(+)-(S)-2',1':1,2:1",2":3,4-dinaphthcyclohepta-1,3-diene-6-tert-butyloxycarbonylamino-6-carboxylic acid ethyl ester | 178065-14-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (+)-(S)-2',1':1,2:1",2":3,4-dinaphthcyclohepta-1,3-diene-6-tert-butyloxycarbonylamino-6-carboxylic acid ethyl ester
• CAS: 178065-14-0
• 化学式: C₃₁H₃₁NO₄
• 分子量: 481.591
• InChiKey: KCVHDHIVYHMVHB-UHFFFAOYSA-N

物化性质

• 沸点：
  670.2±54.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.59
• 重原子数：
  36.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• 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：

  (+)-(S)-2',1':1,2:1",2":3,4-dinaphthcyclohepta-1,3-diene-6-tert-butyloxycarbonylamino-6-carboxylic acid ethyl ester 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以96.4%的产率得到(S)-2',1':1,2;1'',2'':3,4-dinaphthcyclohepta-1,3-diene-6-tert-butyloxycarbonylamino-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：

  4-{[1-(4-Chloro-phenyl)-meth-(E)-ylidene]-amino}-4,5-dihydro-3H-cyclohepta[2,1-a;3,4-a']dinaphthalene-4-carboxylic acid ethyl ester 在 盐酸 作用下， 以 乙腈 为溶剂， 反应 53.0h， 生成 (+)-(S)-2',1':1,2:1",2":3,4-dinaphthcyclohepta-1,3-diene-6-tert-butyloxycarbonylamino-6-carboxylic acid ethyl 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