2-phenyl-1,3-propanedithiol | 25636-61-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-phenyl-1,3-propanedithiol
• 英文别名: 2-Phenyl-1,3-propandithiol；2-phenylpropane-1,3-dithiol
• CAS: 25636-61-7
• 化学式: C₉H₁₂S₂
• 分子量: 184.326
• InChiKey: KLVCOXYYQMXTCN-UHFFFAOYSA-N

物化性质

• 沸点：
  293.0±33.0 °C(Predicted)
• 密度：
  1.099±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-phenyl-1,3-propanedithiol 在 trimethylamine-N-oxide dihydrate 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 3.0h， 生成 [μ-(SCH₂)₂CHC₆H₅]Fe₂(CO)₅(κ-dppm)
  参考文献：
  名称：

  Synthesis, characterization and electrochemistry of phenyl-functionalized diiron propanedithiolate complexes

  摘要：

  A dinuclear [2Fe2S] mimic, [mu-(SCH2)(2)CHC6H5]Fe-2(CO)6 (1), of the active site of FeFe-hydrogenases has been synthesized from the reaction of 2-phenyl-1,3-propanedithiol with Fe-3(CO)(12). Displacement one or two carbonyls of complex I with triphenylphosphine (PPh3) or bis(diphenylphosphino)methane (dppm) yielded [mu-(SCH2)(2)CHC6H5]Fe-2(CO)(5)(PPh3) (2), [mu-(SCH2)(2)CHC6H5]Fe-2(CO)(5)(kappa-dPPm) (3) and [mu-(SCH2)(2)CHC6H5]Fe-2(CO)(4)(mu-dPPm) (4). Complexes 1-4 have been fully characterized by elemental analysis, mass spectrometry, IR, H-1, C-13 and P-31 NMR spectroscopic techniques, and unequivocally determined by single crystal X-ray diffraction analysis. The phenyl groups are attached directly to the bridgehead-C atoms of the propanedithiolate bridge via equatorial bonds in chair conformation six-membered rings. The electrochemical behavior of 1-4 and the reduction of the proton of CF3COOH to hydrogen, catalyzed by 1 and 3, were investigated by cyclic voltammetry. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2013.09.027
• 作为产物：
  描述：

  2-苯基-1,3-丙二醇 在 三甲胺盐酸盐 、 三乙胺 、 硫脲 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 5.0h， 生成 2-phenyl-1,3-propanedithiol
  参考文献：
  名称：

  Facile deprotection of dithioacetals by using a novel 1,4-benzoquinone/cat. NaI system

  摘要：

  The combination of 1,4-benzoquinone and a catalytic amount of NaI was found to be effective for the deprotection of dithioacetals. The reactions proceeded efficiently under mild, near-neutral reaction conditions, producing a wide range of aryl and alkyl aldehydes and ketones generally in high yields with good functional group compatibility. The method developed therefore represents a general, facile, and highly applicable approach for deprotecting dithioacetals. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.08.061

文献信息

• Carbon–Carbon Bond Cleavage in Fluorescent Pyronin Analogues Induced by Yellow Light
  作者：Peter Štacko、Peter Šebej、Aneesh Tazhe Veetil、Petr Klán

  DOI：10.1021/ol302244f

  日期：2012.9.21

  A novel class of pyronin analogues, which undergoes a photochemically induced cleavage of the C-C bond in the presence of water in both solution and on a silica gel surface upon direct irradiation with visible fight, is reported. The reaction course can be monitored by characteristic fluorescence of both the starting compound and the final product. This system could find useful applications in the field of photoremovable protecting groups or caged fluorophores.
• Salim, A.; Tillett, J. G., Phosphorus, Sulfur and Silicon and the Related Elements, 1991, vol. 60, # 3/4, p. 215 - 222
  作者：Salim, A.、Tillett, J. G.

  DOI：——

  日期：——
• Novel heterocyclic pesticidal compounds
  申请人：THE WELLCOME FOUNDATION LIMITED

  公开号：EP0294228B1

  公开（公告）日：1992-08-26
• Facile deprotection of dithioacetals by using a novel 1,4-benzoquinone/cat. NaI system
  作者：Kiyofumi Inamoto、Tetsuya Yamada、Sei-ichi Kato、Shoko Kikkawa、Yoshinori Kondo

  DOI：10.1016/j.tet.2013.08.061

  日期：2013.11

  The combination of 1,4-benzoquinone and a catalytic amount of NaI was found to be effective for the deprotection of dithioacetals. The reactions proceeded efficiently under mild, near-neutral reaction conditions, producing a wide range of aryl and alkyl aldehydes and ketones generally in high yields with good functional group compatibility. The method developed therefore represents a general, facile, and highly applicable approach for deprotecting dithioacetals. (C) 2013 Elsevier Ltd. All rights reserved.
• Synthesis, characterization and electrochemistry of phenyl-functionalized diiron propanedithiolate complexes
  作者：Chang-Gong Li、Yong Zhu、Xing-Xing Jiao、Xiao-Qin Fu

  DOI：10.1016/j.poly.2013.09.027

  日期：2014.1

  A dinuclear [2Fe2S] mimic, [mu-(SCH2)(2)CHC6H5]Fe-2(CO)6 (1), of the active site of FeFe-hydrogenases has been synthesized from the reaction of 2-phenyl-1,3-propanedithiol with Fe-3(CO)(12). Displacement one or two carbonyls of complex I with triphenylphosphine (PPh3) or bis(diphenylphosphino)methane (dppm) yielded [mu-(SCH2)(2)CHC6H5]Fe-2(CO)(5)(PPh3) (2), [mu-(SCH2)(2)CHC6H5]Fe-2(CO)(5)(kappa-dPPm) (3) and [mu-(SCH2)(2)CHC6H5]Fe-2(CO)(4)(mu-dPPm) (4). Complexes 1-4 have been fully characterized by elemental analysis, mass spectrometry, IR, H-1, C-13 and P-31 NMR spectroscopic techniques, and unequivocally determined by single crystal X-ray diffraction analysis. The phenyl groups are attached directly to the bridgehead-C atoms of the propanedithiolate bridge via equatorial bonds in chair conformation six-membered rings. The electrochemical behavior of 1-4 and the reduction of the proton of CF3COOH to hydrogen, catalyzed by 1 and 3, were investigated by cyclic voltammetry. (C) 2013 Elsevier Ltd. All rights reserved.