N-(tert-Butyloxycarbonyl)-O-(2-oxopropyl)-L-tyrosine methyl ester | 170124-00-2

• 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-(tert-Butyloxycarbonyl)-O-(2-oxopropyl)-L-tyrosine methyl ester
• 英文别名: methyl (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-[4-(2-oxopropoxy)phenyl]propanoate
• CAS: 170124-00-2
• 化学式: C₁₈H₂₅NO₆
• 分子量: 351.4
• InChiKey: IDWSZCOQRIUMSR-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  90.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(tert-Butyloxycarbonyl)-O-(2-oxopropyl)-L-tyrosine methyl ester 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 24.0h， 生成 N-(tert-Butyloxycarbonyl)-O-<1-(butylthio)-3-oxo-1-buten-2-yl>-L-tyrosine methyl ester
  参考文献：
  名称：

  Synthesis of Functionalized Aryloxy 1,3-Butadienes and Their Transformation to Diaryl Ethers via Diels-Alder Cycloaddition Reactions

  摘要：

  The Diels-Alder reaction involving cycloaddition of aryloxy-substituted 1,3-butadienes with appropriate acetylenic electrophiles, followed by aromatization of the newly formed cyclohexadiene ring, has been used for the synthesis of diaryl ethers. The functionalized aryloxy 1,3-butadienes employed in this study were prepared by either of two methods: (1) methylenation of aryl esters via the Tebbe or related reagents, and (2) from 1-(aryloxy)-2-propanone by a sequence of formylation or alkylthio methlylenation, and subsequent enolsilylation. A tetrasubstituted butadiene containing two phenoxy groups at the 1 and 3 positions also was prepared by the latter method. The cycloaddition reactions of 2,3-dioxy-substituted dienes occurred in high yield, but, as expected, with no regioselectivity to furnish nearly equal mixtures of regioisomeric cycloadducts. In contrast, application of 1,2,3-trihetero-substituted dienes resulted in regiospecific cycloaddition reactions. Transformation of the cyclohexadiene cycloadducts to an aromatic ring was accomplished by dehydrogenation with DDQ or by elimination during the cycloaddition process of a molecule of an alkyl mercaptan. A chiral acetylenic ketone derived from D- or L-serine underwent condensation, without racemization, with aryloxy dienes to provide diaryl ethers related to the isodityrosine antibiotics.

  DOI：

  10.1021/jo00124a010
• 作为产物：
  描述：

  Boc-L-酪氨酸甲酯 、 溴丙酮 在 potassium carbonate 、 potassium iodide 作用下， 以 丙酮 为溶剂， 以100%的产率得到N-(tert-Butyloxycarbonyl)-O-(2-oxopropyl)-L-tyrosine methyl ester
  参考文献：
  名称：

  Radiolytic one-electron reduction characteristics of tyrosine derivative caged by 2-oxopropyl group

  摘要：

  We employed X-irradiation to activate a caged amino acid with a 2-oxoalkyl group. We designed and synthesized tyrosine derivative caged by a 2-oxoalkyl group (Tyr(Oxo)) to evaluate its radiolytic one-electron reduction characteristics in aqueous solution. Upon hypoxic X-irradiation, Tyr(Oxo) released a 2-oxopropyl group to form the corresponding uncaged tyrosine. In addition, radiolysis of dipeptides containing Tyr(Oxo) revealed that the efficiency of radiolytic removal of 2-oxopropyl group increased significantly by the presence of neighboring aromatic amino acids. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.10.018