N-<2-amino>ethyl>-N-<2-amino>ethyl>-4-nitro-L-phenylalanine benzyl ester | 146432-48-6

• 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: N-<2-amino>ethyl>-N-<2-amino>ethyl>-4-nitro-L-phenylalanine benzyl ester
• 英文别名: benzyl (2S)-2-[2-[bis[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]amino]ethyl-[2-[bis(2-oxo-2-phenylmethoxyethyl)amino]ethyl]amino]-3-(4-nitrophenyl)propanoate
• CAS: 146432-48-6
• 化学式: C₅₀H₆₂N₄O₁₂
• 分子量: 911.062
• InChiKey: BTMLKKJJQVDIMG-QLKFWGTOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  66
• 可旋转键数：
  31
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  187
• 氢给体数：
  0
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  N-<2-amino>ethyl>-N-<2-amino>ethyl>-4-nitro-L-phenylalanine benzyl ester 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.67h， 以98%的产率得到N-<2-ethyl>-N-<2-amino>ethyl>-4-nitro-L-phenylalanine benzyl ester trihydrochloride
  参考文献：
  名称：

  Synthesis of enantiomerically pure diethylenetriaminepentaacetic acid analogs. L-Phenylalanine as the educt for substitution at the central acetic acid

  摘要：

  The enantiospecific synthesis of diethylenetriaminepentaacetic acid (DTPA) analogues from L-phenylalanine via a bis N-alkylation strategy is described. N-Alkylation of p-nitrophenylalanine benzyl ester (4) occurs readily with dibenzyl and di-tert-butyl [N-(bromoethyl)amino]diacetates 5a and 5b using a phosphate buffer/acetonitrile reaction medium. N,N-Dialkyl (2a,2b) and N-monoalkyl (3a, 3b) derivatives Of L-p-nitrophenylalanine thus are obtained directly in a single operation. Subjecting the monoalkylated material, N-(ethylamino) diacetic acid di-tert-butyl ester 3b, to a second alkylation with dibenzyl bromoethylaminediacetate 5a affords mixed pentaester 2c in which the terminal carboxyl groups are differentiated as benzyl esters at one end and tert-butyl at the other. Both complete and selective deprotections of the differentiated carboxyl groups in pentaesters 2a, 2b, and 2c are possible, allowing specific control of the carboxyl functionality at each terminus. The enantiomeric composition of monoalkyl amino acids 3a and 3b was evaluated by derivatizing with (+)-alpha-methylbenzyl isocyanate to afford the corresponding ureas. Analysis of the ureas by HPLC established the enantiomeric purity in each case as >99 %, thereby also establishing the enantiomeric purity of dialkyl compounds as >99 %. Pentaacid 2d readily forms an optically active metal chelate with yttrium(III) as a single diastereomer.

  DOI：

  10.1021/jo00057a030
• 作为产物：
  描述：

  2-[bis(benzyloxycarbonylmethyl)amino]ethyl bromide 、 N-<2-amino>ethyl>-4-nitro-L-phenylalanine benzyl ester 在 pH 8 phosphate buffer 作用下， 以 乙腈 为溶剂， 反应 42.0h， 以42%的产率得到N-<2-amino>ethyl>-N-<2-amino>ethyl>-4-nitro-L-phenylalanine benzyl ester
  参考文献：
  名称：

  Synthesis of enantiomerically pure diethylenetriaminepentaacetic acid analogs. L-Phenylalanine as the educt for substitution at the central acetic acid

  摘要：

  The enantiospecific synthesis of diethylenetriaminepentaacetic acid (DTPA) analogues from L-phenylalanine via a bis N-alkylation strategy is described. N-Alkylation of p-nitrophenylalanine benzyl ester (4) occurs readily with dibenzyl and di-tert-butyl [N-(bromoethyl)amino]diacetates 5a and 5b using a phosphate buffer/acetonitrile reaction medium. N,N-Dialkyl (2a,2b) and N-monoalkyl (3a, 3b) derivatives Of L-p-nitrophenylalanine thus are obtained directly in a single operation. Subjecting the monoalkylated material, N-(ethylamino) diacetic acid di-tert-butyl ester 3b, to a second alkylation with dibenzyl bromoethylaminediacetate 5a affords mixed pentaester 2c in which the terminal carboxyl groups are differentiated as benzyl esters at one end and tert-butyl at the other. Both complete and selective deprotections of the differentiated carboxyl groups in pentaesters 2a, 2b, and 2c are possible, allowing specific control of the carboxyl functionality at each terminus. The enantiomeric composition of monoalkyl amino acids 3a and 3b was evaluated by derivatizing with (+)-alpha-methylbenzyl isocyanate to afford the corresponding ureas. Analysis of the ureas by HPLC established the enantiomeric purity in each case as >99 %, thereby also establishing the enantiomeric purity of dialkyl compounds as >99 %. Pentaacid 2d readily forms an optically active metal chelate with yttrium(III) as a single diastereomer.

  DOI：

  10.1021/jo00057a030

文献信息

• Synthesis of enantiomerically pure diethylenetriaminepentaacetic acid analogs. L-Phenylalanine as the educt for substitution at the central acetic acid
  作者：Matthew A. Williams、Henry Rapoport

  DOI：10.1021/jo00057a030

  日期：1993.2

  The enantiospecific synthesis of diethylenetriaminepentaacetic acid (DTPA) analogues from L-phenylalanine via a bis N-alkylation strategy is described. N-Alkylation of p-nitrophenylalanine benzyl ester (4) occurs readily with dibenzyl and di-tert-butyl [N-(bromoethyl)amino]diacetates 5a and 5b using a phosphate buffer/acetonitrile reaction medium. N,N-Dialkyl (2a,2b) and N-monoalkyl (3a, 3b) derivatives Of L-p-nitrophenylalanine thus are obtained directly in a single operation. Subjecting the monoalkylated material, N-(ethylamino) diacetic acid di-tert-butyl ester 3b, to a second alkylation with dibenzyl bromoethylaminediacetate 5a affords mixed pentaester 2c in which the terminal carboxyl groups are differentiated as benzyl esters at one end and tert-butyl at the other. Both complete and selective deprotections of the differentiated carboxyl groups in pentaesters 2a, 2b, and 2c are possible, allowing specific control of the carboxyl functionality at each terminus. The enantiomeric composition of monoalkyl amino acids 3a and 3b was evaluated by derivatizing with (+)-alpha-methylbenzyl isocyanate to afford the corresponding ureas. Analysis of the ureas by HPLC established the enantiomeric purity in each case as >99 %, thereby also establishing the enantiomeric purity of dialkyl compounds as >99 %. Pentaacid 2d readily forms an optically active metal chelate with yttrium(III) as a single diastereomer.