1,4-dihydrobenzo[d][1,2]diselenine | 1160168-33-1

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 1,4-dihydrobenzo[d][1,2]diselenine
• 英文别名: 1,4-Dihydro-2,3-benzodiselenine；1,4-dihydro-2,3-benzodiselenine
• CAS: 1160168-33-1
• 化学式: C₈H₈Se₂
• 分子量: 262.072
• InChiKey: GYJHTWFGKQIEAM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.02
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1,4-dihydrobenzo[d][1,2]diselenine 以 邻二氯苯 为溶剂， 生成 1,3-二氢-2-苯并硒吩
  参考文献：
  名称：

  Quest for diatomic selenium

  摘要：

  Metallocene pentaselenides and elemental selenium were employed in an effort to generate diatomic selenium (Se2) under thermal conditions. Trapping experiments were carried out with six dienes. A successful formation of a diselenium adduct was observed in the case of 5,6-dimethylene-cyclohexa-1,3-diene (1a). The other dienes produced the corresponding dihydroselenophenes. The in-depth study of the limitations of our method to generate Se2 is described; a plausible mechanism rationalizing the observed results is proposed.

  DOI：

  10.1080/17415993.2010.513440
• 作为产物：
  描述：

  1,2-二(溴甲基)苯 在 selenium 、 一水合肼 、 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以72%的产率得到1,4-dihydrobenzo[d][1,2]diselenine
  参考文献：
  名称：

  通过硒还原选择性合成二硒化钠和二有机基二硒化氢的高效实用方法

  摘要：

  提出了一种在二有机基硒化物上选择性合成二有机基二硒化物的有效方法的研究。考虑到有机硒化合物报道之间的差异，我们希望建立一种可耐受的二有机二硒化物合成方法并研究其特性。我们优化了使用硒，NH 2 NH 2 ·H 2 O和NaOH制备二硒化钠的反应条件，并通过用各种烷基或芳基卤化物处理获得的二硒化钠，实现了适度到良好收率的选择性合成二有机二硒化钠（ 57–88％），重现性好。我们进一步研究了机械含义，溶剂变化的影响以及二有机基二硒化物的稳定性。

  DOI：

  10.1016/j.tet.2020.131720

文献信息

• Selenophilicity of Copper in Selenium-Carbon Bond Formation from Selenous Acid Using Cu(II)/Sn(II) Reagent
  作者：Joyanta Choudhury、Pradipta Sinha、S. Prabhakar、M. Vairamani、Sujit Roy

  DOI：10.1080/10426500802040349

  日期：2008.11.7

  A selenium transfer reaction from selenous acid to benzyl and alkyl halides is initiated in the presence of stannous chloride and a catalytic amount of cupric chloride resulting in the formation of the corresponding diorganoselenides and/or diorganodiselenides as the major products as indicated by 1 H, 13 C, 77 Se NMR, and MS. The reaction is characterized by a dual-metal effect at the selenium activation

  在氯化亚锡和催化量的氯化铜存在下引发从亚硒酸到苄基和烷基卤化物的硒转移反应，导致形成相应的二有机硒化物和/或二有机二硒化物作为主要产物，如 1 H、13 所示C、77 Se NMR 和 MS。该反应的特征在于硒活化和转移步骤中的双金属效应。因此，氯化亚锡、氯化铜和亚硒酸的初始反应产生α-Cu 2 Se。在氯化亚锡的额外帮助下，硒从后者转移到有机卤化物。
• Novel organo phosphorus–selenium heteroatom compounds from selenation of diamines
  作者：Guoxiong Hua、Rebecca A.M. Randall、Alexandra M.Z. Slawin、J. Derek Woollins

  DOI：10.1016/j.tet.2013.04.135

  日期：2013.7

  Reaction of Woollins' reagent (WR) with trans-1,2-cyclohexanediamine or 1,3-cyclohexanediamine, followed by treatment with o-xylylenedibromide in THF at room temperature surprisingly led to 3-phenyl-1,5-dihydrobenzo[e][1,3,2]diselenaphosphepine 3-selenide (3). However, using o-phenylenediamine, the same product together with 1,4-dihydrobenzo[d][1,2]diselenine (9) was obtained. Furthermore, treating WR with N,N'-dibenzylethane-1,2-diamine gave rise to 1,3-dibenzyl-2-phenyl-1,3,2-diazaphospholidine 2-selenide (10) and a zwitterionic product N-benzyl-N-(2-(benzylammonio)ethyl)-P-phenylphosphonamidodiselenoate (11). Unexpectedly, WR reacted with 2,2'-disulfanediyldianiline under identical conditions affording the known product: 2-phenyl-2,3-dihydrobenzo[d][1,3,2]thiazaphosphole 2-selenide (13). Three representative X-ray structures are reported. Crown Copyright (C) 2013 Published by Elsevier Ltd. All rights reserved.
• An efficient and practical method for the selective synthesis of sodium diselenide and diorganyl diselenides through selenium reduction
  作者：Yoo Jin Lim、Na Hye Shin、Chorong Kim、Ye Eun Kim、Hyunsung Cho、Myung-Sook Park、Sang Hyup Lee

  DOI：10.1016/j.tet.2020.131720

  日期：2020.12

  and practical method for the selective synthesis of diorganyl diselenides over diorganyl selenides are presented. Considering the discrepancies between reports on organoselenium compounds, we wanted to establish a tolerable synthetic method for diorganyl diselenides and investigate their characteristics. We optimized reaction conditions for sodium diselenide preparation using selenium, NH2NH2·H2O,

  提出了一种在二有机基硒化物上选择性合成二有机基二硒化物的有效方法的研究。考虑到有机硒化合物报道之间的差异，我们希望建立一种可耐受的二有机二硒化物合成方法并研究其特性。我们优化了使用硒，NH 2 NH 2 ·H 2 O和NaOH制备二硒化钠的反应条件，并通过用各种烷基或芳基卤化物处理获得的二硒化钠，实现了适度到良好收率的选择性合成二有机二硒化钠（ 57–88％），重现性好。我们进一步研究了机械含义，溶剂变化的影响以及二有机基二硒化物的稳定性。
• Quest for diatomic selenium
  作者：Andrzej Z. Rys、Erwin K.V. Schultz、David N. Harpp

  DOI：10.1080/17415993.2010.513440

  日期：2010.10.1

  Metallocene pentaselenides and elemental selenium were employed in an effort to generate diatomic selenium (Se2) under thermal conditions. Trapping experiments were carried out with six dienes. A successful formation of a diselenium adduct was observed in the case of 5,6-dimethylene-cyclohexa-1,3-diene (1a). The other dienes produced the corresponding dihydroselenophenes. The in-depth study of the limitations of our method to generate Se2 is described; a plausible mechanism rationalizing the observed results is proposed.