dioxolanne de l'α-phenylthioacetaldehyde | 179669-44-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: dioxolanne de l'α-phenylthioacetaldehyde
• 英文别名: 2-((phenylthio)methyl)-1,3-dioxolane；2-(Phenylsulfanylmethyl)-1,3-dioxolane
• CAS: 179669-44-4
• 化学式: C₁₀H₁₂O₂S
• 分子量: 196.27
• InChiKey: WKLHBMAQBPQOKU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  43.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  dioxolanne de l'α-phenylthioacetaldehyde 在 甲酸 、 3 A molecular sieve 、 叔丁基锂 作用下， 以 乙醚 为溶剂， 反应 4.5h， 生成 4-[(E)-2-phenylsulfanylprop-1-enyl]morpholine
  参考文献：
  名称：

  Duhamel, Lucette; Chauvin, Joe; Messier, Angela, Journal of Chemical Research, Miniprint, 1982, # 2, p. 621 - 640

  摘要：

  DOI：
• 作为产物：
  描述：

  2-溴甲基-1,3-二氧戊烷 、 苯硫酚 在 三乙胺 作用下， 反应 24.0h， 以77%的产率得到dioxolanne de l'α-phenylthioacetaldehyde
  参考文献：
  名称：

  Duhamel, Lucette; Chauvin, Joe; Messier, Angela, Journal of Chemical Research, Miniprint, 1982, # 2, p. 621 - 640

  摘要：

  DOI：

文献信息

• Nickel-Catalyzed C–S Reductive Cross-Coupling of Alkyl Halides with Arylthiosilanes toward Alkyl Aryl Thioethers
  作者：Yu-Zhong Yang、Yang Li、Gui-Fen Lv、De-Liang He、Jin-Heng Li

  DOI：10.1021/acs.orglett.2c01954

  日期：2022.7.22

  A nickel-catalyzed C–S reductive cross-coupling of alkyl halides with arylthiosilanes for producing alkyl aryl thioethers is developed. This reaction is initiated by umpolung transformations of arylthiosilanes followed by C–S reductive cross-coupling with alkyl halides to manage an electrophilic alkyl group onto the electrophilic sulfur atom and then construct a C(sp3)–S bond, and features exquisite

  开发了一种镍催化的烷基卤化物与芳基硫硅烷的 C-S 还原交叉偶联，用于生产烷基芳基硫醚。该反应由芳基硫硅烷的 umpolung 转变引发，然后与卤代烷发生 C-S 还原交叉偶联，将亲电烷基控制在亲电硫原子上，然后构建 C(sp 3 )-S 键，具有出色的化学选择性，对多种官能团具有优异的耐受性，并广泛应用于生物相关分子的后期修饰。
• Nickel‐catalyzed umpolung C S radical reductive cross coupling of S‐(trifluoromethyl)arylsulfonothioates with alkyl halides
  作者：Yu-Zhong Yang、Gui-Fen Lv、Ming Hu、Yang Li、Jin-Heng Li

  DOI：10.1016/j.cclet.2023.108590

  日期：2023.11

  A new cooperative nickel reductive catalysis and N,N-dimethylformamide-mediated strategy for umpolung CS radical reductive cross coupling of S-(trifluoromethyl)arylsulfonothioates with alkyl halides to produce alkyl aryl thioethers is described. This reaction features excellent selectivity, wide functionality tolerance, broad substrate scope, and facile late-stage modification of biologically relevant

  描述了一种新的协同镍还原催化和N,N-二甲基甲酰胺介导的策略，用于S- (三氟甲基)芳基硫代磺酸酯与烷基卤的 C S 自由基还原交叉偶联生产烷基芳基硫醚。该反应具有优异的选择性、广泛的功能耐受性、广泛的底物范围以及易于对生物相关分子进行后期修饰。机理研究认识到，通过用 Sn 热诱导 DMF还原，最初生成酰胺自由基阴离子，然后进行反极化还原和亲核磺酰基部分的单电子转移，形成巯基自由基并与 Ni 0 /Ni I /Ni III接合/Ni I催化循环。
• Synthesis and Cycloaddition Reactions of 1-(Arylthio)-1,3-dienes. A Combined Experimental and Theoretical Study of Bicyclic Adducts Structures
  作者：Jacques Maddaluno、Odile Gaonac'h、Albert Marcual、Loïc Toupet、Claude Giessner-Prettre

  DOI：10.1021/jo9519120

  日期：1996.1.1

  A method giving simple access to various 1-(phenylthio)-4-substituted-1,3-dienes (5-10) is described. The influence of the different functionalizations introduced on the dienic systems has been tested in a set of classical [4 + 2] cycloaddition reactions. Both the endo/exo and regio selectivities have been investigated. While the endo compound is, as expected, the only or major isomer in all cases, the regio competition between sulfur and oxygen is in favor of the oxygen substituent in the case studied here, in contrast to related works. For one type of adduct, X-ray crystallographic analysis and NMR spectroscopy have been used in conjunction with ab initio and semiempirical AM1 calculations to determine the structure and conformations of products as well as the energetic pathway from the primary concave endo cycloadduct (28) to a rearranged bicyclic structure (39), The theoretical results fully support the occurrence of a photochemical [1,3] sigmatropic shift of the thiophenyl group.
• DUHAMEL, L.;CHAUVIN, J.;MESSIER, A., J. CHEM. RES. MICROFICHE, 1982, N 2, 48-49
  作者：DUHAMEL, L.、CHAUVIN, J.、MESSIER, A.

  DOI：——

  日期：——
• Duhamel, Lucette; Chauvin, Joe; Messier, Angela, Journal of Chemical Research, Miniprint, 1982, # 2, p. 621 - 640
  作者：Duhamel, Lucette、Chauvin, Joe、Messier, Angela

  DOI：——

  日期：——