methyl 3-hydroxy-4,4-dimethylpent-2-enedithioate | 1428878-71-0

• 分子结构分类: 有机化合物 - 有机硫化合物
• 英文名称: methyl 3-hydroxy-4,4-dimethylpent-2-enedithioate
• CAS: 1428878-71-0
• 化学式: C₈H₁₄OS₂
• 分子量: 190.331
• InChiKey: SSENYVIVIPHWHD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.16
• 重原子数：
  11.0
• 可旋转键数：
  1.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 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-4,4-dimethylpent-2-enedithioate 在 N-氯代丁二酰亚胺 作用下， 以 二甲基亚砜 为溶剂， 反应 0.17h， 以83%的产率得到dimethyl 2,3-dipivaloylbutanebis(dithioate)
  参考文献：
  名称：

  室温下α-烯丙基二硫酯的无金属试剂依赖性SS和CC均偶联：通过化学选择性Paal-Knorr方法直接获得完全取代的对称噻吩

  摘要：

  AbstractAn unprecedented metal‐free oxidative homodimerization of α‐enolic dithioesters has been achieved for the first time at room temperature within 5–10 min. Molecular iodine promotes the SS coupling leading to S,S′‐bis(dithioacetals), while N‐chlorosuccinimide facilitates CC coupling to give α,α′‐bis(β‐oxo dithioesters) in good to excellent yields. Furthermore, the newly generated α,α′‐bis(β‐oxo dithioesters) have been directly employed in the synthesis of fully substituted thiophenes with a unique symmetrical substitution pattern in a one‐pot, two‐step reaction sequence.magnified image

  DOI：

  10.1002/adsc.201400828

文献信息

• 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。
• Catalyst-free one-pot four-component domino reactions in water–PEG-400: highly efficient and convergent approach to thiazoloquinoline scaffolds
  作者：Anugula Nagaraju、B. Janaki Ramulu、Gaurav Shukla、Abhijeet Srivastava、Girijesh Kumar Verma、Keshav Raghuvanshi、Maya Shankar Singh

  DOI：10.1039/c4gc01431f

  日期：——

  Catalyst-free one-pot sustainable synthesis of thiazoloquinoline and thiazolopyridine scaffolds is achievedviafour-component domino reactions in water–PEG.

  无催化剂的一锅法可持续合成噻唑喹啉和噻唑吡啶骨架，通过在水-PEG中进行四组分多米诺反应实现。
• DMAP mediated one-pot domino thienannulation: a versatile, regioselective and green mechanochemical route to naphtho[2,3-b]thiophenes
  作者：Gaurav Shukla、Girijesh Kumar Verma、Anugula Nagaraju、Rajiv Kumar Verma、Keshav Raghuvanshi、Maya Shankar Singh

  DOI：10.1039/c3ra41100a

  日期：——

  Solvent-free mechanochemical route to naphtho[2,3-b]thiophenes via [3 + 2] oxidative heteroannulation of α-enolicdithioesters and β-oxothioamides with 1,4-naphthoquinone has been achieved at room temperature.

  在室温下，通过 α-烯醇二硫酯和 β-硫代酰胺与 1,4-萘醌的 [3 + 2] 氧化杂环化，实现了无溶剂机械化学路线制备萘并[2,3-b]噻吩。