1-phenylseleno-2-azidocyclohexane | 116316-04-2

• 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-phenylseleno-2-azidocyclohexane
• 英文别名: [(1S,2S)-2-azidocyclohexyl]selanylbenzene
• CAS: 116316-04-2
• 化学式: C₁₂H₁₅N₃Se
• 分子量: 280.231
• InChiKey: MIFAAFGIKLRSSY-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.06
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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-phenylseleno-2-azidocyclohexane 在 吡啶 、 sodium periodate 作用下， 以 氯仿 为溶剂， 生成 2-叠氮环己烯
  参考文献：
  名称：

  苯叠氮化苯与烯烃的加成反应。将硒和氮新的立体定向引入有机分子。

  摘要：

  报道了通过添加烯烃直接引入PhSe和N 3官能团的第一个实例。在没有催化剂的情况下，将PhSeN 3加到简单的烯烃以及活化的烯烃中。该反应显然是立体定向的，而不是区域特异性的，显然是通过一个三元硒离子中间体进行的。

  DOI：

  10.1016/s0040-4039(00)95624-7
• 作为产物：
  描述：

  苯基硒基三氟甲烷磺酸酯 、 环己烯 在 sodium azide 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以72%的产率得到1-phenylseleno-2-azidocyclohexane
  参考文献：
  名称：

  Electrophilic Azido Selenenylation of Alkenes. A Simple Synthetic Route to Racemic Taxol Side Chain

  摘要：

  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.

  DOI：

  10.1080/00397919808007031

文献信息

• 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.
• 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.
• Phenylselenium azide addition to alkenes. A new and stereospecific introduction of Se and N into organic molecules.
  作者：Alfred Hassner、Ananda S. Amarasekara

  DOI：10.1016/s0040-4039(00)95624-7

  日期：——

  The first examples of direct introduction of PhSe and N3 functions by addition to olefins are reported. The addition of PhSeN3 to simple alkenes, as well as to activated alkenes takes place in the absence of a catalyst. The reaction proceeds stereospecifically but not regiospecifically, apparently via a 3-membered selenonium ion intermediate.

  报道了通过添加烯烃直接引入PhSe和N 3官能团的第一个实例。在没有催化剂的情况下，将PhSeN 3加到简单的烯烃以及活化的烯烃中。该反应显然是立体定向的，而不是区域特异性的，显然是通过一个三元硒离子中间体进行的。