2',1':1,2:1'',2'':3,4-dibenzcyclohepta-1,3-diene-6-benzyloxycarbonylamino-6-carboxylic acid tert-butyl ester | 188975-97-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2',1':1,2:1'',2'':3,4-dibenzcyclohepta-1,3-diene-6-benzyloxycarbonylamino-6-carboxylic acid tert-butyl ester
• 英文别名: 2',1':1,2:1",2":3,4-dibenzcyclohepta-1,3-diene-6-benzyloxycarbonylamino-6-carboxylic acid tert-butyl ester
• CAS: 188975-97-5
• 化学式: C₂₈H₂₉NO₄
• 分子量: 443.543
• InChiKey: XKHOVILCDGZMOP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.46
• 重原子数：
  33.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  64.63
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2',1':1,2:1'',2'':3,4-dibenzcyclohepta-1,3-diene-6-benzyloxycarbonylamino-6-carboxylic acid tert-butyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以86.3%的产率得到2',1':1,2:1",2":3,4-dibenzcyclohepta-1,3-diene-6-benzyloxycarbonylamino-6-carboxylic acid
  参考文献：
  名称：

  Novel α,α-disubstituted α-aminoacids with axial dissymmetry and their N- or C-protected derivatives

  摘要：

  Racemic as well as enantiomerically pure 1,1'-binaphthyl-substituted alpha-aminoisobutyric acid (Bin), a new chiral atropoisomeric alpha, alpha-disubstituted glycine, and its biphenyl analogue (Bip), have been prepared with good yields by bis-alkylation of a glycine tert-butyl ester Schiff base with 2,2'-bis(bromomethyl)-1, 1'-binaphthyl and 2,2'-bis(bromomethyl)-1,1'-biphenyl, respectively, under phase transfer conditions. The free aminoacids Bin and Bip, as well as their N-protected (Z, Boc, Fmoc) and/or C-protected (ethyl or tert-butyl esters) derivatives, useful for the incorporation of these new aminoacids into peptides, have been obtained. A slow interconversion between the two enantiomers of the Bip derivatives is generally observed in H-1 NMR at room temperature, with a rotational energy barrier of 59 kJ mol(-1). (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00009-8
• 作为产物：
  描述：

  2,2′-双(溴甲基)-1,1′-联苯 在 氢氧化钾 、 盐酸羟胺 、 四丁基溴化铵 、 sodium acetate 、 potassium carbonate 作用下， 以 乙醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 120.0h， 生成 2',1':1,2:1'',2'':3,4-dibenzcyclohepta-1,3-diene-6-benzyloxycarbonylamino-6-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Novel α,α-disubstituted α-aminoacids with axial dissymmetry and their N- or C-protected derivatives

  摘要：

  Racemic as well as enantiomerically pure 1,1'-binaphthyl-substituted alpha-aminoisobutyric acid (Bin), a new chiral atropoisomeric alpha, alpha-disubstituted glycine, and its biphenyl analogue (Bip), have been prepared with good yields by bis-alkylation of a glycine tert-butyl ester Schiff base with 2,2'-bis(bromomethyl)-1, 1'-binaphthyl and 2,2'-bis(bromomethyl)-1,1'-biphenyl, respectively, under phase transfer conditions. The free aminoacids Bin and Bip, as well as their N-protected (Z, Boc, Fmoc) and/or C-protected (ethyl or tert-butyl esters) derivatives, useful for the incorporation of these new aminoacids into peptides, have been obtained. A slow interconversion between the two enantiomers of the Bip derivatives is generally observed in H-1 NMR at room temperature, with a rotational energy barrier of 59 kJ mol(-1). (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00009-8