allyl dithiobenzoate | 27249-64-5

• 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: allyl dithiobenzoate
• 英文别名: Thiobenzoesaeure-allylthioester；Prop-2-en-1-yl benzenecarbodithioate；prop-2-enyl benzenecarbodithioate
• CAS: 27249-64-5
• 化学式: C₁₀H₁₀S₂
• 分子量: 194.321
• InChiKey: SMIYHRRYIKUWCD-UHFFFAOYSA-N

物化性质

• 沸点：
  159-161 °C(Press: 4 Torr)
• 密度：
  1.136±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  57.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  allyl dithiobenzoate 在 间氯过氧苯甲酸 作用下， 生成 Phenyl(allylthio)sulfine
  参考文献：
  名称：

  Intramolecular cyclization of (allylthio)sulfines via their vinylsulfenic acid tautomers.

  摘要：

  Intramolecular cyclization of enethiolizable (allylthio)sulfines afford 2-alkylidene-1,3-dithiolane-1-oxides in good yields. The formation of these compounds can be explained by an initial tautomerization of the sulfine to vinyl sulfenic acid, followed by an intramolecular addition of the sulfenic acid to the allylic double bond. The structures of the products were elucidated by means of H-1-and C-13-NMR spectroscopy as well as LIS effects, deuteriation experiments and an X-my analysis.

  DOI：

  10.1016/s0040-4039(00)60979-6
• 作为产物：
  描述：

  dithiobenzoic acid sodium salt 以72%的产率得到
  参考文献：
  名称：

  DROZD V. N.; POPOVA O. A., ZH. ORGAN. XIMII, 1980, 16, HO 10, 2047-2054

  摘要：

  DOI：

文献信息

• Thiophilic allylation of dithioesters and trithiocarbonates
  作者：Antonella Capperucci、Alessandro Degl'Innocenti、M.Cristiana Ferrara、Bianca F. Bonini、Germana Mazzanti、Paolo Zani、Alfredo Ricci

  DOI：10.1016/0040-4039(94)88190-1

  日期：1994.1

  Reaction of dithioesters and trithiocarbonates with silylated nucleophiles under fluoride ion conditions affords a novel example of silyl mediated regiochemical control in the thiophilic functionalization.

  二硫代酸酯和三硫代碳酸酯与甲硅烷基化的亲核试剂在氟离子条件下的反应提供了甲硅烷基介导的亲硫基官能化区域化学控制的新实例。
• Preparation of dithioesters by ester interchange and the PMR spectral properties of these compounds
  作者：N.H. Leon、R.S. Asquith

  DOI：10.1016/s0040-4020(01)93022-4

  日期：1970.1

  Aromatic and aliphatic dithioesters, many of them new, have been easily synthesized in excellent yields by the ester interchange reaction between carboxymethyl dithioesters and mercaptans. PMR spectra of these dithioesters and the corresponding oxygen analogues show that a strong anisotropic deshielding effect is associated with the highly polarized thiocarbonyl group.

  通过羧甲基二硫代酯与硫醇的酯交换反应，可以容易地以优异的产率合成芳族和脂肪族二硫代酯，其中许多是新的。这些二硫代酸酯和相应的氧类似物的PMR光谱表明，强极化的各向异性屏蔽作用与高度极化的硫代羰基有关。
• Single-electron transfer upon formation of 2,2,3,3-tetracyano-1-phenyl-7,8-dithiabicyclo[3.2.1]octane from allyl dithiobenzoate and tetracyanoethylene. Electrochemical investigations
  作者：K. P. Butin、A. A. Moiseeva、R. D. Rakhimov、I. V. Magedov

  DOI：10.1007/bf02494404

  日期：1999.1

  reaction of the TCNE.− radical anion with the PhSSAll.+ radical cation to form phenyl-substituted 2,2,3,3-tetracyano-7,8-dithiabicyclo[3.2.1]octane. When current is not applied, the reaction does not proceed at 20°C for 3 days. However, this reaction in boiling MeCN occurs without electrochemical activation and, apparently, involves intermediate formation of the above radical ions. It was established

  通过从 0.2 到 1.9 V 的循环电位扫描方法的研究提供了电分析证据，表明二硫代苯甲酸烯丙酯与四氰基乙烯 (TCNE) 在 MeCN 中的反应是随着 TCNE.- 自由基阴离子与 PhSSAll.+ 自由基阳离子反应形成苯基而进行的-取代的 2,2,3,3-四氰基-7,8-二硫杂双环[3.2.1]辛烷。当不施加电流时，反应不会在 20°C 下进行 3 天。然而，在沸腾的 MeCN 中发生的这种反应没有电化学活化，并且显然涉及上述自由基离子的中间形成。通过半经验 PM3 计算确定，二硫代苯甲酸烯丙酯和 TCNE 在化学电子转移之前形成稳定的电荷转移复合物。
• The reaction of allylic esters of dithiocarboxylic acids with tetracyanoethylene affording 3,3,4,4-tetracyano-6,8-dithiabicyclo[3.2.1]octanes
  作者：Igor V. Magedov、Sergey Yu. Shapakin、Victor N. Drozd

  DOI：10.1016/0040-4020(95)00739-u

  日期：1995.10

  A range of substituted 3,3,4,4-tetracyano-6,8-dithiabicyclo[3.2.1]octanes, viz. compounds 5dg, 5j–m, and 5o–u, have been synthesized from the corresponding allyl dithiocarboxylates by a cation radical cycloaddition reaction, using tetracyanoethylene 2 in acetonitrile. The reaction scope has been studied and the mechanism proposed on the basis of the dithioester's chemical behaviour in respect to oxidizing

  一系列取代的3,3,4,4-四氰基-6,8-二硫代双环[3.2.1]辛烷，即。使用四氰基乙烯2在乙腈中，通过阳离子自由基加成反应，从相应的二硫代烯丙基羧酸烯丙基酯合成了化合物5dg，5j-m和5o-u。根据二硫代酯相对于氧化剂的化学行为，质谱数据，取代基效应分析以及采用MINDO / 3方法的UHF方法进行量子化学计算，研究了反应范围并提出了机理。
• Drozd, V. N.; Popova, O. A., Journal of Organic Chemistry USSR (English Translation), 1983, vol. 19, # 5, p. 946 - 949
  作者：Drozd, V. N.、Popova, O. A.

  DOI：——

  日期：——