1-azido-2-(phenylseleno)octane | 73501-69-6

• 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: 1-azido-2-(phenylseleno)octane
• 英文别名: [(1-Azidooctan-2-YL)selanyl]benzene；1-azidooctan-2-ylselanylbenzene
• CAS: 73501-69-6
• 化学式: C₁₄H₂₁N₃Se
• 分子量: 310.301
• InChiKey: VVBRJMHAWYCYAY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.09
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  14.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-azido-2-(phenylseleno)octane 在 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 乙醚 为溶剂， 生成 4-Methyl-N-(2-phenylselanyl-octyl)-benzenesulfonamide
  参考文献：
  名称：

  Pyrrolidines from olefins via radical cyclization

  摘要：

  2,4-Disubstituted N-tosylpyrrolidines were prepared from olefins via N-tosylaziridination, benseneselenolate ring-opening and reductive radical cyclization. Azidoselenation of olefins, followed by reduction, N-tosylation, N-allylation and reductive radical cyclization, afforded 3,4-disubstituted N-tosylpyrrolidines. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00217-2
• 作为产物：
  描述：

  2-溴辛基苯基硒化物 、 叠氮化钠 生成 1-azido-2-(phenylseleno)octane
  参考文献：
  名称：

  DENIS J. N.; VICENS J.; KRIEF A., TETRAHEDRON LETT., 1979, NO 29, 2697-2700

  摘要：

  DOI：

文献信息

• Substituted azides from selenium-promoted deselenenylation of azido selenides. Glycosylation reactions of protected 2-azido-2-deoxy-1-selenoglycopyranoses
  作者：Marco Tingoli、Marcello Tiecco、Lorenzo Testaferri、Andrea Temperini

  DOI：10.1039/c39940001883

  日期：——

  After activation with electrophilic selenenylating agents, the phenylseleno group of vicinal azido selenides can be easily substituted by nucleophiles to afford a variety of substituted azides.

  经过电亲核硒烷基化剂的活化，邻位叠氮硒化物的苯基硒基团可以很容易被亲核试剂替代，从而获得多种取代的叠氮化合物。
• 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.
• Pyrrolidines from olefins via radical cyclization
  作者：Vijay Gupta、Magnus Besev、Lars Engman

  DOI：10.1016/s0040-4039(98)00217-2

  日期：1998.4

  2,4-Disubstituted N-tosylpyrrolidines were prepared from olefins via N-tosylaziridination, benseneselenolate ring-opening and reductive radical cyclization. Azidoselenation of olefins, followed by reduction, N-tosylation, N-allylation and reductive radical cyclization, afforded 3,4-disubstituted N-tosylpyrrolidines. (C) 1998 Elsevier Science Ltd. All rights reserved.
• DENIS J. N.; VICENS J.; KRIEF A., TETRAHEDRON LETT., 1979, NO 29, 2697-2700
  作者：DENIS J. N.、 VICENS J.、 KRIEF A.

  DOI：——

  日期：——