3-(2-chlorophenyl)-1-(1-methyl-1H-imidazol-2-yl)prop-2-en-1-one | 128204-34-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 3-(2-chlorophenyl)-1-(1-methyl-1H-imidazol-2-yl)prop-2-en-1-one
• CAS: 128204-34-2
• 化学式: C₁₃H₁₁ClN₂O
• 分子量: 246.696
• InChiKey: USVGWTCQMBQZHB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.97
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  34.89
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  trimethyl (5-methylfuran-2-yloxy) silane 、 3-(2-chlorophenyl)-1-(1-methyl-1H-imidazol-2-yl)prop-2-en-1-one 在 2,6-双[(3aS,8aR)-3a,8a-二氢-8H-indeno[1,2-d]恶唑啉-2-基]吡啶 、 scandium tris(trifluoromethanesulfonate) 、 六氟异丙醇 作用下， 以 氯仿 为溶剂， 反应 3.5h， 以92%的产率得到(5R)-5-[(1R)-1-(2-chlorophenyl)-3-(1-methylimidazol-2-yl)-3-oxopropyl]-5-methylfuran-2-one
  参考文献：
  名称：

  手性Sc（III）-或Er（III）-pybox配合物催化α，β-不饱和2-酰基咪唑的不对称乙烯基Mukaiyama-Michael反应

  摘要：

  据报道，由吡咯配体的手性Sc（III）或Er（III）配合物催化的甲硅烷氧基呋喃与α，β-不饱和2-酰基咪唑的高度非对映和对映选择性乙烯基Mukaiyama-Michael反应。反应中形成的对映体富集的γ-丁烯化物进一步转化为高度官能化的γ-内酯，这些γ-内酯是广泛的具有生物活性的天然产物中的重要结构框架。

  DOI：

  10.1039/c7cc01763d

文献信息

• An enantioselective sulfa-Michael addition of alkyl thiols to α,β-unsaturated 2-acyl imidazoles catalyzed by a bifunctional squaramide
  作者：Rupesh K. Jha、Subhrajit Rout、Harshit Joshi、Arko Das、Vinod K. Singh

  DOI：10.1016/j.tet.2019.130800

  日期：2020.1

  An enantioselective catalytic sulfa-Michael addition of alkyl thiols to α,β-unsaturated 2-acyl imidazoles using bifunctional organocatalysts is reported. The methodology works efficiently with low catalyst loading (1 mol%) to furnish sulfa-Michael adducts in excellent yields (up to 98%) and high enantioselectivities (up to 92% ee). A transition state model has been proposed to explain the stereochemical

  报道了使用双官能有机催化剂将烷基硫醇的对映选择性催化磺胺-迈克尔加成到α，β-不饱和2-酰基咪唑上。该方法以低催化剂负载量（1 mol％）有效地工作，以极好的收率（高达98％）和高对映选择性（高达92％ee）提供磺胺-迈克尔加成物。已经提出了过渡状态模型来解释反应的立体化学结果。
• Asymmetric α-Functionalization of 2-Alkyl Azaarenes: Synthesis of Tertiary Fluorides Having Vicinal Stereogenic Centers
  作者：Arko Das、Harshit Joshi、Vinod K. Singh

  DOI：10.1021/acs.orglett.1c03626

  日期：2021.12.17

  An enantioselective approach for synthesizing fluorinated azaarenes containing vicinal quaternary–tertiary stereocenters is summarized. The chiral copper(I)–phosphine complex binds with the azaarenes followed by Michael addition to unsaturated acyl imidazoles, resulting in α-functionalized products with an excellent level of enantioselectivities (up to 99%), diastereoselectivities (>20:1), and yields

  总结了一种合成含有邻位季-叔立体中心的氟化氮杂芳烃的对映选择性方法。手性铜 (I)-膦络合物与氮杂芳烃结合，然后迈克尔加成不饱和酰基咪唑，从而产生具有优异水平对映选择性（高达 99%）、非对映选择性（>20:1）和产量（高达 97%）。此外，还证明了酰基咪唑部分的后官能化。
• Chiral-at-Metal Rh(III) Complex-Catalyzed Michael Addition of Pyrazolones with α,β-Unsaturated 2-Acyl Imidazoles
  作者：Shi-Wu Li、Qian Wan、Qiang Kang

  DOI：10.1021/acs.orglett.8b00040

  日期：2018.3.2

  enantioselective conjugate addition of pyrazolones with α,β-unsaturated 2-acyl imidazoles catalyzed by chiral-at-metal rhodium complex is reported. The corresponding adducts were obtained in good yields (85%–96%) with excellent enantioselectivities (up to >99%). This protocol exhibits extraordinary reactivity, because of the fact that a complex with as little as 0.05 mol % Rh(III) can catalyze the title

  报道了吡唑酮与手性金属铑配合物催化的α，β-不饱和2-酰基咪唑的有效对映选择性共轭加成。以良好的对映选择性（高达> 99％）以良好的收率（85％–96％）获得了相应的加合物。由于具有低至0.05 mol％Rh（III）的络合物可以以优良的对映选择性在克级上催化标题反应，因此该方案具有非凡的反应性。
• Cooperative Catalysis in Multicomponent Reactions: Highly Enantioselective Synthesis of γ-Hydroxyketones with a Quaternary Carbon Stereocenter
  作者：Xiao-Yu Guan、Li-Ping Yang、Wenhao Hu

  DOI：10.1002/anie.200904905

  日期：2010.3.15

  Together they make a difference: An aryl diazoacetate, H2O, and an α,β‐unsaturated 2‐acyl imidazole give γ‐hydroxyketones with a quaternary carbon stereocenter with excellent selectivity only if all three catalyst components shown in the scheme are present. The Michael addition step did not occur when a similar reagent mixture was treated with the [Rh2(OAc)4] catalyst alone. OTf=triflate, Ts=p‐tosyl

  它们一起发挥作用：仅当方案中显示的所有三种催化剂成分均存在时，重氮芳基乙酸酯，H 2 O和α，β-不饱和2-酰基咪唑才能使γ-羟基酮与季碳立构中心具有出色的选择性。当类似的试剂混合物仅用[Rh 2（OAc）4 ]催化剂处理时，没有发生迈克尔加成步骤。OTf =三氟甲磺酸，Ts =对甲苯磺酰基。
• Catalytic Asymmetric Michael Reaction of 5<i>H</i>-Oxazol-4-Ones with α,β-Unsaturated Acyl Imidazoles
  作者：Bangzhi Zhang、Fengxia Han、Linqing Wang、Dan Li、Dongxu Yang、Xiaoli Yang、Junxian Yang、Xiaofang Li、Depeng Zhao、Rui Wang

  DOI：10.1002/chem.201503105

  日期：2015.11.23

  asymmetric Michael reaction between 5H‐oxazol‐4‐ones and α,β‐unsaturated acyl imidazoles is reported. A novel 2‐benzo[b]thiophenyl‐modified chiral ProPhenol species is synthesized and used as a ligand, leading to good enantioselectivities in this asymmetric conjugate addition reaction. Furthermore, the introduction of phenol additives as achiral co‐ligands is found to improve the reaction’s chemical yields

  据报道，5 H-恶唑-4-酮与α，β-不饱和酰基咪唑之间存在不对称迈克尔反应。合成了一种新型的2-苯并[ b ]硫代苯基修饰的手性脯酚，并用作配体，从而在该不对称共轭加成反应中产生了良好的对映选择性。此外，发现引入苯酚添加剂作为非手性配体可提高反应的化学收率，非对映选择性和对映选择性。