cyclopenteno-1,2,3-selenadiazole | 35676-29-0

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: cyclopenteno-1,2,3-selenadiazole
• 英文别名: Cyclopenta-1,2,3-selenadiazol；5,6-dihydro-4H-cyclopenta[d]selenadiazole
• CAS: 35676-29-0
• 化学式: C₅H₆N₂Se
• 分子量: 173.076
• InChiKey: TVOIEPBZXPRAQH-UHFFFAOYSA-N

物化性质

• 沸点：
  239.6±43.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.02
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  cyclopenteno-1,2,3-selenadiazole 生成 trimethyleneselenoketene
  参考文献：
  名称：

  SANDER, W. W.;CHAPMAN, O. L., J. ORG. CHEM., 1985, 50, N 4, 543-544

  摘要：

  DOI：
• 作为产物：
  描述：

  环戊酮 在 selenium(IV) oxide 、 sodium acetate 作用下， 以 甲醇 为溶剂， 反应 5.33h， 生成 cyclopenteno-1,2,3-selenadiazole
  参考文献：
  名称：

  An efficient solventless synthesis of cycloalkeno-1,2,3-selenadiazoles, their antimicrobial studies, and comparison with parent semicarbazones

  摘要：

  A series of heterocyclic organoselenium compounds, cycloalkeno-1,2,3-selenadiazoles (cyclopenteno, cyclohexeno, cyclohepteno, and cycloocteno-1,2,3-selenadiazoles), was synthesized at room temperature in one step under solventless conditions from the corresponding semicarbazones. The synthesized 1,2,3-selenadiazoles and their parent semicarbazones were screened for their antimicrobial activity against various pathogenic bacteria using agar disc diffusion method. All compounds were found active against E. coli, S. aureus, S. typhi, and P. aeruginosa. Among all the tested selenadiazoles, cyclopenteno-1,2,3-selenadiazole showed excellent inhibition against highly resistant P. aeruginosa. It is observed that selenadiazoles showed higher activity compared with the respective semicarbazones.

  DOI：

  10.1007/s10593-015-1666-9

文献信息

• The reaction of 1,2,3-selenadiazole with olefins
  作者：Yutaka Nishiyama*、Yasunobu Hada、Kuniko Iwase、Noboru Sonoda*

  DOI：10.1016/s0022-328x(00)00484-8

  日期：2000.10

  treated with an excess amount of olefins at 130°C, the addition of a vinyl radical, which was generated in situ by the denitrogenation of 1,2,3-selenadiazoles, to a carbon–carbon double bond followed by intramolecular cyclization proceeded efficiently giving the corresponding dihydroselenophenenes in moderate to good yields along with the formation of the corresponding 1,4-diselenins and selenophenes

  当在130°C下用过量的烯烃处理由环状酮合成的1,2,3-硒代二唑时，会添加乙烯基，该乙烯基是通过1,2,3-硒代二唑进行脱氮而原位生成的。碳-碳双键随后分子内环化有效地进行，从而以中等至良好的收率得到了相应的二氢硒代苯烯，并形成了相应的副产物1，4-二硒代和硒代苯。在该反应中，在1,2,3-硒代二唑的合成中用作起始原料的酮的环上的碳原子数对产物的选择性起着重要作用。与由环状酮制得的1,2,3-硒代二唑的反应相反，在1,2的反应中，
• Microwave synthesis of bis(cycloalkeno)-1,4-diselenins: a novel source of Se for CdSe QDs
  作者：Aditi A. Jadhav、Priyesh V. More、Pawan K. Khanna

  DOI：10.1039/c7nj00793k

  日期：——

  cycloalkeno-1,2,3-selenadiazoles by a microwave irradiation (MW) method. The bi-radical dimerization reaction of 1,2,3-selenadiazoles was performed by a new synthetic strategy under solvent-free conditions using 100 Watt microwave irradiation for about 20 minutes. The current synthesis afforded a feasible approach for the preparation of various 1,4-diselenins. The so-prepared alkyl selenides were characterized

  本文介绍了通过微波辐射（MW）方法由相应的环烯基1,2,3-硒代二唑形成一系列的双（环烯基）-1,4-二硒精。1,2,3-硒代二唑的双自由基二聚反应是通过一种新的合成策略在无溶剂条件下使用100瓦特微波辐照约20分钟进行的。当前的合成为制备各种1，4-二硒精提供了可行的方法。如此制备的烷基硒化物通过各种光谱学工具表征。紫外线可见，FTIR，1 H，13 C，DEPT和77Se NMR光谱，ESI-MS和TGA分析。另外，双（环庚烯）-1,4-二硒精已被有效地用作合成CdSe量子点（QDs）的新型硒前体。这种富含硒的前体也可能用于制备其他金属硒化物。
• Tributylstannyl Radical-Catalyzed Reaction of 1,2,3-Selenadiazoles with Olefins or Dienes
  作者：Yutaka Nishiyama、Yasunobu Hada、Masahiro Anjiki、Kazuya Miyake、Sakiko Hanita、Noboru Sonoda

  DOI：10.1021/jo010893t

  日期：2002.3.1

  It was found that the reaction of 1,2,3-selenadiazoles derived from cyclic ketones with olefins or dienes was markedly promoted by a catalytic amount of tributylstannyl radical, which was generated in situ from tributylstannyl hydride or allyltributylstannane and AIBN, to give the corresponding dihydroselenophenes in moderate to good yields. In contrast, when 1,2,3-selenadiazoles prepared from linear

  已发现，催化量的三丁基锡烷基由三丁基锡烷基氢化物或烯丙基三丁基锡烷和AIBN催化生成，从而显着促进了环状酮衍生的1,2,3-硒代二唑与烯烃或二烯的反应。二氢硒代苯中度到良好的产量。相反，当使用由线性和芳族酮制得的1,2,3-硒代二唑作为底物时，没有发生相同的反应，炔烃形成了唯一的产物。
• Catalytic use of organostannyl radical: The reaction of 1,2,3-selenadiazole with olefins in the presence of a catalytic amount of tributyltin hydride
  作者：Yutaka Nishiyama、Yasunobu Hada、Masahiro Anjiki、Sakiko Hanita、Noboru Sonoda

  DOI：10.1016/s0040-4039(99)01286-1

  日期：1999.8

  When 1,2,3-selenadiazoles were treated with an excess amount of olefins in the presence of a catalytic amount of Bu3SnH and AIBN, the addition of a vinyl radical, which was generated in situ by the denitrogenation of 1,2,3-selenadiazoles, to the carbon-carbon double bond followed by intramolecular cyclization proceeded efficiently to afford the corresponding dihydroselenophenes in moderate to good

  当1,2,3- selenadiazoles是在卜催化量的存在下与烯烃的过量处理3 SNH和AIBN，增加了一个乙烯基基团，其中生成的原位由1,2-脱氮，将3-硒代二唑与碳-碳双键连接，然后进行分子内环化，可有效地制得相应的二氢硒代苯酚，收率中等至良好。
• Pannell, Keith H.; Mayr, Armin J.; Hoggard, Rodney, Chemische Berichte, 1983, vol. 116, # 1, p. 230 - 237
  作者：Pannell, Keith H.、Mayr, Armin J.、Hoggard, Rodney、McKennis, Jeffrey S.、Dawson, Jeffrey C.

  DOI：——

  日期：——

表征谱图