2-(benzylseleno)ethanoic acid | 19188-12-6

• 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: 2-(benzylseleno)ethanoic acid
• 英文别名: 2-benzylselenoethanoic acid；benzylselanyl-acetic acid；Benzylselanyl-essigsaeure；Benzylseleno-essigsaeure；2-(Benzylseleno)essigsaeure；(Benzylseleno)-essigsaeure；2-Benzylselanylacetic acid
• CAS: 19188-12-6
• 化学式: C₉H₁₀O₂Se
• 分子量: 229.137
• InChiKey: YBYURXIWCKLWFL-UHFFFAOYSA-N

物化性质

• 熔点：
  71 °C
• 沸点：
  365.8±35.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.39
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(benzylseleno)ethanoic acid 在 N-氯代丁二酰亚胺 、 偶氮二异丁腈 、 三乙胺 、 三氯氧磷 作用下， 以 四氯化碳 、 苯 为溶剂， 生成 cis-1-(4'-methoxyphenyl)-3-chloro-3-benzylseleno-4-phenylazetidin-2-one
  参考文献：
  名称：

  Seleno-β-lactams: synthesis of monocyclic and spirocyclic selenoazetidin-2-ones

  摘要：

  An efficient protocol for the synthesis of novel seleno-beta-lactams using operationally simple strategies is presented. 3-Phenyl/benzylseleno-beta-lactams, obtained from 2-phenyl/benzylselenoethanoic acids, are transformed to cis-3-chloro-3-phenyl/benzylseleno-beta-lactams, which undergo reaction with various active aliphatic and aromatic substrates catalyzed by Lewis acid to produce cis-3-alkoxy-3-phenyl/ benzylseleno-beta-lactams and C-3 monosubstituted seleno-beta-lactams. Halogen mediated intraselenyl cyclization of cis-3-(prop-2-ynyloxy)3-benzylseleno-beta-lactams affords novel spiro seleno-beta-lactams. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.02.001
• 作为产物：
  描述：

  hydroseleno-acetic acid ; mercury salt 在 sodium sulfide 、 sodium hydroxide 作用下， 生成 2-(benzylseleno)ethanoic acid
  参考文献：
  名称：

  Fredga, Svensk Kemisk Tidskrift, 1936, vol. 48, p. 92,93,96

  摘要：

  DOI：

文献信息

• Convenient Preparation of Benzylseleno‐ and Phenylselenoalkanoic Acids: Reagents for Synthesis of Organoselenium Compounds
  作者：Aman Bhalla、Sitansh Sharma、Kuldip K. Bhasin、Shamsher S. Bari

  DOI：10.1080/00397910601133540

  日期：2007.3

  Abstract An efficient and operationally simple route to benzylseleno‐ and phenylselenoalkanoic acids from ethyl benzyl/phenylselenoalkanoates is described. This involves preparation of ethyl benzyl/phenylselenoalkanoates as substrates by reaction of dibenzyl/diphenyl diselenide and sodium borohydride with ethyl chloroalkanoates in ethanol followed by basic hydrolysis and subsequent acidification.

  摘要描述了一种从苄基/苯基硒代链烷酸酯中制备苄基硒代和苯基硒代链烷酸的有效且操作简单的路线。这涉及通过二苄基/二苯基二硒化物和硼氢化钠与氯代链烷酸乙酯在乙醇中反应，然后进行碱性水解和随后的酸化来制备乙基苄基/苯基硒代链烷酸酯作为底物。
• Stereoselective synthesis of <i>trans</i>-benzo[<i>d</i>]oxazolyl)phenyl substituted β-lactams decorated with C-3 thio/seleno rich motifs: synthetic intermediates for diverse heterocycles
  作者：Preety Saini、Shalu Thakur、Ankita Garg、S. S. Bari、Aman Bhalla

  DOI：10.1080/17415993.2023.2206968

  日期：2023.9.3

  values of C3-H and C4-H (J = 1.4 to 2.6; C3-H and C4-H). The structure elucidation of all the thio/seleno anchored β-lactams 7a-i was performed using various spectroscopic techniques viz. FT-IR, NMR (1H, 13C, and 13C DEPT–135), 2D-NMR (1H–1H COSY and 1H–13C HSQC), elemental analysis (CHN), and mass spectrometry (ESI-MS). Further, divergent substrate scope accompanied by plausible mechanistic investigation

  在此，我们报告了立体选择性合成新型 C-3 硫代/硒代取代的邻位、间位和对位（2-苯并[ d ]恶唑基）苯基-β-内酰胺7a-i的有效方案。该反应通过利用不同的S/Se-烷基/芳基取代的酸6a-d和异构的邻-、间-和对-(2-苯并[ d ]恶唑基)苯基席夫碱3a-c进行，并独家形成反式-β-内酰胺。反式构型是根据 C 3的耦合常数值指定的-H和C 4 -H( J＝1.4至2.6；C3- H和C4- H )。所有硫代/硒基锚定的 β-内酰胺7a-i的结构阐明是使用各种光谱技术进行的。FT-IR、NMR（1 H、13 C 和13 C DEPT–135）、2D-NMR（1 H– 1 H COSY 和1 H– 13C HSQC）、元素分析（CHN）和质谱（ESI-MS）。此外，还描述了不同的底物范围以及合理的机制研究。立体选择性、良好的官能团耐受性和优异的产率以及更广泛的合成实用性赋予了本方案优势。
• Fredga,A., Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1974, vol. B28, # 6, p. 692 - 694
  作者：Fredga,A.

  DOI：——

  日期：——
• Synthesis and characterization of novel trans-3-benzyl/(diphenyl)methyl/naphthyl seleno substituted monocyclic β-lactams: X-ray structure of trans-1-(4′-methoxyphenyl)-3-(diphenyl)methylseleno-4-(4′-methoxyphenyl)azetidin-2-one
  作者：S.S. Bari、Aman Bhalla、Yogesh Nagpal、S.K. Mehta、K.K. Bhasin

  DOI：10.1016/j.jorganchem.2010.05.005

  日期：2010.8

  Several novel trans-3-benzyl/(diphenyl) methyl/naphthylseleno substituted monocyclic beta-lactams (5-7) have been synthesized in high yields. The reaction scheme inolves [2 + 2] cycloaddition (Staudinger) reaction between suitably substituted imines 4(a-h) and ketenes (B) accessed from 2-benzyl/(diphenyl) methyl/naphthylselenoethanoic acids (1-3) using POCl3 and triethylamine in refluxing toluene. Characterization of these newly synthesized seleno substituted beta-lactams has been performed by various spectroscopic techniques viz. NMR (H-1, C-13 and Se-77), FTIR, mass spectrometry and elemental analysis. The molecular structure of trans-1-(4'-methoxyphenyl)-3-(diphenyl) methylseleno-4-(4'-methoxyphenyl) azetidin-2-one (6b) has also been established with the help of single crystal X-ray analysis. (C) 2010 Elsevier B.V. All rights reserved.