2,3-dihydro-2-phenyl-1,3-dithiolo<4,5-e><1,4>dithiin-6-one | 111082-46-3

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2,3-dihydro-2-phenyl-1,3-dithiolo<4,5-e><1,4>dithiin-6-one
• 英文别名: 2,3-dihydro-2-phenyl-1,3-dithio<4,5-e><1,4>-dithiin-6-one；2,3-dihydro-2-phenyl-1,3-dithiolo-[4,5-e] [1,4]dithiin-6-one；4,5-phenylethylenedithio-1,3-dithiole-2-one；5-phenylethylenedithio-1,3-dithiole-2-one；5-Phenyl-5,6-dihydro-[1,3]dithiolo[4,5-b][1,4]dithiin-2-one
• CAS: 111082-46-3
• 化学式: C₁₁H₈OS₄
• 分子量: 284.448
• InChiKey: GHJGZBMNAFFSRM-UHFFFAOYSA-N

物化性质

• 沸点：
  454.3±55.0 °C(Predicted)
• 密度：
  1.56±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  118
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,3-dihydro-2-phenyl-1,3-dithiolo<4,5-e><1,4>dithiin-6-one 在 air 、 KOH 作用下， 以 甲醇 、 乙腈 为溶剂， 生成 (tetraphenylphosphonium)(Ni(phdt)2)
  参考文献：
  名称：

  Electrochemistry and strong near-IR absorption of the [Ni(dphdt)2]n complexes (n=−1, 0; dphdt=5,6-diphenyl-1,4-dithiin-2,3-dithiolate); X-ray crystal structure of (Ph4P)[Ni(dphdt)2](CH2Cl2)

  摘要：

  Nickel bisdithiolene complexes C-x[Ni(dphdt)(2)] (x = 1 or 0.1, C = tetrabutylammonium (n-Bu4N+); x = 1, C = tetraphenylphosphonium (Ph4P+); dphdt=5,6-diphenyl-1,4-dithiin-2,3-dithiolate) have been synthesized and characterized. The molecular structure of (ph(4)P) [Ni(dphdt)(2)] (CH2CI2) was determined by X-ray analysis. Ni(S2C2S2)(2) core is planar and stacking along the c-axis and the shortest intra-stack S ... S distance is 4.529 Angstrom. According to the cyclic voltammetry of (n-Bu4N) [Ni(dphdt)(2)], two phenyl groups on the dphdt ligand decrease the electron density on the Ni(S2C2S2)(2) core and increase the oxidation potentials compared to those of the (n-Bu4N) [Ni(dddt)(2)] complex (dddt = 5,6-dihydro-1,4-dithiin-2,3-dithiolate). Near-IR spectra of the complexes show that phenyl substitution on the ligand does not give rise to the evident change in transition energy due to the lack of coplanarity with the Ni(S2C2S2)(2) core. (C) 2000 Elsevier Science Ltd All rights reserved.

  DOI：

  10.1016/s0277-5387(99)00379-4
• 作为产物：
  描述：

  4,5-(phenyl-ethylenedithio)-1,3-dithiole-2-thione 在 mercury(II) diacetate 作用下， 以 氯仿 为溶剂， 以51%的产率得到2,3-dihydro-2-phenyl-1,3-dithiolo<4,5-e><1,4>dithiin-6-one
  参考文献：
  名称：

  苯基取代的2,3-二氢-1,3-二硫代[4,5-e] [1,4]二硫代-6-硫酮的新合成

  摘要：

  的简便合成4和（±） - 6进行经由狄尔斯-阿尔德型[2 + 4]的低聚二烯的环加成反应8与苯乙烯或吨通过热反应分别芪，作为亲双烯体和/或光反应。（±）-6结晶为由（2R，3R）和（2S，3S）对映异构体组成的外消旋化合物。

  DOI：

  10.1016/0040-4039(96)01672-3

文献信息

• Syntheses and properties of the nickel complexes of 1,2-dithiolates MEDT and PHDT. The crystal structure of [Bu4N][Ni(MEDT)2]
  作者：Yao Tian-Ming、Zuo Jing-Lin、You Xiao-Zeng、Xiao-Ying Huang

  DOI：10.1016/0277-5387(94)00409-8

  日期：1995.6

  The syntheses and characterizations of the nickel(III) complexes, [Bu(4)N] [Ni(MEDT)(2)] (MEDT = 5-methyl-6-hydro-1,4-dithiin-2,3-dithiolate) and [Bu(4)N] [Ni(PHDT)(2)] (PHDT = 5-phenyl-6-hydro-1,4-dithiin-2,3-dithiolate) are reported. Both complexes show characteristic IR and UV-vis absorptions of transition metal dithiolate complexes. The cyclic voltammograms contain two waves, indicating a two-step electrochemical process [ML(2)](0) = [ML(2)](1-) = [ML(2)](2-). The solid powder ESR spectra show three broad signals. The frozen glass ESR spectra yielded g value assignments of g(1) = 2.102, g(2) = 2.049 and g(3) = 2.004 for [Ni(MEDT)(2)](-) and g(1) = 2.104, g(2) = 2.048 and g(3) = 2.004 for [Ni(PHDT)(2)](-). Both complexes are semiconductors with electrical conductivities of the order of 10(-8) S cm(-1). Single-crystal structure analysis revealed that the gross geometry of the [NI(MEDT)(2)](-) anion is planar with the exception of the external unit-CH2CH(Me)-. There are two different kinds of anions. The anions form stacks along the b- and c-axes. The nearest intermolecular S-S distance is 5.104 Angstrom.
• Syntheses and characterization of heterobimetallic complexes (dppf)Pt(dithiolate) (dppf: bis(diphenylphosphino)ferrocene); X-ray crystal structures of (dppf)PtL where L=dmit, phdt and i-mnt
  作者：Dong-Youn Noh、Eun-Me Seo、Ha-Jin Lee、Hong-Young Jang、Moon-Gun Choi、Young Hwan Kim、Jongki Hong

  DOI：10.1016/s0277-5387(01)00783-5

  日期：2001.6

  Heterobimetallic complexes of the type (dppf)PtL (dppf = 1,1'-bis(diphenylphosphino)ferrocene; L = dmit (1,3-dithiole-2-thione-4,5-dithiolate), dddt (5,6-dihydro-1,4-dithiin-2,3-dithiolate), phdt (6-hydro-5-phenyl-1,4-dithiin-2,3-dithiolate), dphdt (5,6-diphenyl-1,4-dithiin-2,3-dithiolate), mtdt (1,2-bis(methylthio)ethylene-1,2-dithiolate), i-mnt (2,2-dicyano-1,1-ethylenedithiolate)) have been synthesized and studied by a high-resolution FAB-MS, cyclic voltammetry and P-31 NMR. (Dppf)Pt(i-mnt) exhibits one reversible redox peak at E-1/2 = 1.225 V and a strong Pt-P coupling constant (J(Pt-P) = 3237 Hz) due to the electron-accepting property of i-mnt ligand. On the contrary, (dppf)Pt(mtdt) shows three reversible redox peaks corresponding to [dppf](0/+) (E-1/2(1) = 0.470 V), [Pt(mtdt)(0/+) (E-1/2(2) = 1.050 V) and [Pt(mtdt)(+/2+) (E-1/2(3) = 1.405 V) processes and a weak Pt-P coupling constant (J(Pt-P) = 2962 Hz) due to relatively strong electron-donor property of mtdt ligand. X-ray structural analyses were performed for the three complexes: (dppf)PtL where L = dmit, phdt and i-mnt. The P2PtS2 core shows a distorted square planar geometry for the three complexes with P(1)-Pt-P(2) bite angle being larger than 96 degrees. The S(1)-Pt-S(2) bite angle of the i-mnt complex is the smallest (74.42 degrees) because of the formation of the four-membered ring. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Larsen, Sine; Thorsteinsson, Thorstein; Boewadt, Soeren, Acta Chemica Scandinavica, 1991, vol. 45, # 7, p. 709 - 715
  作者：Larsen, Sine、Thorsteinsson, Thorstein、Boewadt, Soeren、Hansen, Thomas K.、Varma, Karikath S.、et al.

  DOI：——

  日期：——
• Electrochemistry and strong near-IR absorption of the [Ni(dphdt)2]n complexes (n=−1, 0; dphdt=5,6-diphenyl-1,4-dithiin-2,3-dithiolate); X-ray crystal structure of (Ph4P)[Ni(dphdt)2](CH2Cl2)
  作者：Ha-Jin Lee、Dong-Youn Noh

  DOI：10.1016/s0277-5387(99)00379-4

  日期：2000.2

  Nickel bisdithiolene complexes C-x[Ni(dphdt)(2)] (x = 1 or 0.1, C = tetrabutylammonium (n-Bu4N+); x = 1, C = tetraphenylphosphonium (Ph4P+); dphdt=5,6-diphenyl-1,4-dithiin-2,3-dithiolate) have been synthesized and characterized. The molecular structure of (ph(4)P) [Ni(dphdt)(2)] (CH2CI2) was determined by X-ray analysis. Ni(S2C2S2)(2) core is planar and stacking along the c-axis and the shortest intra-stack S ... S distance is 4.529 Angstrom. According to the cyclic voltammetry of (n-Bu4N) [Ni(dphdt)(2)], two phenyl groups on the dphdt ligand decrease the electron density on the Ni(S2C2S2)(2) core and increase the oxidation potentials compared to those of the (n-Bu4N) [Ni(dddt)(2)] complex (dddt = 5,6-dihydro-1,4-dithiin-2,3-dithiolate). Near-IR spectra of the complexes show that phenyl substitution on the ligand does not give rise to the evident change in transition energy due to the lack of coplanarity with the Ni(S2C2S2)(2) core. (C) 2000 Elsevier Science Ltd All rights reserved.
• New synthesis of phenyl-substituted 2,3-dihydro-1,3-dithiolo[4,5-e][1,4]dithiin-6-thione
  作者：Dong-Youn Noh、Ha-Jin Lee、Jongki Hong、Allan E Underhill

  DOI：10.1016/0040-4039(96)01672-3

  日期：1996.10

  The facile synthesis of 4 and (±)-6 was carried out via a Diels-Alder type [2+4] cycloaddition reaction of oligomeric dien 8 with styrene or t-stilbene, respectively, as a dienophile by a thermal reaction and/or photoreaction. (±)-6 crystallized as a racemic compound composed of (2R,3R) and (2S,3S) enantiomers.

  的简便合成4和（±） - 6进行经由狄尔斯-阿尔德型[2 + 4]的低聚二烯的环加成反应8与苯乙烯或吨通过热反应分别芪，作为亲双烯体和/或光反应。（±）-6结晶为由（2R，3R）和（2S，3S）对映异构体组成的外消旋化合物。