2-(3-methoxyprop-1-yn-1-yl)thiophene | 256371-64-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 2-(3-methoxyprop-1-yn-1-yl)thiophene
• 英文别名: 2-(3-methoxy-prop-1-ynyl)-thiophene；2-(3-methoxyprop-1-ynyl)thiophene
• CAS: 256371-64-9
• 化学式: C₈H₈OS
• 分子量: 152.217
• InChiKey: QSQPHFUYHHBTFB-UHFFFAOYSA-N

物化性质

• 沸点：
  222.1±20.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  37.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(3-methoxyprop-1-yn-1-yl)thiophene 在 palladium on activated charcoal 氢气 作用下， 生成 2-(3-Methoxypropyl)thiophene
  参考文献：
  名称：

  设计和制备2-苯甲酰胺基嘧啶作为IKK抑制剂。

  摘要：

  描述，合成，和生物学评估2-苯甲酰胺基嘧啶作为新型的IKK抑制剂。通过优化先导化合物3，化合物16和24被确定为IKK2的良好抑制剂，IC（50）值分别为40和25 nM。在细胞因子释放的急性模型中，化合物16还显示出显着的体内活性。

  DOI：

  10.1016/j.bmcl.2005.09.035
• 作为产物：
  描述：

  2-碘噻吩 、 甲基炔丙基醚 在 copper(l) iodide 、 四(三苯基膦)钯 、 三乙胺 作用下， 以 苯 为溶剂， 反应 24.0h， 以86%的产率得到2-(3-methoxyprop-1-yn-1-yl)thiophene
  参考文献：
  名称：

  The First Regioselective Hydroformylation of Acetylenic Thiophenes Catalyzed by a Zwitterionic Rhodium Complex and Triphenyl Phosphite

  摘要：

  The hydroformylation of acetylenic thiophenes is readily accomplished by using the zwitterionic rhodium catalyst (eta(6)-C6H5BPh3)-Rh+(1,5-COD) and triphenyl phosphite in the presence of CO and H-2. This catalytic system affords, as the major product, the alpha,beta-unsaturated aldehyde with the aldehyde and thiophene attached to the same olefin carbon atom. Assistance of sulfur from the heterocycle provides excellent regioselectivity and yields when the acetylenic unit is a propargyl ether or ester, phenylacetylene, or an enyne.

  DOI：

  10.1021/jo9912653

文献信息

• Nickel-Catalyzed Highly Chemo-, Regio-, and Stereoselective Three-Component Reaction of Norbornene with Two Alkynes
  作者：Kenichi Ogata、Jun Sugasawa、Yuka Atsuumi、Shin-ichi Fukuzawa

  DOI：10.1021/ol9025556

  日期：2010.1.1

  The first three-component reaction of norbornene with two alkynes leading to 1,5-enyne via C−H bond activation of terminal silylacetylene was achieved using a Ni(cod)2/phosphine catalyst. This reaction is applicable for various internal alkynes and norbornene derivatives with high regio- and stereoselectivities.

  使用Ni（cod）2 /膦催化剂实现了降冰片烯与两个炔烃的第一个三组分反应，通过末端甲硅烷基乙炔的CH键活化反应生成1,5-炔烃。该反应适用于具有高区域和立体选择性的各种内部炔烃和降冰片烯衍生物。
• Iron(II) Chloride Catalyzed Alkylation of Propargyl Ethers: Direct Functionalization of an sp³ C-H Bond Adjacent to Oxygen
  作者：Yuhong Zhang、Yongju Xie、Ming Yu

  DOI：10.1055/s-0030-1260131

  日期：2011.9

  Iron(II) chloride catalyzed direct alkylation of sp³ C-H bond adjacent to oxygen in propargyl ethers has been accomplished by the use of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) as oxidant under mild reaction conditions. The reaction proceeded smoothly with a variety of 1,3-diketones leading to β-dicarbonyl ether in moderate yields. In the absence of 1,3-diketones, ynenones were produced by the use of iron(III) chloride and DDQ.

  在温和反应条件下，使用2,3-二氯-5,6-二氰基-1,4-苯醌（DDQ）作为氧化剂，铁(II)氯化物催化实现了炔丙基醚中与氧相邻的sp³ C-H键的直接烷基化。该反应顺利进行，多种1,3-二酮类化合物以中等收率生成β-二羰基醚。在没有1,3-二酮的情况下，使用铁(III)氯化物和DDQ生成亚胺酮。
• Highly Chemoselective Nickel-Catalyzed Three-Component Cross-Trimerization of Three Distinct Alkynes Leading to 1,3-Dien-5-ynes
  作者：Kenichi Ogata、Jun Sugasawa、Shin-ichi Fukuzawa

  DOI：10.1002/anie.200902099

  日期：2009.8.3

  Cross‐yned: The first highly chemoselective three‐component cross‐trimerization between a triisopropylsilylacetylene, an ether‐functionalized unsymmetrical internal alkyne, and a symmetrical internal alkyne leading to a 1,3‐dien‐5‐yne was achieved using a [Ni(cod)2]/PPh3 catalyst. This reaction is applicable for various internal alkynes with high regio‐ and stereoselectivities.

  交叉式：使用[Ni（ cod）2 ] / PPh 3催化剂。该反应适用于具有高区域和立体选择性的各种内部炔烃。
• Enantioselective Rhodium(I)-Catalyzed [3+2] Annulations of Aromatic Ketimines Induced by Directed CH Activations
  作者：Duc N. Tran、Nicolai Cramer

  DOI：10.1002/anie.201105766

  日期：2011.11.18

  selectivity: Highly substituted indenylamines can be obtained with high enantioselectivity by formal [3+2] additions of aryl ketimines with internal alkynes. These rhodium(I)‐catalyzed processes proceed by selective CH activation of one of the two arene substituents, regioselective carbometalation of the alkyne, and enantioselective addition across the imine.

  三重选择性：可以通过将[3 + 2]芳基酮亚胺与内部炔烃正式加成，以高对映体选择性获得高度取代的茚基胺。这些铑（I）催化的过程是通过两个芳烃取代基之一的选择性CH活化，炔烃的区域选择性碳金属化以及在整个亚胺上的对映选择性加成而进行的。
• Access to Sultams by Rhodium(III)-Catalyzed Directed CH Activation
  作者：Manh V. Pham、Baihua Ye、Nicolai Cramer

  DOI：10.1002/anie.201206191

  日期：2012.10.15

  Director's cut: The pharmaceutically relevant sulfonamide group is shown to be a competent directing group for [Cp*Rh(OAc)2]‐catalyzed CH functionalizations. Reactions of the cyclometalated intermediate with internal alkynes provide access to a wide range of sultam derivatives. The reaction is high yielding and works best under aerobic conditions with catalytic amounts of CuOAc as an oxidation mediator

  导演剪辑：药学相关磺酰胺基团被证明是一个主管定向基团的[Cp *的Rh（OAc）2 ]催化的ç  ħ官能化。环金属化中间体与内部炔烃的反应提供了广泛的苏丹阿马衍生物的途径。该反应收率高，在有氧条件下以催化量的CuOAc作为氧化介质可达到最佳效果。Cp * = C 5 Me 5。