2',1':1,2;1'',2'':3,4-dibenzocyclohepta-1,3-diene-6-amino-6-carboxylic acid ethyl ester | 188975-92-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2',1':1,2;1'',2'':3,4-dibenzocyclohepta-1,3-diene-6-amino-6-carboxylic acid ethyl ester
• 英文别名: 2',1':1,2;1'',2'':3,4-dibenzcyclohepta-1,3-diene-6-amino-6-carboxylic acid ethyl ester；Ethyl 6-amino-6,7-dihydro-5H-dibenzo[a,c]cycloheptene-6-carboxylate；ethyl 9-aminotricyclo[9.4.0.02,7]pentadeca-1(15),2,4,6,11,13-hexaene-9-carboxylate
• CAS: 188975-92-0
• 化学式: C₁₈H₁₉NO₂
• 分子量: 281.354
• InChiKey: RWACZYGEFBVQGU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2',1':1,2;1'',2'':3,4-dibenzocyclohepta-1,3-diene-6-amino-6-carboxylic acid ethyl ester 在 sodium hydroxide 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 51.0h， 生成 2',1':1,2:1",2":3,4-dibenzcyclohepta-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：

  2,2′-双(溴甲基)-1,1′-联苯 在 盐酸 、 氢氧化钾 、 四丁基溴化铵 、 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 17.0h， 生成 2',1':1,2;1'',2'':3,4-dibenzocyclohepta-1,3-diene-6-amino-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

文献信息

• The Bip Method, Based on the Induced Circular Dichroism of a Flexible Biphenyl Probe in Terminally Protected -Bip-Xaa*- Dipeptides, for Assignment of the Absolute Configuration of β-Amino Acids
  作者：Laurence Dutot、Karen Wright、Anne Gaucher、Michel Wakselman、Jean-Paul Mazaleyrat、Marta De Zotti、Cristina Peggion、Fernando Formaggio、Claudio Toniolo

  DOI：10.1021/ja800059d

  日期：2008.5.1

  An induced axial chirality of the biphenyl core of the Bip (2',1':1,2;1'',2'':3,4-dibenzcyclohepta-1,3-diene-6-amino-6-carboxylic acid) residue in the terminally protected dipeptides Boc-Bip-beta-Xaa*-OMe (beta-Xaa* = L-beta(3)-HAla, L-beta(3)-HVal, L-beta(3)-HLeu, L-beta(3)-HPro, trans-(1S,2S)-ACHC, trans-(1R,2R)-ACHC, trans-(1S,2S)-ACPC, trans-(1R,2R)-ACPC) resulted in an induced circular dichroism

  Bip 联苯核的诱导轴向手性 (2',1':1,2;1'',2'':3,4-dibenzcyclohepta-1,3-diene-6-amino-6-carb acid ) 末端保护的二肽 Boc-Bip-beta-Xaa*-OMe (beta-Xaa* = L-beta(3)-HAla, L-beta(3)-HVal, L-beta(3)-HLeu, L-beta(3)-HPro, trans-(1S,2S)-ACHC, trans-(1R,2R)-ACHC, trans-(1S,2S)-ACPC, trans-(1R,2R)-ACPC)在诱导圆二色性中，揭示了 Bip 方法在可靠和快速分配手性 β-氨基酸的绝对构型方面的有用性。值得注意的是，Bip 方法还应用于独特的自旋标记、环状、β-氨基酸顺式/反式-β-TOAC 和反式-POAC。特别是，这项研究允许分配后一种化合物的对映异构体的未知绝对构型。
• Kotha, Sambasivarao; Behera, Manoranjan, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2004, vol. 43, # 5, p. 922 - 926
  作者：Kotha, Sambasivarao、Behera, Manoranjan

  DOI：——

  日期：——
• Ethyl 6-acetylamino-6,7-dihydro-5<i>H</i>-dibenzo[<i>a</i>,<i>c</i>]cycloheptene-6-carboxylate
  作者：Lakshminarasimhan Damodharan、Nagarajarao Shamaladevi、Vasantha Pattabhi、Manoranjan Behera、Sambasivarao Kotha

  DOI：10.1107/s0108270102004687

  日期：2002.5.15

  The title compound, C20H21NO3, is a derivative of Aib (alpha-aminoisobutyric acid) and is cyclized at the C-alpha position by biphenyl rings. The seven-membered ring possesses C2 symmetry. The C-alpha cyclization causes the backbone to assume a helical conformation in the crystal structure. The packing of the molecules is stabilized by intermolecular C-H...O, C-H...pi and N-H...O hydrogen bonds.