2-methyl-1-(thiophen-2-yl)prop-2-en-1-one | 13191-26-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-methyl-1-(thiophen-2-yl)prop-2-en-1-one
• 英文别名: 2-Methyl-1-(2-thienyl)-2-propenone；2-methyl-1-thiophen-2-ylprop-2-en-1-one
• CAS: 13191-26-9
• 化学式: C₈H₈OS
• 分子量: 152.217
• InChiKey: AKTCAPPBLTYJPA-UHFFFAOYSA-N

物化性质

• 沸点：
  118-120 °C(Press: 19 Torr)
• 密度：
  1.100±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  45.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-methyl-1-(thiophen-2-yl)prop-2-en-1-one 在 硫酸 作用下， 生成 4,5-dihydro-5-methyl-6H-cyclopentathiophen-6-one
  参考文献：
  名称：

  A Thiophene Isostere of 2-Methyl-1-indanone

  摘要：

  DOI：

  10.1021/ja01153a506
• 作为产物：
  描述：

  1-(2-噻吩基)-1-丙酮 以 盐酸 、 乙醇 为溶剂， 反应 4.0h， 生成 2-methyl-1-(thiophen-2-yl)prop-2-en-1-one
  参考文献：
  名称：

  Bridged Dithienylethylenes as Precursors of Small Bandgap Electrogenerated Conjugated Polymers

  摘要：

  Bridged dithienylethylenes (DTEs) bearing solubilizing alkyl chains at various positions (2-5) have been synthesized by McMurry dimerization of cyclopenta[b]thiophen-6-ones. In order to introduce alkyl substituents at different positions of the DTE molecule, the precursor ketones have been prepared by different strategies based on a combination of Mannich or Wittig-Horner reaction and Friedel-Craft intramolecular cyclization. The position and the length of the alkyl substituents exert a strong effect on the ability of the precursor to undergo electrochemical polymerization. Thus, whereas substitution at the alpha-position of the ethylene linkage (3) results in a rapid inhibition of electropolymerization, introduction of alkyl chains at the beta-position (4, 5) greatly improves the efficiency of the polymerization process. The analysis of the electrochemical and optical properties of the polymers shows that rigidification of the DTE molecule leads to a significant decrease of the oxidation potential and bandgap. A comparative analysis of DTE and its bridged analogues by means of X-ray diffraction reveals, in agreement with experimental and theoretical results, that the observed reduction of both the HOMO-LUMO gap of the precursor and the bandgap of the corresponding polymers are related to a relaxation of bond length alternation in the DTE moiety.

  DOI：

  10.1021/jo9623447

文献信息

• An iron-catalyzed hydroalkylation reaction of α,β-unsaturated ketones with ethers
  作者：Yun Lan、Pei Fan、Xiao-Wei Liu、Fei-Fan Meng、Tanveer Ahmad、Yun-He Xu、Teck-Peng Loh

  DOI：10.1039/c7cc07235j

  日期：——

  A general strategy for the hydroalkylation of vinyl ketones using ethers catalyzed by an iron catalyst is described. This catalytic method permits direct transformation of easily accessible and abundant precursors into highly substituted, structurally diverse and functionally concentrated products.

  描述了使用铁催化剂催化的醚进行乙烯基酮加氢烷基化的一般策略。这种催化方法可将容易获得且丰富的前体直接转化为高度取代的，结构多样且功能集中的产物。
• Enantioselective Organocatalytic Conjugate Addition of Alkenes to α,β-Enones
  作者：Lingyun Cui、Long Zhang、Sanzhong Luo、Jin-Pei Cheng

  DOI：10.1002/ejoc.201402353

  日期：2014.6

  We report the first example of the enantioselective conjugate addition of alkenes (aromatic enamines) to enones catalyzed by chiral primary amines. The reactions encompass a plethora of α,β-enones including difficult α-substituted vinyl ketones to give vinylation adducts in high yields with good enantioselectivity. The methodology is of synthetic potential in accessing chiral functional materials.

  我们报告了烯烃（芳香族烯胺）与手性伯胺催化的烯酮对映选择性共轭加成的第一个例子。该反应包括大量的 α,β-烯酮，包括难以生成的 α-取代乙烯基酮，以高产率和良好的对映选择性得到乙烯基化加合物。该方法在获得手性功能材料方面具有合成潜力。
• Kinetic Resolution of Aryl Alkenylcarbinols Catalyzed by Fc-PIP
  作者：Bin Hu、Meng Meng、Shanshan Jiang、Weiping Deng

  DOI：10.1002/cjoc.201200410

  日期：2012.6

  An effective kinetic resolution of a variety of aryl alkenylcarbinols catalyzed by nonenzymatic acyl transfer catalyst Fc‐PIP was developed, affording corresponding unreacted alcohols in good to excellent ee value up to 99% and with selectivity factors up to 24.

  开发了有效的动力学拆分非芳基酰基转移催化剂Fc-PIP催化的各种芳基烯基羰基醇的方法，可提供相应的未反应的醇，其ee值高达99％，优良的ee值高达24。
• 一种末端烯烃类化合物的合成方法
  申请人：中国科学院兰州化学物理研究所苏州研究院

  公开号：CN108484399B

  公开（公告）日：2021-05-14

  本发明揭示了一种末端烯烃类化合物的合成方法，所述合成方法是在有机溶剂中，以膦叶立德化合物为原料，以二氧化碳为C1合成子，在还原剂条件下，反应制得末端烯烃类化合物，其中，所述膦叶立德化合物、还原剂的摩尔比为1：(1～6)，二氧化碳的压力为1‑3atm，该合成方法操作方便、条件温和、底物适用范围广、效率高，填补现有技术的缺陷，并且，该合成方法以二氧化碳为合成子，能有效吸收二氧化碳，有效预防温室效应。
• Transition-Metal-Free Reductive Deoxygenative Olefination with CO₂
  作者：Dao-Yong Zhu、Wen-Duo Li、Ce Yang、Jie Chen、Ji-Bao Xia

  DOI：10.1021/acs.orglett.8b01155

  日期：2018.6.1

  A new transition-metal-free reductive deoxygenative olefination of phosphorus ylides with CO2, an abundant and sustainable C1 chemical feedstock, is described. This catalytic CO2 fixation afforded β-unsubstituted acrylates and vinyl ketones in good yields with broad scope and good functional group tolerance under mild reaction conditions. Cost-effective and easily handled polymethylhydrosiloxane was

  描述了一种新的无过渡金属的磷酰磷与CO 2的无过渡金属还原性脱氧烯化反应，CO 2是一种丰富且可持续的C1化学原料。通过该催化CO 2固定，可在温和的反应条件下以良好的收率，宽范围和良好的官能团耐受性获得β-未取代的丙烯酸酯和乙烯基酮。具有成本效益且易于处理的聚甲基氢硅氧烷被用作还原剂。事实证明，双（甲硅烷基）乙缩醛是该CO 2还原功能化的关键中间体。