N,N-dibenzyl-L-tyrosine methyl ester

• 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,N-dibenzyl-L-tyrosine methyl ester
• 英文别名: (S)-2-dibenzylamino-3-(4-hydroxyphenyl)propionic acid methyl ester；methyl (2S)-2-(dibenzylamino)-3-(4-hydroxyphenyl)propanoate
• 化学式: C₂₄H₂₅NO₃
• 分子量: 375.467
• InChiKey: BFNSSQWDQAAEJR-QHCPKHFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N,N-dibenzyl-L-tyrosine methyl ester 、 4-碘代苯乙酮 在 copper(l) iodide 、 N,N-二甲基甘氨酸盐酸盐 caesium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 15.0h， 以96%的产率得到(S)-3-[4-(4-acetylphenoxy)phenyl]-2-dibenzylaminopropionic acid methyl ester
  参考文献：
  名称：

  Mild and Nonracemizing Conditions for Ullmann-type Diaryl Ether Formation between Aryl Iodides and Tyrosine Derivatives

  摘要：

  [GRAPHICS]CuI/N,N-dimethylglycine-catalyzed coupling reaction of L-tyrosine derivatives and L-phenylalanine-derived iodides in the presence of Cs2CO3 works at 90 degrees C to provide the corresponding diaryl ether. Partial racemization occurs when N-Boc- and N-Cbz-protected aromatic amino esters are used, while N-trityl-and N,N-dibenzyl-protected aromatic amino esters give rise to coupling products without loss of optical purity. Little racemization is also observed in cases of N-Boc- and N-Cbz- protected aromatic amino acids as substrates. But their reaction yields are moderate. On the basis of these studies, shorter protocols for assembling (S,S)-isodityrosine and K-13 are developed.

  DOI：

  10.1021/jo0606960

文献信息

• Aminoalcohol derivatives and their use as beta 3 adrenergic agonists
  申请人：Fujisawa Pharmaceutical Co. Ltd.

  公开号：US20020143034A1

  公开（公告）日：2002-10-03

  A compound of the formula (I): 1 wherein X 1 is bond or —OCH 2 —; X 2 is —(CH 2 ) n —, in which n is 1, 2 or 3; X 3 is bond, —O—, —S—, —OCH 2 —, or —NH—; R 1 is phenyl or pyridyl each of which may have one or two substituent(s) selected from the group consisting of hydroxy, halogen, etc.; R 2 is hydrogen, (lower)alkoxycarbonyl, etc.; R 3 is hydroxy(lower)alkyl; halo(lower)alkyl, etc.; R 4 is aryl or unsaturated heterocyclic group, each of which may have one or two substituent(s) selected from the group consisting of lower alkyl, hydroxy, carbamoyl, halogen, lower alkoxy, etc.; and a salt thereof which is useful as a medicament.

  该化合物的结构式如下：其中X1是化学键或—OCH2—；X2是—(CH2)n—，其中n为1、2或3；X3是化学键，—O—，—S—，—OCH2—或—NH—；R1是苯基或吡啶基，每个基上可能有一个或两个亚基，如羟基、卤素等；R2是氢、（低）烷氧羰基等；R3是羟基（低）烷基、卤代（低）烷基等；R4是芳基或不饱和杂环基，每个基上可能有一个或两个亚基，如低烷基、羟基、氨基甲酰基、卤素、低烷氧基等；以及其盐，可用作药物。
• AMINOALCOHOL DERIVATIVES AND THEIR USE AS BETA 3 ADRENERGIC AGONISTS
  申请人：FUJISAWA PHARMACEUTICAL CO., LTD.

  公开号：EP1140849A1

  公开（公告）日：2001-10-10
• [EN] AMINOALCOHOL DERIVATIVES AND THEIR USE AS BETA 3 ADRENERGIC AGONISTS<br/>[FR] AMINO-ALCOOLS ET LEUR UTILISATION COMME AGONISTES BETA-3 ADRENERGIQUES
  申请人：FUJISAWA PHARMACEUTICAL CO

  公开号：WO2000040560A1

  公开（公告）日：2000-07-13

  A compound of formula (I) wherein X1 is bond or -OCH2-; X2 is -(CH2)n-, in which n is 1, 2 or 3; X3 is bond, -O-, -S-, -OCH2-, or -NH-; R1 is phenyl or pyridyl each of which may have one or two substituent(s) selected from the group consisting of hydroxy, halogen, etc.; R2 is hydrogen, (lower)alkoxycarbonyl, etc.; R3 is hydroxy(lower)alkyl; halo(lower)alkyl, etc.; R4 is aryl or unsaturated heterocyclic group, each of which may have one or two substituent(s) selected from the group consisting of lower alkyl, hydroxy, carbamoyl, halogen, lower alkoxy, etc.; and a salt thereof which is useful as a medicament.
• Mild and Nonracemizing Conditions for Ullmann-type Diaryl Ether Formation between Aryl Iodides and Tyrosine Derivatives
  作者：Qian Cai、Gang He、Dawei Ma

  DOI：10.1021/jo0606960

  日期：2006.7.1

  [GRAPHICS]CuI/N,N-dimethylglycine-catalyzed coupling reaction of L-tyrosine derivatives and L-phenylalanine-derived iodides in the presence of Cs2CO3 works at 90 degrees C to provide the corresponding diaryl ether. Partial racemization occurs when N-Boc- and N-Cbz-protected aromatic amino esters are used, while N-trityl-and N,N-dibenzyl-protected aromatic amino esters give rise to coupling products without loss of optical purity. Little racemization is also observed in cases of N-Boc- and N-Cbz- protected aromatic amino acids as substrates. But their reaction yields are moderate. On the basis of these studies, shorter protocols for assembling (S,S)-isodityrosine and K-13 are developed.