[1-14C]acetyl chloride | 676-77-7

• 分子结构分类: 有机化合物 - 有机盐 - 有机金属盐
• 英文名称: [1-14C]acetyl chloride
• 英文别名: Acetyl chloride,[1-14c]；acetyl chloride
• CAS: 676-77-7
• 化学式: C₂H₃ClO
• 分子量: 80.4872
• InChiKey: WETWJCDKMRHUPV-HQMMCQRPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  4
• 可旋转键数：
  0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  [1-14C]acetyl chloride 在 sodium azide 作用下， 以 苯 为溶剂， 反应 3.5h， 生成 [¹⁴C]isocyanato-methane
  参考文献：
  名称：

  Synthesis of high specific activity [14CO] methyl isocyanate and its use in the preparation of [14CO] eserine, [14CO] carbaryl and [14CO] IPMU

  摘要：

  DOI：

  10.1002/(sici)1099-1344(199805)41:5<387::aid-jlcr92>3.0.co;2-s
• 作为产物：
  描述：

  乙酸钠-1-14C 在 邻苯二甲酰氯 作用下， 反应 3.0h， 以100%的产率得到[1-14C]acetyl chloride
  参考文献：
  名称：

  阿托伐他汀，一种 HMG-COA 还原酶抑制剂和有效的脂质调节剂。第二部分。侧链标记的[14C]阿托伐他汀的合成

  摘要：

  [14C]阿托伐他汀以10步顺序合成，总产率为5.7%。标记物以 [1-14C] 乙酸钠形式引入，通过酰氯转化为 (S)-2-羟基-1,2,2-三苯乙酯 4。4 与醛 5 的手性缩合得到手性酯中间体6，产率约70%。在 6 酯交换为甲酯并与硫代乙酸锂叔丁酯缩合得到 (R)-β-酮酯 8 后，通过还原羟基酮 3 生成第二个手性中心，得到 (R,R)-二羟基酯 9然后通过酸将其转化为内酯11。在结晶过程中从母液中获得的所需纯非对映异构体11然后转化为相应的钙盐(2:1)13(阿托伐他汀)。版权所有 © 1999 John Wiley & Sons, Ltd.

  DOI：

  10.1002/(sici)1099-1344(199902)42:2<129::aid-jlcr174>3.0.co;2-o

文献信息

• A Light-Activated Antibody Catalyst
  作者：Matthew J. Taylor、Timothy Z. Hoffman、Jari T. Yli-Kauhaluoma、Richard A. Lerner、Kim D. Janda

  DOI：10.1021/ja982711r

  日期：1998.12.1

  per antibody) occurred. The singular product obtained in the antibody-catalyzed reaction was not observed in the uncatalyzed reaction unless the pH was lowered below 4. Studies suggested that the interplay of conformational control and chemical catalysis were responsible for the high specificity. A change in protonation state of the antibody was correlated with the inclusion of a new reaction pathway

  研究了用于多步 Norrish II 型光化学反应的催化抗体。α-酮酰胺底物 1b 吸收光能产生高能双自由基中间体，然后由抗体微环境引导形成四氢吡嗪 13，在 280 nm 照射下 kcat 为 1.4 × 10-3 min-1，对映体过量78%。用放射性标记底物进行的抗体催化反应表明几乎没有发生自我失活（每个抗体四次转换后 6.8 mol% 的共价修饰）。在未催化反应中观察不到在抗体催化反应中获得的单一产物，除非 pH 值低于 4。研究表明，构象控制和化学催化的相互作用是造成高特异性的原因。
• 10th international symposium on the synthesis and applications of isotopes and isotopically labelled compounds-applications of isotopes in pharmacology, clinical and medical research Session 16, Wednesday, June 17, 2009
  作者：Chad Elmore、Brad Maxwell

  DOI：10.1002/jlcr.1771

  日期：——

  Diverse topics, with a central theme are discussed. On the one hand, the preparation of an anti-epidermal growth factor MAB, labelled with 177Lu is detailed. In addition, traditional syntheses of isotopically labelled small molecules are also highlighted. Copyright © 2010 John Wiley & Sons, Ltd.

  围绕一个中心主题，讨论了各种不同的话题。一方面，详细介绍了用 177Lu 标记的抗表皮生长因子 MAB 的制备。此外，还重点介绍了同位素标记小分子的传统合成方法。Copyright © 2010 John Wiley & Sons, Ltd. All Rights Reserved.
• 10th international symposium on the synthesis and applications of isotopes and isotopically labelled compounds - poster presentations Session 19, Sunday, June 14 to Thursday, June 18, 2009
  作者：William Wheeler

  DOI：10.1002/jlcr.1776

  日期：——

  The poster session is a series of papers dealing with a conglomeration of all of the previous sessions. Cristian Postolache, the fourth of the Wiley Young Scientist Award winners gave a Poster in this session. Copyright © 2010 John Wiley & Sons, Ltd.

  海报展示环节由一系列论文组成，涵盖了之前所有环节的内容。第四位威利青年科学家奖获得者克里斯蒂安-波斯托拉奇（Cristian Postolache）在此环节发表了一篇海报。Copyright © 2010 John Wiley & Sons, Ltd. 版权所有。
• The synthesis of [¹⁴ C]4-acetylphenylalanine, effect on cell viability, and assessment of protein incorporation in male rat hepatocytes
  作者：Brad D. Maxwell、Van Ly、Barry Brock、Robert Dodge、Mark Tirmenstein、Jacqueline Calvano

  DOI：10.1002/jlcr.3499

  日期：2017.6.30

  PEGylation is a proven approach to prolonging the duration of action and enhancing biophysical solubility and stability of peptides. 4-Acetylphenylalanine is a novel amino acid with a ketone side chain that is uniquely reactive in proteins. The ketone functionality can react with an aminooxy functionalized polyethyleneglycol polymer to form a stable oxime adduct of the protein. One concern with using unnatural amino acids, such as 4-acetylphenylalanine, is the possibility of it being cleaved from the peptide and becoming incorporated into endogenous proteins. To determine whether this occurs, an in vitro experiment to assess the cell viability and amino acid incorporation into endogenous proteins using primary male rat hepatocytes in the presence of [14C]4-acetylphenylalanine, 4 or [14C(U)]L-phenylalanine was conducted. [14C]4-acetylphenylalanine, 4 was prepared in 2 radiochemical steps from [1-14C]acetyl chloride in an overall 8% radiochemical yield and in 99.9% radiochemical purity. The results showed that there was no evidence of carbon-14 incorporation into hepatocyte endogenous proteins with [14C]pAcF and there was no difference between it and L-phenylalanine in cell viability assessments at any of the concentrations studied between 0.1 and 1000 μM.

  聚乙二醇化是一种行之有效的方法，可延长多肽的作用时间，提高其生物物理溶解度和稳定性。4-乙酰基苯丙氨酸是一种新型氨基酸，具有酮侧链，在蛋白质中具有独特的反应性。酮官能团可与氨基氧官能化的聚乙二醇聚合物反应，形成稳定的蛋白质肟加合物。使用非天然氨基酸（如4-乙酰基苯丙氨酸）时，人们担心它可能会从多肽中裂解出来，并掺入内源性蛋白质中。为了确定这种情况是否发生，我们进行了体外实验，评估细胞活力和氨基酸掺入内源性蛋白质的情况，实验中使用了[14C]4-乙酰基苯丙氨酸、4或[14C(U)]L-苯丙氨酸原代雄性大鼠肝细胞。[14C]4-乙酰基苯丙氨酸、4是通过2个放射化学步骤从[1-14C]乙酰氯制备的，总放射化学产率为8%，纯度为99.9%。结果表明，没有证据表明碳-14掺入肝细胞内源性蛋白质中，并且在0.1至1000μM的任何浓度下，[14C]pAcF与L-苯丙氨酸在细胞活力评估方面没有差异。
• Kupczyk-Subotkowska, Lidia; Saunders Jr., William H.; Shine, Henry J., Journal of the American Chemical Society, 1994, vol. 116, # 16, p. 7088 - 7093
  作者：Kupczyk-Subotkowska, Lidia、Saunders Jr., William H.、Shine, Henry J.、Subotkowski, Witold

  DOI：——

  日期：——