1-(2-aminoethyl-1,1-d2)-4-(4-nitrobenzoyl)piperidine | 228852-07-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2-aminoethyl-1,1-d2)-4-(4-nitrobenzoyl)piperidine
• 英文别名: [1-(2-Amino-1,1-dideuterioethyl)piperidin-4-yl]-(4-nitrophenyl)methanone
• CAS: 228852-07-1
• 化学式: C₁₄H₁₉N₃O₃
• 分子量: 279.307
• InChiKey: WPJPWWGJTFCROC-KBMKNGFXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  92.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-异硫氰基苯甲酸甲酯 、 1-(2-aminoethyl-1,1-d2)-4-(4-nitrobenzoyl)piperidine 以 四氢呋喃 为溶剂， 反应 1.0h， 以135 mg的产率得到3-(2-(4-(4-nitrobenzoyl)-piperidin-1-yl)-ethyl-2,2-d2)-1,2-dihydro-2-thioxoquinazoline
  参考文献：
  名称：

  Rapid synthesis of F-18 and H-2 dual-labeled altanserin, a metabolically resistant PET ligand for 5-HT2a receptors

  摘要：

  F-18 and H-2 dual-labeled altanserin (3, [F-18]d-ALT), a novel PET tracer for 5-HT2A receptors with metabolically resistant properties, was synthesized by [F-18]fluoride displacement of the corresponding deuterated nitro precursor in 32% yield (EOB) in 108 min with radiochemical purity 95% and specific activity >1000 mCi/mu mol (EOS). The key intermediate ethyl N-(2-chloroethyl-2,2-d(2))carbamate (7 was obtained by LiAlD4 reduction of a glycine ester (93%), chlorination and carbamoylation (79%). 4-(4-Nitrobenzoyl)piperidine (13) was synthesized (60%) by improving the published coupling reaction of p-nitrophenyltrimethylstannane (10), obtained from p-iodonitrobenzene and (CH3)(6)Sn-2 (94%), with 1-benzoylisonipecotic acid chloride (11) followed by acid hydrolysis. 13 was alkylated with 7 (82%), hydrolyzed and condensed with methyl o-isothiocyanatobenzoyate to provide with the precursor deuteronitmaltanserin (4, 75%).

  DOI：

  10.1002/(sici)1099-1344(199905)42:5<457::aid-jlcr206>3.0.co;2-0
• 作为产物：
  描述：

  1-benzoylpiperidine-4-carbonyl chloride 在 盐酸 、 bis(η3-allyl-μ-chloropalladium(II)) 、 2-己酮 、 potassium carbonate 、 potassium iodide 作用下， 生成 1-(2-aminoethyl-1,1-d2)-4-(4-nitrobenzoyl)piperidine
  参考文献：
  名称：

  Tan, P.-Z.; Baldwin, R. M.; Soufer, R., Journal of labelled compounds and radiopharmaceuticals, 1997, vol. 40, p. 130 - 132

  摘要：

  DOI：

文献信息

• Rapid synthesis of F-18 and H-2 dual-labeled altanserin, a metabolically resistant PET ligand for 5-HT2a receptors
  作者：Ping-Zhong Tan、Ronald M. Baldwin、Tao Fu、Dennis S. Charney、Robert B. Innis

  DOI：10.1002/(sici)1099-1344(199905)42:5<457::aid-jlcr206>3.0.co;2-0

  日期：1999.5

  F-18 and H-2 dual-labeled altanserin (3, [F-18]d-ALT), a novel PET tracer for 5-HT2A receptors with metabolically resistant properties, was synthesized by [F-18]fluoride displacement of the corresponding deuterated nitro precursor in 32% yield (EOB) in 108 min with radiochemical purity 95% and specific activity >1000 mCi/mu mol (EOS). The key intermediate ethyl N-(2-chloroethyl-2,2-d(2))carbamate (7 was obtained by LiAlD4 reduction of a glycine ester (93%), chlorination and carbamoylation (79%). 4-(4-Nitrobenzoyl)piperidine (13) was synthesized (60%) by improving the published coupling reaction of p-nitrophenyltrimethylstannane (10), obtained from p-iodonitrobenzene and (CH3)(6)Sn-2 (94%), with 1-benzoylisonipecotic acid chloride (11) followed by acid hydrolysis. 13 was alkylated with 7 (82%), hydrolyzed and condensed with methyl o-isothiocyanatobenzoyate to provide with the precursor deuteronitmaltanserin (4, 75%).
• Tan, P.-Z.; Baldwin, R. M.; Soufer, R., Journal of labelled compounds and radiopharmaceuticals, 1997, vol. 40, p. 130 - 132
  作者：Tan, P.-Z.、Baldwin, R. M.、Soufer, R.、Dyck, C. H. van、Charney, D. S.、Innis, R. B.

  DOI：——

  日期：——
• Tan; Soares; Staley, Journal of labelled compounds and radiopharmaceuticals, 1999, vol. 42, # SUPPL. 1, p. S66-S68
  作者：Tan、Soares、Staley、Seibyl、Baldwin、Van Dyck、Al-Tikriti、Fu、Charney、Innis

  DOI：——

  日期：——