(+/-)-(4-bromophenyl)alanine ethyl ester hydrochloride | 100129-11-1

• 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: (+/-)-(4-bromophenyl)alanine ethyl ester hydrochloride
• 英文别名: Ethyl 2-amino-3-(4-bromophenyl)propanoate hydrochloride；ethyl 2-amino-3-(4-bromophenyl)propanoate;hydrochloride
• CAS: 100129-11-1
• 化学式: C₁₁H₁₄BrNO₂*ClH
• 分子量: 308.603
• InChiKey: ONNVTYWLAUCHJE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  52.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-(4-bromophenyl)alanine ethyl ester hydrochloride 在 metal N-甲基吗啉 、 sodium hydroxide 、 超重氢 、 三氟乙酸 作用下， 以 甲醇 为溶剂， 生成 Glycyl-p-tritylphenylalanine
  参考文献：
  名称：

  Chloramines VI:  Chlorination of Glycylphenylalanine in Model Solutions and in a Wastewater

  摘要：

  Model solutions of the dipeptide glycylphenylalanine were chlorinated at pH 7.0 to five different chlorine-to-peptide (Cl-2/peptide) mole ratios and analyzed after 30 min by high-performance liquid chromatography. At Cl-2/peptide mole ratios less than or equal to 1, N-chloroglycylphenylalanine (I) appears to be the only product. At mole ratios greater than or equal to 2, N,N-dichloroglycylphenylalanine (II) was the only product. II decomposes in model solutions (t(1/2) = 6.4 h) at pH 7.0 to form a compound tentatively identified as N-[2-(N'-chloroimino)ethanoyl]phenylalanine (III), an N-chloroaldimine. III, in turn, decomposes (t(1/2) = 36 h) to IV. From C-13- and H-1-NMR, GC/MS, and IR, IV was identified as N-cyanoacylphenylalanine. Glycyl-p-[H-3]-phenylalanine (VI) was synthesized in order to monitor the reaction at low concentrations of the compound in a wastewater. A secondary wastewater (TKN = 1.29 mg of N/L; [NH3]= 0.074 mg of N/L) was inoculated with VI and chlorinated to nine different chlorine concentrations. The stabilities of the tritiated analogs of II and III in the wastewater were comparable to those determined in model solutions.

  DOI：

  10.1021/es960794a
• 作为产物：
  描述：

  乙醇 、 对溴苯丙氨酸 在 盐酸 作用下， 生成 (+/-)-(4-bromophenyl)alanine ethyl ester hydrochloride
  参考文献：
  名称：

  Chloramines VI:  Chlorination of Glycylphenylalanine in Model Solutions and in a Wastewater

  摘要：

  Model solutions of the dipeptide glycylphenylalanine were chlorinated at pH 7.0 to five different chlorine-to-peptide (Cl-2/peptide) mole ratios and analyzed after 30 min by high-performance liquid chromatography. At Cl-2/peptide mole ratios less than or equal to 1, N-chloroglycylphenylalanine (I) appears to be the only product. At mole ratios greater than or equal to 2, N,N-dichloroglycylphenylalanine (II) was the only product. II decomposes in model solutions (t(1/2) = 6.4 h) at pH 7.0 to form a compound tentatively identified as N-[2-(N'-chloroimino)ethanoyl]phenylalanine (III), an N-chloroaldimine. III, in turn, decomposes (t(1/2) = 36 h) to IV. From C-13- and H-1-NMR, GC/MS, and IR, IV was identified as N-cyanoacylphenylalanine. Glycyl-p-[H-3]-phenylalanine (VI) was synthesized in order to monitor the reaction at low concentrations of the compound in a wastewater. A secondary wastewater (TKN = 1.29 mg of N/L; [NH3]= 0.074 mg of N/L) was inoculated with VI and chlorinated to nine different chlorine concentrations. The stabilities of the tritiated analogs of II and III in the wastewater were comparable to those determined in model solutions.

  DOI：

  10.1021/es960794a

文献信息

• Asymmetric catalytic alkynylation of thiazolones and azlactones for synthesis of quaternary α-amino acid precursors
  作者：Beibei Meng、Qian Shi、Yuan Meng、Jie Chen、Weiguo Cao、Xiaoyu Wu

  DOI：10.1039/d1ob00582k

  日期：——

  Asymmetric alkynylation of thiazolones and azlactones with alkynylbenziodoxolones as the electrophilic alkyne source catalyzed by thiourea phosphonium salt is described. By using thiazolones as nucleophiles, the desired alkyne functionalized thiazolones were obtained in 55–89% yields with 31–86% ee. Azlactones gave the desired products in comparable yields with lower enantioselectivities. Ring-opening

  描述了硫脲鏻盐催化的噻唑酮和吖内酯的不对称炔基化反应，其中炔基苯并氧唑酮作为亲电炔烃源。通过使用噻唑酮作为亲核试剂，以 55-89% 的产率和 31-86% 的 ee 获得所需的炔烃官能化噻唑酮。Azlactones 以较低的对映选择性以相当的产率得到所需的产物。炔基化产物的开环导致α，α-二取代的α-氨基酸衍生物有效而不会损失对映选择性。
• Bicyclic aromatic substituted pyridone derivative
  申请人：Sakuraba Shunji

  公开号：US20090264426A1

  公开（公告）日：2009-10-22

  Disclosed is a compound represented by the formula (I): Wherein R 1 and R 2 independently represent a hydrogen atom, a lower alkyl group or the like; X 1 , X 2 and X 3 independently represent a methine group or a nitrogen atom; Y 1 and Y 3 independently represent a single bond, —O— or the like; Y 2 represents a lower alkylene group or the like; W1 to W4 independently represent a single bond, a methylene group or the like; L represents a single bond, a methylene group or the like; Z 1 and Z 2 independently represent a single bond, a C 1-4 alkylene group or the like; Ar 1 represents an aromatic carbocyclic ring or the like; and Ar 2 represents a bicyclic aromatic carbocyclic ring or the like. The compound is useful as a pharmaceutical for a central disease, a cardiovascular disease or a metabolic disease.

  本发明揭示了一种化合物，其化学式为（I）：其中R1和R2分别代表氢原子、低碳烷基或类似物；X1、X2和X3分别代表亚甲基基团或氮原子；Y1和Y3分别代表单键、—O—或类似物；Y2代表低碳烷基基团或类似物；W1至W4独立地代表单键、亚甲基基团或类似物；L代表单键、亚甲基基团或类似物；Z1和Z2独立地代表单键、C1-4烷基基团或类似物；Ar1代表芳香环烷基环或类似物；Ar2代表双环芳香环烷基环或类似物。该化合物可用作治疗中枢疾病、心血管疾病或代谢性疾病的药物。
• WO2007/29847
  申请人：——

  公开号：——

  公开（公告）日：——
• Chloramines VII:  Chlorination of Alanylphenylalanine in Model Solutions and in a Wastewater
  作者：T. Christopher Fox、Daniel J. Keefe、Frank E. Scully、A. Laikhter

  DOI：10.1021/es9607953

  日期：1997.7.1

  Products of the 30-min chlorination of the dipeptide alanylphenylalanine were determined at pH 7.0 in model solutions. At Cl-2/peptide mole ratios less than or equal to 1, N-chloroalanylphenylalanine (I) is the only product. I is very stable at 23 degrees C (t(1/2) = 111 +/- 8.8 h). At mole ratios greater than or equal to 2, N,N-dichloroalanylphenylalanine (II) is the only product. II decomposes in model solutions (t(1/2) = 4.1 +/- 0.2 h) at pH 7.0 to form a compound identified as the N-chloroketimine N-[2-(N'-chloroimino)propanoyl]phenylalanine (III). The structure of III was identified by converting it to N-pyruvylphenylalanine tert-butyl ester by reduction, hydrolysis, and esterification and correlating the mass spectrum and GC retention time of this derivative with those of an authentic sample. III is unusually stable and decomposes slowly (t(1/2) = 125 +/- 6.5 h) to phenylalanine. In order to monitor the reactions of the dipeptide at low concentrations in a wastewater, alanyl-p-[H-3]-phenylalanine was synthesized. A primary wastewater (TKN = 19.82 mg/L; [NH3] = 19.79 mg/L) was inoculated with the radiolabeled dipeptide and chlorinated to seven different chlorine concentrations spanning the breakpoint curve of the wastewater. Products identical to those observed in model solutions were formed. The stabilities of the tritiated analogs of II and III in the wastewater were similar to those determined in model solutions. Time studies of the decomposition of N,N-dichloroalanyl-p-[H-3]-phenylalanine revealed the formation of an intermediate (A) not previously recognized. Modeling of the reactions of II suggested that A was a decomposition product of III in the formation of phenylalanine and was probably either an isocyanate or a carbamic acid formed from hydrolysis of an isocyanate intermediate.
• Chloramines VI:  Chlorination of Glycylphenylalanine in Model Solutions and in a Wastewater
  作者：Daniel J. Keefe、T. Christopher Fox、Barbara Conyers、Frank E. Scully

  DOI：10.1021/es960794a

  日期：1997.7.1

  Model solutions of the dipeptide glycylphenylalanine were chlorinated at pH 7.0 to five different chlorine-to-peptide (Cl-2/peptide) mole ratios and analyzed after 30 min by high-performance liquid chromatography. At Cl-2/peptide mole ratios less than or equal to 1, N-chloroglycylphenylalanine (I) appears to be the only product. At mole ratios greater than or equal to 2, N,N-dichloroglycylphenylalanine (II) was the only product. II decomposes in model solutions (t(1/2) = 6.4 h) at pH 7.0 to form a compound tentatively identified as N-[2-(N'-chloroimino)ethanoyl]phenylalanine (III), an N-chloroaldimine. III, in turn, decomposes (t(1/2) = 36 h) to IV. From C-13- and H-1-NMR, GC/MS, and IR, IV was identified as N-cyanoacylphenylalanine. Glycyl-p-[H-3]-phenylalanine (VI) was synthesized in order to monitor the reaction at low concentrations of the compound in a wastewater. A secondary wastewater (TKN = 1.29 mg of N/L; [NH3]= 0.074 mg of N/L) was inoculated with VI and chlorinated to nine different chlorine concentrations. The stabilities of the tritiated analogs of II and III in the wastewater were comparable to those determined in model solutions.