5-Azido-2-[6-(5-azido-2-methoxycarbonyl-4-phenylselanyl-pentanoyl)-pyridine-2-carbonyl]-4-phenylselanyl-pentanoic acid methyl ester | 151476-75-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 5-Azido-2-[6-(5-azido-2-methoxycarbonyl-4-phenylselanyl-pentanoyl)-pyridine-2-carbonyl]-4-phenylselanyl-pentanoic acid methyl ester
• CAS: 151476-75-4
• 化学式: C₃₁H₃₁N₇O₆Se₂
• 分子量: 755.55
• InChiKey: ROGGYHONVMHDIP-UHFFFAOYSA-N

反应信息

• 作为反应物：
  描述：

  5-Azido-2-[6-(5-azido-2-methoxycarbonyl-4-phenylselanyl-pentanoyl)-pyridine-2-carbonyl]-4-phenylselanyl-pentanoic acid methyl ester 在 三苯基膦 作用下， 以 苯 为溶剂， 反应 0.5h， 以78%的产率得到5,5''-Bis-phenylselanyl-1,4,5,6,1'',4'',5'',6''-octahydro-[2,2';6',2'']terpyridine-3,3''-dicarboxylic acid dimethyl ester
  参考文献：
  名称：

  Synthesis of nitrogen-containing heterocycles from the azido-selenenylation products of unsaturated carbonyl compounds

  摘要：

  Terminal alkenes containing a remote carbonyl group reacted with iodobenzene diacetate, diphenyl diselenide, and sodium azide to afford the products of azido-phenylselenenylation of the double bond. Owing to its radical nature, this reaction proceeded with complete anti-Markovnikov regioselectivity. Under the influence of triphenylphosphine in benzene the azido group reacted with the carbonyl function to afford the corresponding ring-closure reaction products containing a carbon nitrogen double bond. Thus, starting from beta,gamma- or gamma,delta-unsaturated esters, the corresponding cyclic imino ethers were obtained. These could not be isolated but were directly transformed into beta-(phenylseleno) gamma-lactams or gamma-(phenylseleno) delta-lactams. The phenylseleno derivatives of tetrahydropyridine were formed starting both from gamma,delta-unsaturated ketones and from alpha-allyl beta-keto esters. In the latter case, the cyclization reaction is chemoselective and involves the ketonic carbonyl. The oxidation of these compounds with hydrogen peroxide directly produced the corresponding pyridines via selenoxide elimination followed by dehydrogenation. This simple reaction sequence represents a very useful general method to build up a 2-substituted pyridine ring. Several alkyl-, aryl-, and heteroarylpyridines, bipyridines, and a terpyridine have been prepared.

  DOI：

  10.1021/jo00074a042
• 作为产物：
  描述：

  二苯基二硒醚 、 2-[6-(2-Methoxycarbonyl-pent-4-enoyl)-pyridine-2-carbonyl]-pent-4-enoic acid methyl ester 在 sodium azide 、 碘苯二乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以60%的产率得到5-Azido-2-[6-(5-azido-2-methoxycarbonyl-4-phenylselanyl-pentanoyl)-pyridine-2-carbonyl]-4-phenylselanyl-pentanoic acid methyl ester
  参考文献：
  名称：

  Synthesis of nitrogen-containing heterocycles from the azido-selenenylation products of unsaturated carbonyl compounds

  摘要：

  Terminal alkenes containing a remote carbonyl group reacted with iodobenzene diacetate, diphenyl diselenide, and sodium azide to afford the products of azido-phenylselenenylation of the double bond. Owing to its radical nature, this reaction proceeded with complete anti-Markovnikov regioselectivity. Under the influence of triphenylphosphine in benzene the azido group reacted with the carbonyl function to afford the corresponding ring-closure reaction products containing a carbon nitrogen double bond. Thus, starting from beta,gamma- or gamma,delta-unsaturated esters, the corresponding cyclic imino ethers were obtained. These could not be isolated but were directly transformed into beta-(phenylseleno) gamma-lactams or gamma-(phenylseleno) delta-lactams. The phenylseleno derivatives of tetrahydropyridine were formed starting both from gamma,delta-unsaturated ketones and from alpha-allyl beta-keto esters. In the latter case, the cyclization reaction is chemoselective and involves the ketonic carbonyl. The oxidation of these compounds with hydrogen peroxide directly produced the corresponding pyridines via selenoxide elimination followed by dehydrogenation. This simple reaction sequence represents a very useful general method to build up a 2-substituted pyridine ring. Several alkyl-, aryl-, and heteroarylpyridines, bipyridines, and a terpyridine have been prepared.

  DOI：

  10.1021/jo00074a042