Dimethyl 2-(1,3-dithiol-2-ylidene)-1,3-dithiole-4,5-dicarboxylate | 106206-93-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Dimethyl 2-(1,3-dithiol-2-ylidene)-1,3-dithiole-4,5-dicarboxylate
• CAS: 106206-93-3
• 化学式: C₁₀H₈O₄S₄
• 分子量: 320.435
• InChiKey: FDYJXNIODJRMRX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  154
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Dimethyl 2-(1,3-dithiol-2-ylidene)-1,3-dithiole-4,5-dicarboxylate 在 sodium tetrahydroborate 、 三苯基膦 、 zinc(II) chloride 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 生成 2,3-bis(acetylthiomethyl)tetrathiafulvalene
  参考文献：
  名称：

  Solid-State Transformations of Zinc 1,4-Benzenedicarboxylates Mediated by Hydrogen-Bond-Forming Molecules

  摘要：

  The zinc 1,4-benzenedicarboxylates [Zn3(bdc)3(H2O)3] . 4 DMF (1; bdc = 1,4-benzenedicarboxylate), [Zn(bdc)(H2O)] . DMF (2), and [Zn(bdc)] DMF (3) crystallise at room temperature from mixtures of toluene/ dimethylformamide (DMF) under concentrated, dilute and dry conditions, respectively. The structure of phase 1 (monoclinic: P2(1)/c, a 13.065(1), b = 9.661(1), c = 18.456(1) A, beta = 106.868(2) degrees) consists of layers containing stacks of three zinc cations linked by mono- and bidentate bdc groups. Structure 1 converts to the known phase 2 by an irreversible, reconstructive phase transformation, whereas 2 and 3 interconvert reversibly upon the loss or addition of water. Removal of all solvent molecules included during crystallisation gives poorly crystalline [Zn(bdc)] (4), which is readily converted to highly crystalline solids upon contact with hydrogen-bond-forming molecules such as water, DMF and small alcohols. The crystal structures of the mono- and dihydrates [Zn(bdc)(H2O)] (6) and [Zn(bdc)-(H2O)2] (7) have been determined ab initio from powder X-ray diffraction data (compound 6, monoclinic: C2/c, a = 17.979(1), b = 6.352(1), c = 7.257(1) A, beta=91.477(1) compound 7, monoclinic: C2/c, a = 14.992(1), b = 5.0303(2), c = 12.098(1) A, beta = 103.82(1) degrees). The methanol adduct [Zn3(bdc)3] . 6CH3OH (5) is the same as that prepared previously by direct crystallisation. Comparison of these adduct structures with those prepared directly reveal that they are formed by in situ recrystallisations. Subsequent removal of included molecules gives amorphous [Zn(bdc)], which can be recrystallised again when placed in contact with hydrogen-bond-forming molecules.

  DOI：

  10.1002/1521-3765(20011203)7:23<5168::aid-chem5168>3.0.co;2-s
• 作为产物：
  描述：

  (1R,2R,6S,7S)-4-(4,5-Bis-methoxycarbonyl-[1,3]dithiol-2-ylidene)-3,5-dithia-tricyclo[5.2.1.0^2,6]dec-8-ene-8,9-dicarboxylic acid dimethyl ester 600.0 ℃ 、1.33 Pa 条件下， 以73%的产率得到Dimethyl 2-(1,3-dithiol-2-ylidene)-1,3-dithiole-4,5-dicarboxylate
  参考文献：
  名称：

  单和双取代四硫富瓦烯的不寻常直接合成

  摘要：

  除双加合物4外，降冰片二烯，三丁基膦，二硫化碳和炔属二酯的直接反应提供了降冰片烯稠合的二氢四硫富富瓦烯7，并且对于反应性较低的炔属双极性亲和剂仅分离出7。在快速真空热解后，化合物7进行逆狄尔斯-阿尔德反应，得到取代的四硫富瓦烯8。通过使用降冰片二烯二酯代替降冰片二烯和DMAD，可以更高的总产率获得8a。尝试分离两性离子结构9给出了具有新颖的1,2,5-三噻吩稳定的内酯结构11的重排产物。。

  DOI：

  10.1016/s0040-4039(99)80112-9

文献信息

• Solid-State Transformations of Zinc 1,4-Benzenedicarboxylates Mediated by Hydrogen-Bond-Forming Molecules
  作者：Mark Edgar、Robert Mitchell、Alexandra M. Z. Slawin、Philip Lightfoot、Paul A. Wright

  DOI：10.1002/1521-3765(20011203)7:23<5168::aid-chem5168>3.0.co;2-s

  日期：2001.12.3

  The zinc 1,4-benzenedicarboxylates [Zn3(bdc)3(H2O)3] . 4 DMF (1; bdc = 1,4-benzenedicarboxylate), [Zn(bdc)(H2O)] . DMF (2), and [Zn(bdc)] DMF (3) crystallise at room temperature from mixtures of toluene/ dimethylformamide (DMF) under concentrated, dilute and dry conditions, respectively. The structure of phase 1 (monoclinic: P2(1)/c, a 13.065(1), b = 9.661(1), c = 18.456(1) A, beta = 106.868(2) degrees) consists of layers containing stacks of three zinc cations linked by mono- and bidentate bdc groups. Structure 1 converts to the known phase 2 by an irreversible, reconstructive phase transformation, whereas 2 and 3 interconvert reversibly upon the loss or addition of water. Removal of all solvent molecules included during crystallisation gives poorly crystalline [Zn(bdc)] (4), which is readily converted to highly crystalline solids upon contact with hydrogen-bond-forming molecules such as water, DMF and small alcohols. The crystal structures of the mono- and dihydrates [Zn(bdc)(H2O)] (6) and [Zn(bdc)-(H2O)2] (7) have been determined ab initio from powder X-ray diffraction data (compound 6, monoclinic: C2/c, a = 17.979(1), b = 6.352(1), c = 7.257(1) A, beta=91.477(1) compound 7, monoclinic: C2/c, a = 14.992(1), b = 5.0303(2), c = 12.098(1) A, beta = 103.82(1) degrees). The methanol adduct [Zn3(bdc)3] . 6CH3OH (5) is the same as that prepared previously by direct crystallisation. Comparison of these adduct structures with those prepared directly reveal that they are formed by in situ recrystallisations. Subsequent removal of included molecules gives amorphous [Zn(bdc)], which can be recrystallised again when placed in contact with hydrogen-bond-forming molecules.
• Unusually direct synthesis of mono- and di-substituted tetrathiafulvalenes
  作者：R.Alan Aitken、Lawrence Hill、Neil J Wilson

  DOI：10.1016/s0040-4039(99)80112-9

  日期：1999.1

  Direct reaction of norbornadiene, tributylphosphine, carbon disulfide and acetylenic diesters affords the norbornene-fused dihydrotetrathiafulvalenes 7 in addition to the bis-adducts 4 and for less reactive acetylenic dipolarophiles only 7 is isolated. Upon flash vacuum pyrolysis the compounds 7 undergo a retro Diels-Alder reaction to give substituted tetrathiafulvalenes 8. By using the norbornadiene

  除双加合物4外，降冰片二烯，三丁基膦，二硫化碳和炔属二酯的直接反应提供了降冰片烯稠合的二氢四硫富富瓦烯7，并且对于反应性较低的炔属双极性亲和剂仅分离出7。在快速真空热解后，化合物7进行逆狄尔斯-阿尔德反应，得到取代的四硫富瓦烯8。通过使用降冰片二烯二酯代替降冰片二烯和DMAD，可以更高的总产率获得8a。尝试分离两性离子结构9给出了具有新颖的1,2,5-三噻吩稳定的内酯结构11的重排产物。。