methyl L-N-benzoyl(1,4-cyclohexadienyl)alaninate | 171898-36-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl L-N-benzoyl(1,4-cyclohexadienyl)alaninate
• 英文别名: methyl (S)-N-benzoyl-3-(1,4-cyclohexadien-1-yl)alaninate；methyl N-benzoyl(cyclohexa-1,4-dienyl)-L-alaninate；Methyl L-N-benzoyl-3-(cyclohexa-1,4-dienyl)alaninate；methyl (2S)-2-benzamido-3-cyclohexa-1,4-dien-1-ylpropanoate
• CAS: 171898-36-5
• 化学式: C₁₇H₁₉NO₃
• 分子量: 285.343
• InChiKey: QXFPEXFBEKIURJ-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl L-N-benzoyl(1,4-cyclohexadienyl)alaninate 在 二甲基硫 、 碳酸氢钠 、 臭氧 作用下， 生成 methyl (2S)-2-benzamido-4,6-dioxohexanoate
  参考文献：
  名称：

  Zvilichovsky, Gury; Gurvich, Vadim, Journal of the Chemical Society. Perkin transactions I, 1997, # 7, p. 1069 - 1071

  摘要：

  DOI：
• 作为产物：
  描述：

  2,5-二氢苯丙氨酸 在 sodium hydroxide 、 camphor-10-sulfonic acid 作用下， 反应 4.75h， 生成 methyl L-N-benzoyl(1,4-cyclohexadienyl)alaninate
  参考文献：
  名称：

  Ozonolysis of (cyclohexa-1,4-dienyl)-L-alanine. An approach to the synthesis of new unnatural amino acids. X-Ray molecular structure of 2-hydroxy-7-methyl-3-phenylpyrazolo[1,5-a]pyrimidine

  摘要：

  The aromatic ring in L-phenylalanine was transformed into isoxazolyl, N-phenylpyrazolyl, and the bicyclic pyrazolo[1,5-a]pyrimidinyl groups, by a combination of Birch reduction and ozonolysis, followed by condensation with the relevant binucleophiles. The ozonolysis was carried out on the N-acylated esters of cyclohexa-1,4-dienylalanine. The resulting N-acylated esters of heterocyclic alanine derivatives were obtained without isolation of the ozonolysis products. 4-Phenylpyrazolidine-3,5-dione was used as a 'hydrazine donor' in the construction of a pyrazolyl group, as direct condensation with hydrazine was successful.

  DOI：

  10.1039/p19950002509

文献信息

• Products of ozonolysis of L-1,4-cyclohexadienylalanine. Intramolecular cyclization and cyclization with hydroxylamine. The synthesis of two isomers of L-isoxazolylalanine
  作者：Gury Zvilichovsky、Vadim Gurvich

  DOI：10.1016/s0040-4020(97)00118-x

  日期：1997.3

  4-cyclohexadienylalanine followed by ozonolysis of the unsaturated ring. Intramolecular cyclization of the ozonolysis product occured upon treatment with acid. The cyclization of the product of ozonolysis with hydroxylamine was studied as well. The formation of both 5- and 3-isoxazolylalanine is demonstrated. Mechanism of formation of these products and structure of intermediates are discussed.

  将保护的L-苯丙氨酸还原为L-1,4-环己二烯基丙氨酸，然后进行不饱和环的臭氧分解。臭氧分解产物的分子内环化在用酸处理时发生。还研究了用羟胺对臭氧分解产物的环化。证实了5-和3-异恶唑基丙氨酸的形成。讨论了这些产物的形成机理和中间体的结构。
• Ozonolysis of 1,4-Cyclohexadienes in the Presence of Methanol and Acid. Mechanism and Intermediates in the Conversion of 1,4-Cyclohexadiene Derivatives to β-Keto Esters¹
  作者：Isra Gbara-Haj-Yahia、Gury Zvilichovsky、Noa Seri

  DOI：10.1021/jo049731y

  日期：2004.6.1

  preparation of β-keto esters directly from 1,4-cyclohexadiene derivatives are described. This procedure is a further step in the application of the synthetic methodology, which consists of the combination of Birch reduction of available benzene derivatives followed by ozonolysis. In this work, the syntheses of derivatives of dimethyl γ-keto-α-aminoadipate and dimethyl β-keto glutamate from the corresponding

  描述了直接由1，4-环己二烯衍生物制备β-酮酯的条件。该程序是合成方法应用的又一步，该方法包括将可用苯衍生物的桦木还原后进行臭氧分解的组合。在这项工作中，描述了由相应的1，4-环己二烯衍生物合成γ-酮-α-氨基己二酸二甲酯和β-酮谷氨酸二甲酯的衍生物。后者的化合物分别由苯丙氨酸和苯甘氨酸制备。在存在和不存在酸的情况下，在甲醇存在下对1,4-环己二烯的简单烷基衍生物进行臭氧分解的研究有助于建立该反应的机理。断裂的两个双键的接近度，导致中间体形成1,2-二氧戊环衍生物，可以通过NMR光谱法鉴定。结果表明，不管所形成的初级臭氧化物的裂解的区域选择性如何，所有的1,2-二氧戊环衍生物都可以生成β-酮酸酯。这是由于在甲醇和酸存在下这些二氧戊环之间的平衡。
• Ozonolysis of (cyclohexa-1,4-dienyl)-L-alanine. An approach to the synthesis of new unnatural amino acids. X-Ray molecular structure of 2-hydroxy-7-methyl-3-phenylpyrazolo[1,5-a]pyrimidine
  作者：Gury Zvilichovsky、Vadim Gurvich

  DOI：10.1039/p19950002509

  日期：——

  The aromatic ring in L-phenylalanine was transformed into isoxazolyl, N-phenylpyrazolyl, and the bicyclic pyrazolo[1,5-a]pyrimidinyl groups, by a combination of Birch reduction and ozonolysis, followed by condensation with the relevant binucleophiles. The ozonolysis was carried out on the N-acylated esters of cyclohexa-1,4-dienylalanine. The resulting N-acylated esters of heterocyclic alanine derivatives were obtained without isolation of the ozonolysis products. 4-Phenylpyrazolidine-3,5-dione was used as a 'hydrazine donor' in the construction of a pyrazolyl group, as direct condensation with hydrazine was successful.
• Zvilichovsky, Gury; Gurvich, Vadim, Journal of the Chemical Society. Perkin transactions I, 1997, # 7, p. 1069 - 1071
  作者：Zvilichovsky, Gury、Gurvich, Vadim

  DOI：——

  日期：——