N,N'-di-(1-naphthylmethylene)-1,2-cyclohexyldiamino N-phosphonylchloride | 1531629-95-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N,N'-di-(1-naphthylmethylene)-1,2-cyclohexyldiamino N-phosphonylchloride
• 英文别名: (3aR,7aR)-2-chloro-1,3-bis(naphthalen-1-ylmethyl)-3a,4,5,6,7,7a-hexahydrobenzo[d][1,3,2]diazaphosphole 2-oxide
• CAS: 1531629-95-4
• 化学式: C₂₈H₂₈ClN₂OP
• 分子量: 474.97
• InChiKey: SEPXJPDVOCQQTI-VSGBNLITSA-N

物化性质

• 沸点：
  653.9±58.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  33
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N,N'-di-(1-naphthylmethylene)-1,2-cyclohexyldiamino N-phosphonylchloride 、 甘氨酸甲酯盐酸盐 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以92%的产率得到methyl 2-[[(3aR,7aR)-1,3-bis(naphthalen-1-ylmethyl)-2-oxido-3a,4,5,6,7,7a-hexahydrobenzo[d][1,3,2]diazaphosphol-2-ium-2-yl]amino]acetate
  参考文献：
  名称：

  Group-Assisted Purification (GAP) for Protection of Amino Acids Using N-Phosphonyl Functional Groups

  摘要：

  Various phosphonyl halides have been synthesized and utilized as protection groups for amino acids. The protection synthesis was performed via GAP (Group-Assisted Purification) procedure under convenient conditions without the use of column chromatography and recrystallization. The synthesis can be carried out on applicational scales with excellent yields (82% - 98%). The phosphonyl protection of amino acids would provide a new greener tool for GAP peptide synthesis.

  DOI：

  10.3987/com-14-s(k)25
• 作为产物：
  描述：

  (1R,2R)-N,N'-bis[(1-naphthyl)-methyl]-1,2-diaminocyclohexane 在 三乙胺 、 三氯氧磷 作用下， 以 甲苯 为溶剂， 生成 N,N'-di-(1-naphthylmethylene)-1,2-cyclohexyldiamino N-phosphonylchloride
  参考文献：
  名称：

  Group-Assisted Purification (GAP) for Protection of Amino Acids Using N-Phosphonyl Functional Groups

  摘要：

  Various phosphonyl halides have been synthesized and utilized as protection groups for amino acids. The protection synthesis was performed via GAP (Group-Assisted Purification) procedure under convenient conditions without the use of column chromatography and recrystallization. The synthesis can be carried out on applicational scales with excellent yields (82% - 98%). The phosphonyl protection of amino acids would provide a new greener tool for GAP peptide synthesis.

  DOI：

  10.3987/com-14-s(k)25

文献信息

• Solution-phase-peptide synthesis via the group-assisted purification (GAP) chemistry without using chromatography and recrystallization
  作者：Jianbin Wu、Guanghui An、Siqi Lin、Jianbo Xie、Wei Zhou、Hao Sun、Yi Pan、Guigen Li

  DOI：10.1039/c3cc48509a

  日期：——

  The solution phase synthesis of N-protected amino acids and peptides has been achieved through GAP chemistry by avoiding disadvantages of the solid-phase-peptide synthesis (SPPS) and liquid-phase-peptide synthesis. The environmentally friendly GAP synthesis can substantially reduce the use of solvents, silica gels, energy and manpower.

  通过GAP化学方法，已实现了对N-保护氨基酸和肽的溶液相合成，避免了固相肽合成（SPPS）和液相肽合成的缺点。环保的GAP合成可以大幅减少溶剂、硅胶、能源和人力的使用。
• [EN] GROUP-ASSISTANT-PURIFICATION (GAP) SYNTHESIS OF VELCADE, DIMERIC ANALOGS, AND AMINO COMPOUNDS<br/>[FR] SYNTHÈSE GAP DE VELCADE, ANALOGUES DIMÈRES ET COMPOSÉS AMINÉS
  申请人：UNIV NANJING

  公开号：WO2014093723A2

  公开（公告）日：2014-06-19
• Group-Assisted Purification (GAP) for Protection of Amino Acids Using N-Phosphonyl Functional Groups
  作者：Guigen Li、Guanghui An、Cole Seifert、Hao Sun、Yi Pan

  DOI：10.3987/com-14-s(k)25

  日期：——

  Various phosphonyl halides have been synthesized and utilized as protection groups for amino acids. The protection synthesis was performed via GAP (Group-Assisted Purification) procedure under convenient conditions without the use of column chromatography and recrystallization. The synthesis can be carried out on applicational scales with excellent yields (82% - 98%). The phosphonyl protection of amino acids would provide a new greener tool for GAP peptide synthesis.