2-chloro-[1-14C]acetyl chloride | 74094-67-0

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机氯化物
• 英文名称: 2-chloro-[1-14C]acetyl chloride
• 英文别名: <1-14C>Chloroacetyl chloride；<1-14C>-Chloracetylchlorid；[¹⁴C]chloroacetyl chloride；chloro[1‐¹⁴C]acetyl chloride；chloro-[1-¹⁴C]acetyl chloride；[carbonyl-14C] chloroacetyl chloride；[(14)C]2-chloroacetyl chloride；Chloroacetyl chloride,[1-14c]；2-chloroacetyl chloride
• CAS: 74094-67-0
• 化学式: C₂H₂Cl₂O
• 分子量: 114.932
• InChiKey: VGCXGMAHQTYDJK-HQMMCQRPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  5
• 可旋转键数：
  1
• 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：

  2-chloro-[1-14C]acetyl chloride 、 N-(2-乙基-6-甲基苯基)甲亚胺 以92%的产率得到
  参考文献：
  名称：

  JABLONKAI, I.;MARTON, A. F.;DUTKA, F., RADIOCHEM. AND RADIOANAL. LETT., 1982, 53, N 4, 253-258

  摘要：

  DOI：
• 作为产物：
  描述：

  <1-14C>-Chloressigsaeure 在 氯化亚砜 作用下， 以 苯 为溶剂， 反应 2.0h， 生成 2-chloro-[1-14C]acetyl chloride
  参考文献：
  名称：

  Comparative metabolism and elimination of acetanilide compounds by rat

  摘要：

  1. C-14-labelled propachlor, alachlor, butachlor, metolachlor, methoxypropachlor and some of their mercapturic acid pathway metabolites (MAP) were given to rat either by gavage or by perfusion into a renal artery. MAP metabolites were isolated from bile and urine.2. Rat gavaged with propachlor and methoxypropachlor eliminated C-14 mostly in urine, whereas rat gavaged with alachlor, butachlor and metolachlor eliminated C-14 about equally divided between urine and faeces. When bile ducts were cannulated, the gavaged rat eliminated most of the C-14 in bile for all compounds. The amount of C-14 in bile from the propachlor-gavaged rat was less than that for the other acetanilides, with the difference being in the urine.3. The mercapturic acid metabolites 2-methylsulphinyl-N-(1-methylhydroxyethyl)-N-phenylacetamide and 2-methylsulphinyl-N-(1-methylmethoxyethyl)-N-phenylacetamide were isolated from the urine and bile of the methoxypropachlor-gavaged rat.4. Bile was the major route for C-14 elimination when MAP metabolites of alachlor, butachlor and metolachlor were perfused into a renal artery. Urine was the major route for C-14 elimination when MAP metabolites of propachlor and methoxypropachlor were perfused. Mercapturic acid conjugates were major metabolites in bile and urine when MAP metabolites were perfused.5. We conclude that alkyl groups on the phenyl portion of the acetanilide causes biliary elimination to be favoured over urinary elimination.

  DOI：

  10.3109/00498259409043297

文献信息

• Alkyne derivatives as tracers for metabotropic glutamate receptor binding
  申请人：Cosford Peter Nicholas David

  公开号：US20070060618A1

  公开（公告）日：2007-03-15

  The present invention is directed to isotopically labeled alkyne derivative compounds, particularly 11 C, 13 C, 14 C, 18 F, 15 O, 13 N, 35 S, 2 H, and 3 H labeled compounds. In particular, the present invention is directed to 11 C, 13 C, 14 C, 18 F, 15 O, 13 N, 35 S, 2 H, and 3 H labeled heterocyclic alkynes and methods of their preparation. The present invention further includes a method of use of the 11 C, 18 F, 15 O, or 13 N labeled heterocyclic alkyne compounds as tracers in positron emission tomography (PET) imaging, particularly in the study of metabolic conditions in mammals, specifically conditions modulated by metabotropic glutamate receptors subtype 5 (mGluR5).

  本发明涉及同位素标记的炔基衍生物化合物，特别是11C、13C、14C、18F、15O、13N、35S、2H和3H标记的化合物。具体而言，本发明涉及11C、13C、14C、18F、15O、13N、35S、2H和3H标记的杂环炔烃及其制备方法。本发明还包括将11C、18F、15O或13N标记的杂环炔烃化合物用作正电子发射断层扫描（PET）成像中的示踪剂的使用方法，特别是在哺乳动物代谢状况的研究中，特别是通过代谢型谷氨酸受体亚型5（mGluR5）调节的状况。
• Synthesis of [phenyl-U-14C]aryl and [8-14C]carboxy labeled tracers of vorinostat
  作者：Eric D. Soli、Matthew P. Braun

  DOI：10.1002/jlcr.1058

  日期：2006.4

  In support of a program to develop a treatment for advanced, refractory cutaneous T-cell lymphoma, two differentially [14C]-labeled forms of vorinostat, a histone deacetylase inhibitor, were synthesized for use in metabolism studies. Copyright © 2006 John Wiley & Sons, Ltd.

  为了支持开发治疗晚期难治性皮肤 T 细胞淋巴瘤的计划，合成了两种不同的 [14C] 标记形式的伏立诺他，一种组蛋白脱乙酰酶抑制剂，用于代谢研究。版权所有 © 2006 John Wiley & Sons, Ltd.
• Syntheses of dual-radioisotope-labeled CP-I, a GABAA receptor partial agonist
  作者：Yinsheng Zhang、Laura Greenfield、Yang Hong

  DOI：10.1002/jlcr.1889

  日期：2011.6.30

  of CP-I labeled at the right or left hand side with 14C or labeled with 3H at the right hand side were required. The two compounds labeled with 14C at the left or right hand side were synthesized in 2 and 5 radio-synthetic steps using [14C]2-chloroacetyl chloride and [14C]NaCN as starting radiolabeled materials, respectively. CP-I was labeled with tritium at the right hand side by a tritium de-halogenation

  CP-1 是一种有效的亚型选择性 GABAA 受体部分激动剂。由于在使用非放射性标记的 CP-I 的初步生物转化研究中观察到其在 C8 处的显着代谢裂解，需要在右侧或左侧用 14C 标记或在右侧用 3H 标记的 CP-I 的合成。在左侧或右侧用 14C 标记的两种化合物分别使用 [14C]2-氯乙酰氯和 [14C]NaCN 作为起始放射性标记材料在 2 步和 5 步放射性合成步骤中合成。通过氚脱卤法在右手边用氚标记CP-I。将多批放射性标记的 CP-I 混合以得到双放射性同位素标记的 CP-I。开发了一种有效的 [14C] 氟吡啶基咪唑方法，并且还实现了碘取代氟吡啶基咪唑的快速合成。讨论了这些合成的细节。版权所有 © 2011 John Wiley & Sons, Ltd.
• The synthesis of isotopologues of AZD7307: A selective β₂ -adrenoreceptor agonist
  作者：Lee P. Kingston、Michael J. Hickey、Charles S. Elmore

  DOI：10.1002/jlcr.3778

  日期：2019.9

  A medicinal chemistry program to develop potent and selective LABA compounds required the synthesis of both carbon-14 and stable-isotope labelled materials.  Carbon-14 labelled AZD7307 was successfully synthesised in 6 steps from [14C]chloroacetyl chloride in an overall radiochemical yield of 10%. In addition, the synthetic route of a stable labelled isotopomer of AZD7307 is also described and synthesised in four linear steps from [13C6]cyclohexylamine hydrochloride in an overall yield of 12%.

  开发有效且选择性 LABA 化合物的药物化学项目需要合成碳 14 和稳定同位素标记材料。  由[14C]氯乙酰氯经6步成功合成碳14标记的AZD7307，总放射化学产率为10%。此外，还描述了AZD7307的稳定标记同位素异构体的合成路线，并以[13C6]环己胺盐酸盐为原料，分四步线性合成，总产率为12%。
• Zerjatke, Pharmazie, 1985, vol. 40, # 12, p. 874 - 874
  作者：Zerjatke

  DOI：——

  日期：——