5-Azido-4-phenylselanyl-pentanoic acid methyl ester | 136061-61-5

• 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-4-phenylselanyl-pentanoic acid methyl ester
• 英文别名: Methyl 5-azido-4-phenylselanylpentanoate；methyl 5-azido-4-phenylselanylpentanoate
• CAS: 136061-61-5
• 化学式: C₁₂H₁₅N₃O₂Se
• 分子量: 312.23
• InChiKey: ULJNFHCCDNYVOC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.07
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  40.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-Azido-4-phenylselanyl-pentanoic acid methyl ester 在 silica gel 、 三苯基膦 作用下， 生成 5-(Phenylseleno)-2-piperidone
  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：

  4-戊烯酸甲酯 、 二苯基二硒醚 在 sodium azide 、 碘苯二乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以83%的产率得到5-Azido-4-phenylselanyl-pentanoic acid methyl ester
  参考文献：
  名称：

  Novel azido-phenylselenenylation of double bonds. Evidence for a free-radical process

  摘要：

  A simple and mild azido-phenylselenenylation of terminal alkenes, which proceeds with complete anti-Markovnikov regioselectivity, has been developed. This reaction occurs when the alkenes are treated with (diacetoxyiodo)benzene, sodium azide, and diphenyl diselenide in dichloromethane at room temperature. The observed regioselectivity can be explained by assuming that the addition process is initiated by azido radicals. This was further supported by the results obtained starting from 1,6-heptadiene and from beta-pinene. Under the same conditions, efficient azido-phenylselenenylation of symmetrical olefins, 3,4-dihydro-2H-pyran, methyl acrylate, and vinyl crotonate can also be effected.

  DOI：

  10.1021/jo00024a020

文献信息

• Electrophilic Azido Selenenylation of Alkenes. A Simple Synthetic Route to Racemic Taxol Side Chain
  作者：Marcello Tiecco、Lorenzo Testaferri、Andrea Temperini、Luana Bagnoli、Francesca Marini、Claudio Santi

  DOI：10.1080/00397919808007031

  日期：1998.6

  Simple alkenes react with PhSeOTf and NaN3 in MeCN to afford beta-phenylseleno azides as the result of a stereospecific trans addition. The regioselectivity of the process is determined by the structure of the alkene.
• Novel azido-phenylselenenylation of double bonds. Evidence for a free-radical process
  作者：Marco Tingoli、Marcello Tiecco、Donatella Chianelli、Roberta Balducci、Andrea Temperini

  DOI：10.1021/jo00024a020

  日期：1991.11

  A simple and mild azido-phenylselenenylation of terminal alkenes, which proceeds with complete anti-Markovnikov regioselectivity, has been developed. This reaction occurs when the alkenes are treated with (diacetoxyiodo)benzene, sodium azide, and diphenyl diselenide in dichloromethane at room temperature. The observed regioselectivity can be explained by assuming that the addition process is initiated by azido radicals. This was further supported by the results obtained starting from 1,6-heptadiene and from beta-pinene. Under the same conditions, efficient azido-phenylselenenylation of symmetrical olefins, 3,4-dihydro-2H-pyran, methyl acrylate, and vinyl crotonate can also be effected.
• Synthesis of nitrogen-containing heterocycles from the azido-selenenylation products of unsaturated carbonyl compounds
  作者：Marco Tingoli、Marcello Tiecco、Lorenzo Testaferri、Roberto Andrenacci、Roberta Balducci

  DOI：10.1021/jo00074a042

  日期：1993.10

  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.