at one end, leaving the other end for chelation to Rh(III) and Pd(II) precursors including radioactive analogues establishing the hetero-bifunctionality for potential in vivo tracking of the radiotracer. The measurement of inhibitory potency of lisinopril-metal conjugates (Rh and Pd), modified through the primary amine reveals an increase in inhibitory potency, although small, retaining the target potential of native lisinopril toward specific biological sites. However, direct complexation utilizing the carboxylic groups of lisinopril with a Cu precursor resulted in the reduction of inhibitory potency from nM to mu M levels rendering it less useful for applications as an ACE inhibitor. Single-crystal X-ray structural investigation of the Rh(III) perfluoroaryl (iminophosphorano)phosphine complex 12 shows a distorted mer octahedral configuration with two ligands per metal center and only one of the phosphiniminato nitrogen atom coordinating to the metal. Pd(II) complex 18 reveals that the metal is bound to the iminato nitrogen atom and the P(III) center via cis disposition to form a five-membered ring. X-ray data for 12: triclinic, P-l, 11.570 (6) Angstrom b = 13.668 Angstrom (7) c = 20.709 (10) Angstrom, alpha = 86.068 (10), beta = 83.774 (10), gamma = 83.503 (10) a = 3229.6 (3) Angstrom(3), Z= 2, R = 0.028, R-w, 0.050. X-ray data for 18: triclinic, P-1, a = 11.457 (3) Angstrom, b = 12.223 (3) Angstrom, c = 13.219 (4) Angstrom, alpha = 89.98 (20), beta = 73.710 (20), gamma = 69.980 (20), V = 1665.7 (8) Angstrom(3), Z = 2, R = 0.024, R-w = 0.031.

  DOI：

  10.1021/ja9802403

文献信息

• Retention of Inhibitory Potency of an ACE Inhibitor Conjugated with Rh(III) and Pd(II) (Iminophosphorano)phosphines. Synthesis and X-ray Structural Investigations
  作者：Raghoottama S. Pandurangi、Kattesh V. Katti、Loreen Stillwell、Charles L. Barnes

  DOI：10.1021/ja9802403

  日期：1998.11.1

  Succinimido, amido, and ester functionalized tetrafluoroaryl azides selectively oxidize bisdiphenylphosphinomethane at one of the P(III) centers giving (iminophosphorano)phosphines 6, 7, and 8 respectively in high yields. Succinimido functionalized perfluoroaryl azido (iminophosphorano)phosphine is attached to angiotensin converting enzyme (ACE) inhibitor, lisinopril at one end, leaving the other end for chelation to Rh(III) and Pd(II) precursors including radioactive analogues establishing the hetero-bifunctionality for potential in vivo tracking of the radiotracer. The measurement of inhibitory potency of lisinopril-metal conjugates (Rh and Pd), modified through the primary amine reveals an increase in inhibitory potency, although small, retaining the target potential of native lisinopril toward specific biological sites. However, direct complexation utilizing the carboxylic groups of lisinopril with a Cu precursor resulted in the reduction of inhibitory potency from nM to mu M levels rendering it less useful for applications as an ACE inhibitor. Single-crystal X-ray structural investigation of the Rh(III) perfluoroaryl (iminophosphorano)phosphine complex 12 shows a distorted mer octahedral configuration with two ligands per metal center and only one of the phosphiniminato nitrogen atom coordinating to the metal. Pd(II) complex 18 reveals that the metal is bound to the iminato nitrogen atom and the P(III) center via cis disposition to form a five-membered ring. X-ray data for 12: triclinic, P-l, 11.570 (6) Angstrom b = 13.668 Angstrom (7) c = 20.709 (10) Angstrom, alpha = 86.068 (10), beta = 83.774 (10), gamma = 83.503 (10) a = 3229.6 (3) Angstrom(3), Z= 2, R = 0.028, R-w, 0.050. X-ray data for 18: triclinic, P-1, a = 11.457 (3) Angstrom, b = 12.223 (3) Angstrom, c = 13.219 (4) Angstrom, alpha = 89.98 (20), beta = 73.710 (20), gamma = 69.980 (20), V = 1665.7 (8) Angstrom(3), Z = 2, R = 0.024, R-w = 0.031.