[羧基-14C]苯甲醛 | 14734-27-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: [羧基-14C]苯甲醛
• 英文名称: [carbonyl‐¹⁴C] benzaldehyde
• 英文别名: [carboxyl-¹⁴C]benzaldehyde；benzaldehyde-[carbonyl-14C]；benzaldehyde-α-14C；[7-14C]benzaldehyde；[14C]benzaldehyde；[α-¹⁴C]benzaldehyde；benzaldehyde
• CAS: 14734-27-1
• 化学式: C₇H₆O
• 分子量: 108.113
• InChiKey: HUMNYLRZRPPJDN-ZQBYOMGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  8
• 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：

  [羧基-14C]苯甲醛 在 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 以47%的产率得到
  参考文献：
  名称：

  A convenient synthesis of [14C]-labeled aromatic iodides as versatile synthetic intermediates

  摘要：

  DOI：

  10.1002/jlcr.1295
• 作为产物：
  描述：

  benzo[cyano-¹⁴C]nitrile 在 镍 甲酸 作用下， 以 水 为溶剂， 反应 1.0h， 生成 [羧基-14C]苯甲醛
  参考文献：
  名称：

  Synthesis of carbon-14 labelled l,5 diaryl-[5-14C]-l,2,3-triazolines

  摘要：

  两种 1,2,3-三唑啉抗惊厥药 1-(4-甲基磺酰基苯基)-5-(4-甲氧基苯基)-1,2,3-三唑啉和 l-(4-甲基磺酰基苯基)-5-苯基-1,2,3-三唑啉都在 5 位上用碳-14 标记，它们是通过 5 个步骤合成的。Copyright © 2003 John Wiley & Sons, Ltd. All Rights Reserved.

  DOI：

  10.1002/jlcr.794

文献信息

• Use of Dibutyl[14C]formamide as a Formylating Reagent in theVilsmeier-Haack Reaction and Synthesis of a14C-Labeled Novel Phosphodiesterase-4 (PDE-4) Inhibitor
  作者：Jonathan Z. Ho、Charles S. Elmore、Michael A. Wallace、Dan Yao、Matthew P. Braun、Dennis C. Dean、David G. Melillo、Cheng-yi Chen

  DOI：10.1002/hlca.200590075

  日期：2005.5

  high-yielding synthesis of dibutyl[14C]formamide ([14C]DBF; 1) from 14CO2 was developed (Scheme 1): reaction of LiBEt3H and 14CO2 followed by aqueous workup gave H14CO2H in high yield. Conversion of the [14C]formic acid to 1 was effected by a standard carbodiimide coupling procedure. The utility of 1 as an alternative to dimethyl[14C]formamide ([14C]DMF) in alkylation reactions and in the [14C]Vilsmeier–Haack

  开发了一种由14 CO 2简单，高产的二丁基[ 14 C]甲酰胺（[ 14 C] DBF; 1）的合成方案（方案1）：LiBEt 3 H和14 CO 2反应，然后进行水后处理，得到H 14 CO 2的H高产率。通过标准的碳二亚胺偶联方法将[ 14 C]甲酸转化为1。的效用1作为替代二甲基[ 14 C]甲酰胺（[ 14 C] DMF）在烷基化反应和在[ 14C]证明了几种底物的Vilsmeier-Haack反应（表2）。甲14 C标记的磷酸二酯酶-4（PDE-4）抑制剂，[ 14 C] - 2，通过应用这种技术的（合成流程2）。
• Synthesis of paclitaxel-C3′-14C
  作者：Donald G. Walker、Robert T. Standridge、John E. Swigor

  DOI：10.1002/jlcr.2580360512

  日期：1995.5

  Reductive cleavage of the C13 side chain of paclitaxel (3) followed by regioselective silylation gave 7-triethylsilylbaccatin III (6). Successive reaction of L-threonine methyl ester hydrochloride (7) with tertbutoxydiphenylchlorosilane, benzaldehyde-C7-14C and acetoxyacetyl chloride/ triethylamine gave a 92:8 ratio (NMR) of azetidinones 10:11 in 57% yield from 7. Removal of the chiral auxiliary led to 16, which after 3-O-triethylsilylation and N-benzoylation provided (3R,4S)-cis-1-benzoyl-3-O-(triethylsilyl)-4-phenylazetidin-2-one-C4-14C (18). Coupling of 18 and 6 followed by deprotection gave 1.12 g of paclitaxel-C3′-14C (2) having a specific activity of 16.4 mCi/mmol and a radiochemical purity of 96%.

  对紫杉醇（3）的 C13 侧链进行还原裂解，然后进行区域选择性硅烷化反应，得到了 7-三乙基硅基巴卡丁 III（6）。将 L-苏氨酸甲酯盐酸盐（7）与叔丁氧基二苯基氯硅烷、苯甲醛-C7-14C 和乙酰氧乙酰氯/三乙胺连续反应，从 7 中得到 92:8（核磁共振）比的氮杂环丁酮 10:11，收率为 57%。去除手性助剂后得到 16，经过 3-O-三乙基硅烷化和 N-苯甲酰化后得到 (3R,4S)-顺式-1-苯甲酰基-3-O-（三乙基硅烷）-4-苯基氮杂环丁烷-2-酮-C4-14C（18）。将 18 和 6 偶联，然后去保护，得到 1.12 克紫杉醇-C3′-14C (2)，其比活度为 16.4 mCi/mmol，放射化学纯度为 96%。
• Preparation of four 1,4-dihydropyridine derivatives (DHPs) labeled with carbon-14
  作者：Mohammad Amin Ahmadi Faghih、Mohammad Hossein Moslemin、Gholamhossein Shirvani、Mohsen Javaheri

  DOI：10.1002/jlcr.3642

  日期：2018.8

  of DHPs compounds and the need for examining the mechanism of their effect, mandated us to synthesize a number of carbon-14 labeled 1,4-dihydropyridine derivatives for pharmacological studies. Simple preparation and suitable radiochemical yield were advantages of this preparation.

  DHPs 化合物的重要性和研究其作用机制的必要性，要求我们合成许多碳 14 标记的 1,4-二氢吡啶衍生物用于药理学研究。该制剂的优点是制备简单，放射化学收率合适。
• Bohlmann,F. et al., Chemische Berichte, 1964, vol. 97, p. 809 - 814
  作者：Bohlmann,F. et al.

  DOI：——

  日期：——
• Synthesis of 6-chloro 2(-ethylamino)-4-methyl-4-phenyl-[-4-14C]-4H-3,1-benzoxazine (Etifoxine)
  作者：Elmostafa Azim、Jean Michel Dupuy、Françis Lepage、Annie Veyre、Jean Claude Madelmont

  DOI：10.1002/(sici)1099-1344(199711)39:11<907::aid-jlcr38>3.0.co;2-2

  日期：1997.11

  Carbonation of phenyl lithium with (CO2)-C-14, followed by reduction of [(CO2)-C-14] benzoic acid, led to [alpha-C-14] benzyl alcohol 3, the oxidation of which afforded the [alpha-C-14] benzaldehyde 4. The latter, then condensed with pivoylamide 6 (trimethyl acetamide-N-(2-lithio-4chlorophenyl) gave 5-chloro-2 (t-Butylamide)-alpha-phenyl-[-alpha-C-14] benzyl alcohol 2 which was then oxidized to ketone 8 which it self were subsequently hydrolysed to 5-chloro-2-amino-[-alpha-C-14]benzophenone 9. Grignard reaction of 9 with methylmagnesium iodide gave 5-chloro-2-amino-alpha-methyl-alpha-phenyl-[-alpha-C-14] benzyl alcohol 10. Treatment of the alcohol 10 with ethylthioisocyanate, followed by cyclisation led to 6-chloro-2-(ethylamino)-4-methyl-4-phenyl-[-4-C-14]-benzoxazine 12. The latter was acidified to give rise to Etifoxine hydrochloride 13 in an overall yield of about 31%based on [C-14] barium carbonate.