5-[(2-Hydroxy-6-tricyclo[9.4.0.03,8]pentadeca-1(15),3(8),4,6,11,13-hexaenyl)oxy]pentanoic acid | 1025831-03-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 二苯并环庚烯
• 英文名称: 5-[(2-Hydroxy-6-tricyclo[9.4.0.03,8]pentadeca-1(15),3(8),4,6,11,13-hexaenyl)oxy]pentanoic acid
• CAS: 1025831-03-1
• 化学式: C₂₀H₂₂O₄
• 分子量: 326.392
• InChiKey: SFXALPOVIPASOG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  芴甲氧羰酰胺 、 5-[(2-Hydroxy-6-tricyclo[9.4.0.03,8]pentadeca-1(15),3(8),4,6,11,13-hexaenyl)oxy]pentanoic acid 在 对甲苯磺酸 、 溶剂黄146 作用下， 反应 1.0h， 生成 5-<<(R,S)-5-(Fmoc-amino)-10,11-dihydrodibenzocyclohepten-2-yl>oxy>valeric acid
  参考文献：
  名称：

  Synthesis of 5-(((R,S)-5-((9-Fluorenylmethoxycarbonyl)amino)-10,11-dihydrodibenzo[a,d]cyclohepten-2-yl)oxy)valeric Acid (CHA) and 5-(((R,S)-5-((9-Fluorenylmethoxycarbonyl)amino)dibenzo[a,d]-cyclohepten-2-yl)oxy)valeric Acid (CHE) Handles for the Solid-Phase Synthesis of C-Terminal Peptide Amides under Mild Conditions

  摘要：

  Two novel handles for peptide amide preparation under mild conditions were developed for use in highly efficient solid-phase peptide synthesis. These handles, 5-{[(R,S)-5-[(9-fluorenylmethoxy-carbonyl)amino]-10,11-dihydrodibenzo[a,d]cyclohepten-2-yl]oxy}valeric acid (CHA) and 5-{[(R,S)-5-[(9-fluorenylmethoxycarbonyl)amino]dibenzo[a,d]cyclohepten-2-yl]oxy}valeric acid (CHE), were attached to the solid support and were used for syntheses of peptides having a C-terminal amide by the fluorenylmethoxycarbonyl strategy. The cleavability of CHA and CHE was determined and compared with the that commercially available amide handles. CHA and CHE handles can be rapidly cleaved from the polymer support without significant side reactions using lower acid concentrations than those required for conventional handles. As CHA can be easily synthesized in large amounts, it is suitable for peptide amide preparation for pharmaceuticals. As CHE can be cleaved at very low concentrations of acid, it is especially suitable for preparing side chain-protected peptide amides: Several brain-gut peptides having a C-terminal amide were synthesized in high yield and high purity with these novel handles.

  DOI：

  10.1021/jo00105a010
• 作为产物：
  描述：

  3-甲氧基苯乙酸 在 W-2 Raney Ni sodium hydroxide 、 sodium tetrahydroborate 、 三氯化铝 、 TEA 、 potassium tert-butylate 、 氢气 、 sodium acetate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 N,N-二甲基甲酰胺 、 异丙醇 、 苯 为溶剂， 25.0~245.0 ℃ 、392.24 kPa 条件下， 反应 61.41h， 生成 5-[(2-Hydroxy-6-tricyclo[9.4.0.03,8]pentadeca-1(15),3(8),4,6,11,13-hexaenyl)oxy]pentanoic acid
  参考文献：
  名称：

  Synthesis of 5-(((R,S)-5-((9-Fluorenylmethoxycarbonyl)amino)-10,11-dihydrodibenzo[a,d]cyclohepten-2-yl)oxy)valeric Acid (CHA) and 5-(((R,S)-5-((9-Fluorenylmethoxycarbonyl)amino)dibenzo[a,d]-cyclohepten-2-yl)oxy)valeric Acid (CHE) Handles for the Solid-Phase Synthesis of C-Terminal Peptide Amides under Mild Conditions

  摘要：

  Two novel handles for peptide amide preparation under mild conditions were developed for use in highly efficient solid-phase peptide synthesis. These handles, 5-{[(R,S)-5-[(9-fluorenylmethoxy-carbonyl)amino]-10,11-dihydrodibenzo[a,d]cyclohepten-2-yl]oxy}valeric acid (CHA) and 5-{[(R,S)-5-[(9-fluorenylmethoxycarbonyl)amino]dibenzo[a,d]cyclohepten-2-yl]oxy}valeric acid (CHE), were attached to the solid support and were used for syntheses of peptides having a C-terminal amide by the fluorenylmethoxycarbonyl strategy. The cleavability of CHA and CHE was determined and compared with the that commercially available amide handles. CHA and CHE handles can be rapidly cleaved from the polymer support without significant side reactions using lower acid concentrations than those required for conventional handles. As CHA can be easily synthesized in large amounts, it is suitable for peptide amide preparation for pharmaceuticals. As CHE can be cleaved at very low concentrations of acid, it is especially suitable for preparing side chain-protected peptide amides: Several brain-gut peptides having a C-terminal amide were synthesized in high yield and high purity with these novel handles.

  DOI：

  10.1021/jo00105a010

文献信息

• Synthesis of 5-(((R,S)-5-((9-Fluorenylmethoxycarbonyl)amino)-10,11-dihydrodibenzo[a,d]cyclohepten-2-yl)oxy)valeric Acid (CHA) and 5-(((R,S)-5-((9-Fluorenylmethoxycarbonyl)amino)dibenzo[a,d]-cyclohepten-2-yl)oxy)valeric Acid (CHE) Handles for the Solid-Phase Synthesis of C-Terminal Peptide Amides under Mild Conditions
  作者：Masaki Noda、Minoru Yamaguchi、Eiji Ando、Kenji Takeda、Kiyoshi Nokihara

  DOI：10.1021/jo00105a010

  日期：1994.12

  Two novel handles for peptide amide preparation under mild conditions were developed for use in highly efficient solid-phase peptide synthesis. These handles, 5-[(R,S)-5-[(9-fluorenylmethoxy-carbonyl)amino]-10,11-dihydrodibenzo[a,d]cyclohepten-2-yl]oxy}valeric acid (CHA) and 5-[(R,S)-5-[(9-fluorenylmethoxycarbonyl)amino]dibenzo[a,d]cyclohepten-2-yl]oxy}valeric acid (CHE), were attached to the solid support and were used for syntheses of peptides having a C-terminal amide by the fluorenylmethoxycarbonyl strategy. The cleavability of CHA and CHE was determined and compared with the that commercially available amide handles. CHA and CHE handles can be rapidly cleaved from the polymer support without significant side reactions using lower acid concentrations than those required for conventional handles. As CHA can be easily synthesized in large amounts, it is suitable for peptide amide preparation for pharmaceuticals. As CHE can be cleaved at very low concentrations of acid, it is especially suitable for preparing side chain-protected peptide amides: Several brain-gut peptides having a C-terminal amide were synthesized in high yield and high purity with these novel handles.