benzyl 3-hydroxy-3-phenylprop-2-enedithioate | 1428878-83-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: benzyl 3-hydroxy-3-phenylprop-2-enedithioate
• CAS: 1428878-83-4
• 化学式: C₁₆H₁₄OS₂
• 分子量: 286.419
• InChiKey: BJZCQWFHCGBPGI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.85
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  benzyl 3-hydroxy-3-phenylprop-2-enedithioate 在 溶剂黄146 、 sodium nitrite 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 生成 2-hydroxyimino-3-oxo-3-phenyl-dithiopropionic acid benzyl ester
  参考文献：
  名称：

  通过一锅中的亚硝化/还原/重氮化/环化级联反应从α-烯丙基二硫代酯轻松而直接地合成1,2,3-噻二唑

  摘要：

  通过一锅中通过级联1 –形成亚硝化/还原/重氮化/环化的顺序，可以从α-烯丙基二硫代酯中合成出操作简单，经济，直接的多种4,5-二取代的1,2,3-噻二唑。 2（N–S）和3–4（C–N）键。重要的是，这是来自二硫代酯的高度官能化的1,2,3-噻二唑的第一个直接方法。

  DOI：

  10.1016/j.tetlet.2014.02.115

文献信息

• 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。
• Eco-efficient, regioselective and rapid access to 4,5-disubstituted 1,2,3-thiadiazoles via [3 + 2] cycloaddition of α-enolicdithioesters with tosyl azide under solvent-free conditions
  作者：Maya Shankar Singh、Anugula Nagaraju、Girijesh Kumar Verma、Gaurav Shukla、Rajiv Kumar Verma、Abhijeet Srivastava、Keshav Raghuvanshi

  DOI：10.1039/c3gc37047j

  日期：——

  An efficient, sustainable, and regioselective one-pot synthesis of hitherto unreported 4-aroyl/hetaroyl/alkanoyl-5-alkyl/allyl/benzylsulfanyl-1,2,3-thiadiazoles has been achieved by [3 + 2] cycloaddition of α-enolicdithioesters with tosyl azide through cascade 1–2 (S–N) and 3–4 (C–N) bond connections involving Wolff-type heterocyclization. Optimally, the reactions are very fast and completed within 2–15 minutes, when a mixture of α-enolicdithioester and tosyl azide was stirred at 0 °C in the presence of Et3N under solvent-free conditions. Furthermore, no co-catalyst or activator is necessary. The eco-compatibility, mild conditions, excellent yields, easy purification, and avoidance of expensive/toxic reagents are advantages of this protocol to access this medicinally privileged substructure.

  通过 α 的 [3 + 2] 环加成，实现了迄今为止未报道的 4-芳酰基/杂酰基/烷酰基-5-烷基/烯丙基/苄基硫基-1,2,3-噻二唑的高效、可持续和区域选择性一锅法合成-烯醇二硫酯与甲苯磺酰叠氮通过级联 1–2 (S–N) 和 3–4 (C–N) 键连接，涉及 Wolff 型杂环化。最理想的是，当α-烯醇二硫酯和甲苯磺酰叠氮化物的混合物在无溶剂条件下、Et3N存在下于0℃搅拌时，反应非常快并在2-15分钟内完成。此外，不需要助催化剂或活化剂。生态相容性、温和的条件、优异的产量、易于纯化和避免昂贵/有毒试剂是该协议获得这种医学上特权子结构的优点。
• Magnesium catalyzed [3 + 3] heteroannulation of α-enolic dithioesters with MBH acetate: access to functionalized 3,4-dihydro-2<i>H</i>-thiopyrans
  作者：Sonam Soni、Gaurav Shukla、Maya Shankar Singh

  DOI：10.1039/d2ob01258h

  日期：——

  An efficient heteroannulation employing racemic Morita–Baylis–Hillman acetate and α-enolic dithioesters enabling the formation of dihydro-2H-thiopyrans is reported.

  报道了一种高效的杂环化反应，利用外消旋Morita-Baylis-Hillman乙酸酯和α-烯醇二硫代酯，实现了二氢-2H-硫吡喃的形成。
• Synthesis of 4‐(Trifluoromethyl)‐2,3‐Dihydrothiazoles from α‐Enolic Dithioesters and Imidoyl Sulfoxonium Ylides
  作者：Dezhi Yang、Yan Wang、Taimin Wang、Qian Dou、Kang Zhou、Hongbin Zhai、Bin Cheng

  DOI：10.1002/adsc.202201050

  日期：2023.1.10

  The synthesis of 4-(trifluoromethyl)-2,3-dihydrothiazoles from α-enolic dithioesters and imidoyl sulfoxonium ylides has been achieved under thermal conditions. This transformation is catalyst-free, additive-free, and operationally simple, and it proceeds via a formal insertion of alkenyl S−H generated in situ from dithioesters into ylides followed by an intramolecular annulation. This approach further

  4-(三氟甲基)-2,3-二氢噻唑从 α-烯醇二硫酯和亚氨基亚砜叶立德的合成已在热条件下实现。这种转化无需催化剂、无添加剂且操作简单，它通过将二硫酯原位生成的烯基 S−H 正式插入到叶立德中，然后进行分子内环化来进行。该方法进一步扩展了氟化亚胺酰亚砜叶立德和 α-烯醇二硫酯的两种多功能含硫结构单元的合成应用。