1,3-diselenole-2-selone | 53555-47-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 1,3-diselenole-2-selone
• 英文别名: 1,3-Diselenol-2-selon；vinylene triselenocarbonate；1,3-diselenol-2-selenone；1,3-Diselenol-2-selenon
• CAS: 53555-47-8
• 化学式: C₃H₂Se₃
• 分子量: 274.929
• InChiKey: HQQCZJHNGZWKAZ-UHFFFAOYSA-N

物化性质

• 熔点：
  115-116.5 °C(Solv: heptane (142-82-5))
• 沸点：
  307.1±25.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  6
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  1,3-diselenole-2-selone 在 三甲氧基磷 作用下， 以 苯 为溶剂， 反应 2.0h， 生成 delta-2,2'-联[1,3-二硒杂环戊烯]
  参考文献：
  名称：

  二硒化物与双（N，N-二烷基硒代氨基甲酰基）硒化物之间的新型交换反应。在四硒富勒烯（TSF）合成中的应用

  摘要：

  报道了高产率合成四硒富勒烯（TSF），涉及二硒化物与双（N，N-二烯丙基硒代氨基甲酰基）硒化物之间的新型酸催化的交换反应。

  DOI：

  10.1039/c39840000089
• 作为产物：
  描述：

  在 selenium 作用下， 以 甲醇 、 水 为溶剂， 反应 5.0h， 生成 1,3-diselenole-2-selone
  参考文献：
  名称：

  二硒化物与双（N，N-二烷基硒代氨基甲酰基）硒化物之间的新型交换反应。在四硒富勒烯（TSF）合成中的应用

  摘要：

  报道了高产率合成四硒富勒烯（TSF），涉及二硒化物与双（N，N-二烯丙基硒代氨基甲酰基）硒化物之间的新型酸催化的交换反应。

  DOI：

  10.1039/c39840000089

文献信息

• A Convenient Preparation of 1,3-Dithiole-2-thione and 1,3-Diselenole-2-selone Derivatives
  作者：K. Takimiya、A. Morikami、T. Otsubo

  DOI：10.1055/s-1997-787

  日期：1997.3

  A convenient one-pot preparation of 1,3-dithiole-2-thiones and 1,3-diselenole-2-selones substituted with phenyl, alkyl, alkylthio, hydroxymethyl, and formyl groups was accomplished from readily available acetylenes in good to excellent yields.

  方便的一锅法实现了对1,3-硫代二噁烷-2-硫酮和1,3-硒代二噁烷-2-硒酮的合成，这些化合物被苯基、烷基、烷基硫、羟甲基和甲酰基等取代基修饰，产率良好至优异，所用的原料是易得的乙炔。
• Thia-and/or selenafulvalenyl group-containing compound
  申请人：Idemitsu Kosan Co., Ltd.

  公开号：US05175280A1

  公开（公告）日：1992-12-29

  A thia- and/or selenafulvalenyl group-containing compound of the formula (I), ##STR1## wherein each of X.sub.1, X.sub.2, X.sub.3, X.sub.4, X'.sub.1, X'.sub.2, X'.sub.3 and X'.sub.4 is independently S or Se, Y is an electron donating or electron accepting group having a size which is not so large as to prevent molecular overlapping, m is an integer of 0 to 4, each of Z.sub.1, Z.sub.2, Z'.sub.1 and Z'.sub.2 is independently a hydrogen atom, C.sub.n H.sub.2n+1 in which n is an integer of 1 to 5, or alternatively, a combination of Z.sub.1 with Z.sub.2 and Z'.sub.1 with Z'.sub.2 is C.sub.n H.sub.2n in which n is an integer of 1 to 5, or X(C.sub.n H.sub.2n).sub.n', X in which X is S or Se and n' is an integer of 1 to 3, and each of R.sub.1, R.sub.2, R.sub.3, R'.sub.1, R'.sub.2 and R'.sub.3 is independently a hydrogen atom or C.sub.n H.sub.2n+1 in which n is an integer of 1 to 5. The compound has an electron donating nature and can be used to make electrically conductive complexes. The compound has an excellent thermal stability.

  具有以下结构的含有thia-和/或selenafulvalenyl基团的化合物（I）：其中X.sub.1、X.sub.2、X.sub.3、X.sub.4、X'.sub.1、X'.sub.2、X'.sub.3和X'.sub.4中的每一个独立地是S或Se，Y是一个具有不会妨碍分子重叠的大小的电子给予或电子接受基团，m是0到4的整数，Z.sub.1、Z.sub.2、Z'.sub.1和Z'.sub.2中的每一个独立地是氢原子，C.sub.n H.sub.2n+1，其中n是1到5的整数，或者，Z.sub.1与Z.sub.2和Z'.sub.1与Z'.sub.2的组合是C.sub.n H.sub.2n，其中n是1到5的整数，或X（C.sub.n H.sub.2n）.sub.n'，其中X是S或Se，n'是1到3的整数，R.sub.1、R.sub.2、R.sub.3、R'.sub.1、R'.sub.2和R'.sub.3中的每一个独立地是氢原子或C.sub.n H.sub.2n+1，其中n是1到5的整数。该化合物具有电子给予性质，可用于制备电导性复合物。该化合物具有出色的热稳定性。
• A General Method for the Synthesis of Alkylenedithio- and Bis(alkylenedithio)tetraselenafulvalenes
  作者：Kazuo Takimiya、Yoshiro Kataoka、Naoto Niihara、Yoshio Aso、Tetsuo Otsubo

  DOI：10.1021/jo034145a

  日期：2003.6.1

  A general synthetic method toward a series of alkylenedithio- and bis(alkylenedithio)tetraselenafulvalenes, i.e., methylenedithio- (MDT-TSF, 1a), ethylenedithio- (EDT-TSF, 1b), propylenedithio- (PDT-TSF, 1c), bis(methylenedithio)- (BMDT-TSF, 2a), bis(ethylenedithio)- (BETS, 2b), and bis(propylenedithio)tetraselenafulvalene (BPDT-TSF, 2c), as superior electron donors for organic conductors has been

  针对一系列亚烷基二硫基和双（亚烷基二硫基）四硒富勒烯的通用合成方法，即亚甲基二硫基（MDT-TSF，1a），乙二硫基（EDT-TSF，1b），丙烯二硫基（PDT-TSF，1c）作为有机导体的优良电子供体，已经开发出了（亚甲基二硫基）-（BMDT-TSF，2a），双（乙二硫基）-（BETS，2b）和双（丙烯二硫基）四硒富瓦烯（BPDT-TSF，2c）。该方法有利于从常用的合成中间体2-甲基硫基-3-（2-甲氧基羰基乙基硫基）-四硒富瓦烯（6）和2,6（7'）-双（甲基硫基）-3,7容易地获得一系列化合物。 （6′）-双（2-甲氧基羰基乙硫基）四硒富勒烯（7），分别用于不对称的亚烷基二硫代-和对称的双（亚烷基二硫代）-TSF。这些关键中间体很容易通过亚磷酸酯促进的4-甲硫基-5-（2-甲氧羰基乙硫基）-1,3-硒烯-2-硒酮（5）的偶联反应或通过TSF与LDA和3-硫代氰基丙酸甲酯的反应来制备
• Effective Synthesis of 1,3-Diselenole-2-selone-4,5-diselenolate (dsis) and its Utilization for the Synthesis of Selenocycle-fused Tetraselenafulvalene (TSF) Derivatives
  作者：Mie Kodani、Kazuo Takimiya、Yoshio Aso、Tetsuo Otsubo、Takashi Nakayashiki、Yoji Misaki

  DOI：10.1055/s-2001-16755

  日期：——

  A facile and effective synthetic procedure for 1,3-diselenole-2-selone-4,5-diselenolate (dsis, 2) has been established. The utilization of 2 for the synthesis of selenocycle-fused tetraselenafulvalene derivatives is also reported.

  已经建立了一种简便有效的 1,3-二硒醇-2-selone-4,5-二硒醇酯 (dsis, 2) 合成方法。还报道了利用2来合成硒环稠合的四硒富瓦烯衍生物。
• Neue selenreiche 1,3-Dichalkogenol-2-selone via 4,5-Dilithio-1,3-dichalkogenol-2-selone
  作者：Helmut Poleschner、Reiner Radeglia、Joachim Fuchs

  DOI：10.1016/0022-328x(92)83086-w

  日期：1992.4

  1,3-Dithiole-2-thione (1), 1,3-diselenole-2-selone (2), 1,3-thiaselenole-2-thione (3), 1,3-dithiole-2-selone (4), 1,3-diselenole-2-thione (5) and 1,3-thiaselenole-2-selone (6) are dilithiated with lithium diisopropyl amide in the 4/5 position, followed by selenation (thiolation) and complexation of the resulting heterocyclic diselenolates (dithiolates) to the zinc bis-chelates (tetrabutylammonium or tetraphenylphosphonium salts).These zinc complexes react with benzoyl chloride to the corresponding selenole and thiole esters. It is noteworthy that the heterocyclic thiones with one or two ring selenium atoms undergo ring transformation (Dimroth rearrangement) during the lithiation chalcogenation sequence, whilst the thione sulfur and one ring selenium atom change their places: 3 --> 1,3-dithiole-2-selone-4,5-diselenolate or dithiolate structure, 5 --> 1,3-thiaselenole-2-selone-4,5-diselenolate structure. This observed rearrangement is verified by independent synthetic pathways. The corresponding identical zinc chelates 12 and complex 18 result from the precursors 3 and 4, and 5 and 6, respectively. Trapping experiments support the conclusion that this rearrangement takes place already during lithiation. The zinc chelates and thiole and selenole esters are characterized in detail by IR and above all by C-13 and Se-77 NMR spectroscopy, including NMR shift values of the precursor heterocycles. The X-ray crystal structure determination of bis(tetraphenylphosphonium)-bis(1,3-thiaselenole-2-selone-4,5-diselenolato) zincate (18), obtained from 5, shows the rearrangement of 5 to the 1,3-thiaselenole-2-selone partial structure in 18.