(3-methoxyprop-1-ynyl)-p-tolyl sulfide | 181716-27-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (3-methoxyprop-1-ynyl)-p-tolyl sulfide
• 英文别名: 1-(3-Methoxyprop-1-ynylsulfanyl)-4-methylbenzene；1-(3-methoxyprop-1-ynylsulfanyl)-4-methylbenzene
• CAS: 181716-27-8
• 化学式: C₁₁H₁₂OS
• 分子量: 192.282
• InChiKey: WXFSGCVXUYUEOH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  34.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3-methoxyprop-1-ynyl)-p-tolyl sulfide 在 oxidating agent 作用下， 以78%的产率得到(+/-)-3-methoxypropynyl p-tolyl sulfoxide
  参考文献：
  名称：

  Ni（0）促进的烯丙基卤化物和乙炔的环羰基化反应中的环戊烯酮的不对称方法

  摘要：

  报道了通过Ni（CO）4促进的炔-烯丙基卤化物环化-羰基化来不对称合成环戊烯酮的不同方法。乙炔亚砜1的使用已证明对合成无环，稠合[5 + 8]和螺[5 + 5]，[5 + 7]和[5 + 8]环戊烯有效，而芳基亚砜的放置烯丙基体系上的环糊精无法提供任何环加合物。通过这种方法已经获得了手性稠合的[5 + 8]，螺[5 + 7]和[5 + 8]环戊烯酮。最后，当在我们的反应体系中使用不同的同手性α-取代的羧酸盐作为配体时，观察到适度的对映选择性。

  DOI：

  10.1016/0040-4020(96)00573-x
• 作为产物：
  描述：

  1-对甲苯硫基-吡咯啉-2,5-二酮 、 甲基炔丙基醚 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以85%的产率得到(3-methoxyprop-1-ynyl)-p-tolyl sulfide
  参考文献：
  名称：

  Substituted Alkyne Synthesis under Nonbasic Conditions:  Copper Carboxylate-Mediated, Palladium-Catalyzed Thioalkyne−Boronic Acid Cross-Coupling

  摘要：

  [GRAPHICS]A new methodology for the synthesis of substituted alkynes is described. In the presence of copper(I) thiophene 2-carboxylate (CuTC) or copper (I) 3-methylsalicylate (CuMeSal), the palladium-catalyzed cross-coupling of thioalkyne derivatives with boronic acids affords functionalized alkynes in yields ranging from 39 to 91%. This coupling occurs efficiently under mild, nonbasic conditions with a wide variety of thioalkynes and boronic acids, providing a reaction complementary to the Sonogashira protocol.

  DOI：

  10.1021/ol006807d

文献信息

• Asymmetric approaches to cyclopentenones in the Ni(0)-promoted cyclocarbonylation reaction of allyl halides and acetylenes
  作者：Juan Manuel Villar、Antonio Delgado、Amadeu Llebaria、Josep M. Moretó、Elies Molins、Carles Miravitlles

  DOI：10.1016/0040-4020(96)00573-x

  日期：1996.7

  Different approaches to the asymmetric synthesis of cyclopentenones by means of the Ni(CO)4-promoted alkyne-allyl halide cyclization-carbonylation are reported. The use of acetylenic sulfoxides 1 has proved effective for the synthesis of acyclic, fused [5+8], and spiro [5+5], [5+7], and [5+8] cyclopentenones, whereas placement of the aryl sulfoxide on the allylic system failed to afford any cycloadduct

  报道了通过Ni（CO）4促进的炔-烯丙基卤化物环化-羰基化来不对称合成环戊烯酮的不同方法。乙炔亚砜1的使用已证明对合成无环，稠合[5 + 8]和螺[5 + 5]，[5 + 7]和[5 + 8]环戊烯有效，而芳基亚砜的放置烯丙基体系上的环糊精无法提供任何环加合物。通过这种方法已经获得了手性稠合的[5 + 8]，螺[5 + 7]和[5 + 8]环戊烯酮。最后，当在我们的反应体系中使用不同的同手性α-取代的羧酸盐作为配体时，观察到适度的对映选择性。
• One-Pot Stereoselective Synthesis of (<i>Z</i>)-α-Arylthio-α,β-unsaturated Ketones by Hydrostannylation–Stille Tandem Reaction of Acetylenic Sulfides
  作者：Shengyong You、Wenyan Hao、Mingzhong Cai

  DOI：10.1080/00397910903161850

  日期：2010.5.19

  (Z)-α-Arylthio-α,β-unsaturated ketones can be stereoselectively synthesized in one pot under mild conditions, in good yields, by the palladium-catalyzed hydrostannylation of acetylenic sulfides with tributyltin hydride, followed by Stille coupling with acyl chlorides.

  (Z)-α-芳硫基-α,β-不饱和酮可以在温和条件下在一锅中立体选择性地合成，收率良好，通过钯催化乙炔硫化物与三丁基氢化锡的氢化甲硅烷基化，然后用Stille与酰氯偶联。
• Substituted Alkyne Synthesis under Nonbasic Conditions:  Copper Carboxylate-Mediated, Palladium-Catalyzed Thioalkyne−Boronic Acid Cross-Coupling
  作者：Cecile Savarin、Jiri Srogl、Lanny S. Liebeskind

  DOI：10.1021/ol006807d

  日期：2001.1.1

  [GRAPHICS]A new methodology for the synthesis of substituted alkynes is described. In the presence of copper(I) thiophene 2-carboxylate (CuTC) or copper (I) 3-methylsalicylate (CuMeSal), the palladium-catalyzed cross-coupling of thioalkyne derivatives with boronic acids affords functionalized alkynes in yields ranging from 39 to 91%. This coupling occurs efficiently under mild, nonbasic conditions with a wide variety of thioalkynes and boronic acids, providing a reaction complementary to the Sonogashira protocol.
• A SELECTIVE AND CONVENIENT OXIDATION OF ACETYLENIC SULFIDES TO ACETYLENIC SULFOXIDES USING TRICHLOROISOCYANURIC ACID
  作者：Ping Zhong、Meng-Ping Guo、Nan-Ping Huang

  DOI：10.1081/scc-120001999

  日期：2002.1

  Acetylenic sulfides are readily oxidized to acetylenic sulfoxides by a solution of pyridine, water, benzoic acid and trichloroisocyanuric acid in acetonitrile and methylene chloride.