<7-(14)C>-benzoyl chloride | 10425-64-6

• 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: <7-(14)C>-benzoyl chloride
• 英文别名: benzoyl chloride-C7-¹⁴C；[carboxyl-14C]-benzoyl chloride；[1-14C]-benzoyl chloride；[1-14C]benzoyl chloride；benzoic-7-14C chloride；[14C]benzoyl chloride；benzoyl chloride
• CAS: 10425-64-6
• 化学式: C₇H₅ClO
• 分子量: 142.558
• InChiKey: PASDCCFISLVPSO-WGGUOBTBSA-N

物化性质

• 沸点：
  70-73 °C(Press: 10 Torr)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  <7-(14)C>-benzoyl chloride 在 2-喹啉硫醇 氢气 作用下， 以 甲苯 为溶剂， 生成 [羧基-14C]苯甲醛
  参考文献：
  名称：

  Hege; Weymann; Lietz, Arzneimittel-Forschung/Drug Research, 1984, vol. 34, # 8, p. 843 - 849

  摘要：

  DOI：
• 作为产物：
  描述：

  苯甲酸-羧基-14C 在 氯化亚砜 作用下， 反应 1.0h， 以82%的产率得到<7-(14)C>-benzoyl chloride
  参考文献：
  名称：

  [羰基-14C]-4-苯甲酰基苯甲酸的合成，一种光标记试剂

  摘要：

  [羰基-14C]-4-苯甲酰基苯甲酸是一种光标记试剂，是由 [羧基-14C]-苯甲酸以 57% 的放射性产率合成的，具有高比活性。放射性合成可以阐明以前使用苯甲酸甲酯进行未标记合成的机制。实验条件的改进导致放射性苯甲酰苯甲酸衍生物的新合成具有良好的产率。版权所有 © 1999 John Wiley & Sons, Ltd.

  DOI：

  10.1002/(sici)1099-1344(199912)42:12<1175::aid-jlcr272>3.0.co;2-5

文献信息

• Heterocyclization Reaction ofα-Imino Carbonyl Compounds− Derivatives of 2,5-Dihydro-1H-imidazole Nitroxides
  作者：Galina A. Roshchupkina、Natalie V. Pervukhina、Tatjana V. Rybalova、Yuri V. Gatilov、Alexey B. Burdukov、Vladimir A. Reznikov

  DOI：10.1002/ejoc.200300212

  日期：2003.11

  α-Imino carbonyl compounds − derivatives of 3-imidazoline nitroxides − were found to undergo heterocyclization reactions, yielding oxazole and 1,3,5-triazine derivatives. The most probable course of the reaction was suggested by the radioactive label method. The structures of the heterocycles synthesized were verified by X-ray analysis of the mixed-ligand complexes with copper hexafluoroacetylacetonate

  α-亚氨基羰基化合物 - 3-咪唑啉氮氧化物的衍生物 - 被发现发生杂环化反应，产生恶唑和 1,3,5-三嗪衍生物。放射性标记法表明了最可能的反应过程。合成的杂环的结构通过与六氟乙酰丙酮酸铜的混合配体配合物的 X 射线分析来验证。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)
• Distinction between polar and electron-transfer routes. A mechanistic study on the Wittig reactions of nonstabilized ylides
  作者：Hiroshi Yamataka、Katsushi Nagareda、Tsutomu Takatsuka、Katsuhiro Ando、Terukiyo Hanafusa、Shigeru Nagase

  DOI：10.1021/ja00072a008

  日期：1993.9

  The Wittig reaction of nonstabilized ylides with benzaldehyde and benzophenone was investigated in detail by means of carbonyl- 14 C kinetic isotope effects, substituent effects, and isotope-scrambling and probe experiments. The reaction with benzophenone gave the carbon isotope effects and the Hammett p values of considerable magnitude both in Li salt-free and salt-present conditions. In contrast

  通过羰基- 14 C 动力学同位素效应、取代基效应以及同位素加扰和探针实验，详细研究了不稳定叶立德与苯甲醛和二苯甲酮的 Wittig 反应。与二苯甲酮的反应在无锂和含盐条件下都产生了相当大的碳同位素效应和哈米特 p 值。相比之下，它们与苯甲醛的反应非常小。烯酮异构化和脱卤探针实验表明不稳定的叶立德有足够的能力将电子转移给苯甲醛和二苯甲酮
• Synthesis of the NK3 receptor antagonist AZD2624 in C-14-, H-3- and C-13-labeled forms
  作者：Charles S. Elmore、Peter N. Dorff、Mark E. Powell、James E. Hall、Thomas R. Simpson

  DOI：10.1002/jlcr.1858

  日期：2011.5.15

  treatment for schizophrenia, three labeled forms of the NK3 receptor antagonist AZD2624 have been prepared. [3H2]AZD2624 was synthesized by tritiodehalogenation for use in receptor occupancy and autoradiographic studies. [13C6]AZD2624 was prepared for use as an internal standard through the intermediacy of [13C6]isatin, and two C-14 isotopomers of AZD2624 were prepared from [14C]benzoic acid and [14C]isatin

  为了支持开发精神分裂症抗精神病药物治疗的计划，已经制备了三种标记形式的 NK3 受体拮抗剂 AZD2624。[3H2]AZD2624 是通过三碘脱卤合成的，用于受体占用和放射自显影研究。[13C6]AZD2624 通过 [13C6] 靛红作为内标制备，AZD2624 的两种 C-14 同位素由 [14C] 苯甲酸和 [14C] 靛红制备，用于各种 DMPK 研究。版权所有 © 2011 John Wiley & Sons, Ltd.
• The reaction of penta-O-benzoyl-d-glucopyranose with piperidine: characterization of the products isolated and study of the reaction mechanism
  作者：Amelia E Salinas

  DOI：10.1016/s0008-6215(99)00029-4

  日期：1999.3

  same reaction, it was found that N-benzoylpiperidine is formed at the expense of benzoyloxy-C-1, piperidinium benzoate arises mainly from benzoyloxy-C-2, and the benzoyloxy groups originally attached to C-3, C-4, and C-6 remain in the major product of the reaction. These results demonstrate that the first compound produced in the reaction is N-(3,4,6-tri-O-benzoyl-β- d -glucopyranosyl)piperidine, which

  摘要五-O-苯甲酰基-d-吡喃葡萄糖与哌啶的反应生成N-（2,3,6-三-O-苯甲酰基-β-d-吡喃葡萄糖基）哌啶（44.1％），N-（2,4， 6-三-O-苯甲酰基-β-d-吡喃葡萄糖基）哌啶（1.5％），N-苯甲酰基哌啶和苯甲酸哌啶鎓（每摩尔底物约两种摩尔的两种产物）。当几个含有选择性地被14 C标记的苯甲酰氧基的五-O-苯甲酰基-d-吡喃葡萄糖进行同一反应时，发现以苯甲酰氧基-C-1为代价形成了N-苯甲酰基哌啶，苯甲酸哌啶主要来自苯甲酰氧基。 -C-2和最初连接到C-3，C-4和C-6的苯甲酰氧基保留在反应的主要产物中。这些结果表明，反应中产生的第一个化合物是N-（3,4,6-三-O-苯甲酰基-β-d-吡喃葡萄糖基）哌啶，无法分离，因为它经历了两个连续的苯甲酰迁移：从O-3迁移到O-2得到2,4,6-tri-O-苯甲酸酯，然后从O-4迁移到O-3得到2,3,6-三-O-苯甲酸酯。提出
• Synthesis of [¹⁴C] - and [¹³C₆]-labeled tipranavir and its potential hydroxyl metabolite and the glucuronide conjugate
  作者：Bachir Latli、Matt Hrapchak、John A. Easter、Wayne T. Stolle、Karl Grozinger、Dhileepkumar Krishnamurthy、Chris H. Senanayake

  DOI：10.1002/jlcr.1528

  日期：2008.7

  Tipranavir or Aptivus® is a non-peptidic protease inhibitor approved for the combination treatment with ritonavir of HIV infection. Tipranavir labeled with radioactive and stable isotopes of carbon was required for drug metabolism (excretion, distribution, and absorption) studies and to develop bioanalytical methods needed for the support of clinical studies. [7-14C]-Benzoic acid and uniformly labeled benzoic acid (ring-13C6 99 at% 13C) were used to prepare [14C]- and [13C6]-labeled tipranavir, respectively. Radioactively labeled tipranavir was prepared with a specific activity of 54 mCi/mmol (2GBq/mmol); it was necessary to dilute its specific activity with unlabeled tipranavir to 28 mCi/mmol (46.45 µCi/mg) because of its instability. The N-hydroxyl metabolite (12) and the glucuronide conjugate (13), the most abundant metabolites of tipranavir (when administered in conjunction with ritonavir) were also synthesized. Copyright © 2008 John Wiley & Sons, Ltd.

  替普瑞那韦或 Aptivus® 是一种非肽蛋白酶抑制剂，已被批准与利托那韦联合治疗艾滋病病毒感染。在进行药物代谢（排泄、分布和吸收）研究和开发支持临床研究所需的生物分析方法时，需要使用放射性和稳定碳同位素标记的替普瑞那韦。[7-14C]-苯甲酸和均匀标记的苯甲酸（环-13C6 99 at% 13C）分别用于制备[14C]-和[13C6]-标记的替拉那韦。放射性标记的替拉那韦的比活度为 54 mCi/mmol（2GBq/mmol）；由于其不稳定性，必须用未标记的替拉那韦将其比活度稀释至 28 mCi/mmol（46.45 µCi/mg）。此外，还合成了替拉那韦最丰富的代谢物 N- 羟基代谢物 (12) 和葡萄糖醛酸结合物 (13)（与利托那韦同时服用时）。Copyright © 2008 John Wiley & Sons, Ltd. All Rights Reserved.