methyl 3-hydroxy-3-(2-naphthyl)-2-propenedithioate | 1452531-19-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: methyl 3-hydroxy-3-(2-naphthyl)-2-propenedithioate
• 英文别名: (Z)-Methyl 3-hydroxy-3-(naphthalen-2-yl)prop-2-enedithioate；methyl 3-hydroxy-3-naphthalen-2-ylprop-2-enedithioate
• CAS: 1452531-19-9
• 化学式: C₁₄H₁₂OS₂
• 分子量: 260.381
• InChiKey: AWVCPCUQHAUWLP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.43
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  methyl 3-hydroxy-3-(2-naphthyl)-2-propenedithioate 在 四(三苯基膦)钯 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 30.0h， 以78%的产率得到5-ethylsulfanyl-4-(2-naphthoyl)-3-[1-(2-naphthyl)acetylidene]-3H-1,2-dithiole
  参考文献：
  名称：

  Palladium Catalyzed Oxidative Coupling of α-Enolic Dithioesters: A New Entry to 3,4,5-Trisubstituted 1,2-Dithioles via a Double Activation Strategy

  摘要：

  An operationally simple, facile, and convenient one-pot straightforward method for the construction of 3,4,5-trisubstituted 1,2-dithioles has been explored and developed via palladium catalyzed self-coupling of alpha-enolic dithioesters for the first time. Pd(0) efficiently catalyzes the activation and cleavage of S-H and C-S bonds to achieve cascade coupling, which results in the concomitant formation of new S-S and C-C bonds. Optimization data, substrate scope, and mechanistic insights are discussed.

  DOI：

  10.1021/ol402728y
• 作为产物：
  描述：

  三硫代碳酸二甲酯 、 2-萘乙酮 以 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 11.0h， 生成 methyl 3-hydroxy-3-(2-naphthyl)-2-propenedithioate
  参考文献：
  名称：

  新型方形平面杂原子阳离子配合物[Ni（II）β-氧代二硫酯-dppe] +的合成与表征 它们用作Chan-Lam偶联的催化剂

  摘要：

  新颖杂[镍（II）β-oxodithioester-DPPE] + PF 6 -复合物（β-oxodithioester =甲基-3-羟基-3-苄基-2- propenedithioate L1 1，2-甲基-3-羟基-3-（p -甲氧基苯基）-2-丙二硫代酸酯L2 2，甲基3-羟基-3-（萘基）-2-丙二硫代酸酯L3 3，甲基-3-羟基-3-（对氯苯基）-2-丙二硫代酸酯L4 4，甲基-3 -羟基-3-（对-溴苯基）-2-丙二硫醇酯L5 5和-3-羟基-3-（对-氰基苯基）-2-丙二硫醇酯L6 6）已通过元素（C，H，N）分析，ESI-MS，IR，紫外可见，1 H，13 C { 1 H}，31 P { 1 H}和19 F { 1 H}合成并表征NMR光谱。同晶阳离子络合物的扭曲的四方平面结构2，3，4和5已经通过X射线晶体学确定。研究了1-6的催化活性，涉及涉及芳基硼酸和胺的Chan-L

  DOI：

  10.1039/d0nj01139h

文献信息

• New planar <i>trans</i>-copper(II) β-dithioester chelate complexes: synthesis, characterization, anticancer activity and DNA-binding/cleavage studies
  作者：Manoj Kumar Yadav、Akhilendra Kumar Maurya、Gunjan Rajput、Krishna Kumar Manar、Manjula Vinayak、Michael G. B. Drew、Nanhai Singh

  DOI：10.1080/00958972.2016.1275589

  日期：2017.2.16

  spectra. The structures of HL3 and its corresponding complex 3 have been determined by X-ray crystallography. Electrochemical behavior of all complexes has been studied by cyclic voltammetry. All five planar complexes show efficient DNA-binding and DNA (PBR322)-cleavage in a concentration-dependent manner (1 > 3 > 5 > 2 > 4). Cleavage efficiency is enhanced in the presence of H2O2 as well as ascorbic acid

  摘要 新的平面反式铜 (II) β-二硫酯配合物，[Cu(L)2] (L = 甲基-3-羟基-(3-吡啶基)-2-亚丙基二硫酸酯 (L1 in 1)，甲基-3-羟基-(2-naphthyl)-2-propenedithioate (L2 in 2),methyl-3-hydroxy-3-(p-methoxyphenyl)-2-propenedithioate (L3 in 3),methyl-3-hydroxy-3-(p- fluorophenyl)-2-propenedithioate (L4 in 4), andmethyl-3-hydroxy-3-(p-bromophenyl)-2-propenedithioate (L5 in 5)), 已经合成并用元素 (C, H, N S) 分析、ESI-MS、IR 和 UV-vis 光谱。HL3 及其相应配合物 3 的结构已通过 X 射线晶体
• Impact of ligand substituents on the crystal structures, optical and conducting properties of phenylmercury(II) β-oxodithioester complexes
  作者：Kavita Kumari、Michael G.B. Drew、Nanhai Singh

  DOI：10.1016/j.jorganchem.2020.121532

  日期：2020.12

  New phenylmercury(II) complexes 1–5 with functionalized β-oxodithioester ligands, [PhHg(II) (β-oxodithioester)], β-oxodithioester = methyl-3-hydroxy-3-(4-pyridyl)-2-propenedithioate L1 1, methyl-3-hydroxy-3-(p-chlorophenyl)-2-propenedithioate L2 2, methyl-3-hydroxy-3-(naphthyl)-2-propenedithioate L3 3, methyl-3-hydroxy-3-(9-anthracenyl)-2-propenedithioate L4 4 and methyl-3-hydroxy-3-(p-fluoropheny

  新苯基汞（II）配合物1 - 5与官能β-oxodithioester配体，[PhHg（II）（β-oxodithioester）]，β-oxodithioester =甲基-3-羟基-3-（4-吡啶基）-2- propenedithioate L1 1，甲基-3-羟基-3-（p -氯苯基）-2- propenedithioate L2 2，甲基-3-羟基-3-（萘基）-2- propenedithioate L3 3，甲基-3-羟基-3-（9合成（蒽基）-2-丙二硫代酸酯L4 4和-3-羟基-3-（对氟苯基）-2-丙二硫代甲基酯L5 5，并通过元素（C，H，N）分析，IR，UV-Vis表征。，1 H和13 C 11 H NMR光谱。已经通过单晶X射线衍射研究了它们的结构。线性两坐标大约汞原子的几何形状，通过本位苯基的-C和由β-oxodithioester配体的S15原子被揭示在所有复合物。所有复合物中均存在分子内Hg
• Iron-Promoted Domino Annulation of α-Enolic Dithioesters with Ninhydrin under Solvent-Free Conditions: Chemoselective Direct Access to Indeno[1,2-<i>b</i>]thiophenes
  作者：Suvajit Koley、Sushobhan Chowdhury、Tanmoy Chanda、B. Janaki Ramulu、Ganesh Chandra Nandi、Maya Shankar Singh

  DOI：10.1002/ejoc.201402276

  日期：2014.9

  An efficient, straightforward, and highly chemoselective strategy has been devised for the synthesis of a broad range of indeno[1,2-b]thiophenes through the annulation of α-enolic dithioesters with ninhydrin under solvent-free conditions. The advantages of this nucleophilic domino substitution/cyclization sequence are highlighted by the use of inexpensive and readily available FeCl3·6H2O as the catalyst

  通过在无溶剂条件下将 α-烯醇二硫酯与茚三酮环化，设计了一种有效、直接且高度化学选择性的策略，用于合成广泛的茚并 [1,2-b] 噻吩。这种亲核多米诺取代/环化序列的优点通过使用廉价且容易获得的 FeCl3·6H2O 作为催化剂、操作简单、反应时间短、其官能团耐受性以及伴随形成 C- C 和 C-S 键在一次操作中得到一个噻吩环。该方法在步骤数量方面是经济的，并且是一种不含有毒试剂和溶剂的一锅式碳高效工艺。重要的是，一种新合成的茚[1,
• Site‐Specific S‐Allylation of α‐Enolic Dithioesters with Morita‐Baylis‐Hillman Acetates at Room Temperature: Precursor for Thiopyrans
  作者：Sonam Soni、Suvajit Koley、Monish A. Ansari、Maya Shankar Singh

  DOI：10.1002/adsc.201900580

  日期：2019.9.3

  An efficient one‐pot allylic alkylation of α‐enolic dithioesters (DTEs) with Morita‐Baylis‐Hillman (MBH) acetates has been devised in ethanol at room temperature. The reaction being site‐selective provided S‐allylated product exclusively with trace amount of C‐allylated one. Remarkably, some of the S‐allylated product undergoes [3,3]‐sigmatropic rearrangement to C‐allylated one under ethanol reflux

  室温下在乙醇中设计了一种有效的一锅法烯醇二硫代酯（DTE）与Morita-Baylis-Hillman（MBH）乙酸酯的烯丙基烷基化反应。现场选择性反应只为S-烯丙基化产物提供痕量的C-烯丙基化产物。值得注意的是，一些S-烯丙基化的产物在乙醇回流下经历了[3,3]-σ重排，变成C-烯丙基化的产物。该方案的典型特征是分离出S-烯丙基化的α-氧杂环丁烯二硫缩醛（一种三取代的烯烃），该化合物已被进一步用于合成硫吡喃。
• Synthesis of thiazolidin-4-ones from α-enolic dithioesters and α-halohydroxamates
  作者：Jianguo Sun、Taimin Wang、Xuecheng Zhu、Wei Xu、Bin Cheng、Hongbin Zhai

  DOI：10.1039/d1nj01970h

  日期：——

  A facile access to thiazolidin-4-ones from α-enolic dithioesters and α-halohydroxamates in situ derived active 1,3-dipolar aza-oxyallyl cations was achieved under mild conditions.

  从α-烯醇二硫酯和α-卤代羟羟酸酯原位衍生的活性1,3-偶极氧化烯丙基阳离子，在温和条件下成功地合成了噻唑啉-4-酮。