3-(3-Methoxyphenyl)-1-pyrrol-1-ylprop-2-en-1-one | 1201761-99-0

• 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-(3-Methoxyphenyl)-1-pyrrol-1-ylprop-2-en-1-one
• 英文别名: 3-(3-methoxyphenyl)-1-pyrrol-1-ylprop-2-en-1-one
• CAS: 1201761-99-0
• 化学式: C₁₄H₁₃NO₂
• 分子量: 227.263
• InChiKey: NDRGDMJDIZBQMQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(3-Methoxyphenyl)-1-pyrrol-1-ylprop-2-en-1-one 、 diethylphosphine oxide 在 吡啶 、 Dimethylzinc 、 (S,S)-(+)-2,6-双[2-(羟基二苯甲基)-1-吡咯烷基-甲基]-4-甲基苯酚 作用下， 以 甲苯 为溶剂， 以97%的产率得到(S)-3-(diethylphosphoryl)-3-(3-methoxyphenyl)-1-pyrrol-1-yl-propan-1-one
  参考文献：
  名称：

  Catalytic Asymmetric Hydrophosphinylation of α,β-Unsaturated N-Acylpyrroles: Application of Dialkyl Phosphine Oxides in Enantioselective Synthesis of Chiral Phosphine Oxides or Phosphines

  摘要：

  Dialkyl phosphine oxides were introduced in catalytic asymmetric transformations for the first time. An unprecedented phospha-Michael reaction of dialkyl phosphine oxide with alpha,beta-unsaturated N-acylpyrroles was disclosed. Excellent enantioselectivities (94-99% ee) and chemical yields (up to 99%) were achieved with a broad substrate scope of the N-acylpyrroles. Importantly, pyridine was found to be critical to achieve good results for the present reaction.

  DOI：

  10.1021/ol100504h
• 作为产物：
  描述：

  3-甲氧基苯甲醛 、 1-(1H-pyrrol-1-yl)-2-(triphenylphosphoranylidene)ethanone 以 甲苯 为溶剂， 反应 12.0h， 以83%的产率得到3-(3-Methoxyphenyl)-1-pyrrol-1-ylprop-2-en-1-one
  参考文献：
  名称：

  钯催化的不对称[3 + 2]环加成反应的高取代乙烯基亚环戊烯对映体的选择性构建

  摘要：

  一种新的环加合物：亚甲基三亚甲基甲烷（TMM）与α，β-不饱和N-酰基吡咯的标题反应是构建亚乙烯基亚环戊烷的有效方法。使用这种独特的供体的不对称方案利用衍生自反式1,2-二苯乙烯二胺的双二亚氨基亚磷酸酯配体，以优异的收率和对映选择性形成环加合物。

  DOI：

  10.1002/anie.201300275

文献信息

• Azetidine-derived dinuclear zinc catalyzed asymmetric phospha-Michael addition of dialkyl phosphite to α,β-unsaturated carbonyl compounds
  作者：Shanshan Liu、Na Shao、Feng-Zhen Li、Xiao-Chao Yang、Min-Can Wang

  DOI：10.1039/c7ob02222k

  日期：——

  The asymmetric phospha-Michael addition of dialkyl phosphite to α,β-unsaturated carbonyl compounds by using an azetidine-derived dinuclear zinc catalyst was described. The catalyst was proved to be general and efficient for a broad spectrum of enones and α,β-unsaturated N-acylpyrroles. A series of phosphonate-containing compounds were generated with excellent enantioselectivities (up to 99% ee) and

  描述了通过使用氮杂环丁烷衍生的双核锌催化剂将亚磷酸二烷基酯不对称的亚磷酰基-迈克尔加成到α，β-不饱和羰基化合物上。事实证明该催化剂对广泛的烯酮和α，β-不饱和N-酰基吡咯烷酮是通用且有效的。在温和的条件下，无需使用添加剂，即可生成一系列具有优异对映选择性（最高99％ee）和化学收率（最高99％）的含膦酸酯的化合物。对于23种α，β-不饱和羰基化合物实例，获得的产物具有超过95％的ee。观察到正非线性效应，并提出了可能的机理。
• Highly Enantioselective Conjugate Additions of Phosphites to α,β-Unsaturated<i>N</i>-Acylpyrroles and Imines: A Practical Approach to Enantiomerically Enriched Amino Phosphonates
  作者：Depeng Zhao、Yuan Wang、Lijuan Mao、Rui Wang

  DOI：10.1002/chem.200901901

  日期：2009.10.19

  The first highly enantioselective phosphonylation of α,β‐unsaturated N‐acylpyrroles has been developed. Excellent yields (91–99 %) and enantioselectivities (up to >99 % enantiomeric excess (ee)) were observed for a broad spectrum of both phosphites and N‐acylpyrroles under mild conditions. In particular, when diethyl phosphite was employed to test the scope of the N‐acylpyrroles, almost optically pure

  已经开发出第一个高度对映体选择性的α，β-不饱和N-酰基吡咯烷酰基的膦酰基化反应。在温和的条件下，对于亚磷酸酯和N-酰基吡咯，在宽广的亚磷酸酯和N-酰基吡咯中均观察到优异的收率（91–99％）和对映体选择性（高达> 99％对映体过量（ee））。特别是，当使用亚磷酸二乙酯测试N-酰基吡咯的范围时，对于20个N-酰基吡咯的实例，几乎获得了光学纯的产品（98至> 99％  ee）。此外，可以通过几次简单的吡咯基膦酸酯转化获得光学纯的α-取代的β-或γ-氨基膦酸酯。N的多功能性酰基吡咯部分使磷加合物成为强大的手性结构单元，可合成各种含膦酸酯的化合物。最后，本策略也可用于对映选择性高（93到> 99％ee）的N-嘧啶的不对称氢膦酰化反应 。
• Catalytic Asymmetric Hydrophosphinylation of α,β-Unsaturated <i>N</i>-Acylpyrroles: Application of Dialkyl Phosphine Oxides in Enantioselective Synthesis of Chiral Phosphine Oxides or Phosphines
  作者：Depeng Zhao、Lijuan Mao、Yuan Wang、Dongxu Yang、Quanliang Zhang、Rui Wang

  DOI：10.1021/ol100504h

  日期：2010.4.16

  Dialkyl phosphine oxides were introduced in catalytic asymmetric transformations for the first time. An unprecedented phospha-Michael reaction of dialkyl phosphine oxide with alpha,beta-unsaturated N-acylpyrroles was disclosed. Excellent enantioselectivities (94-99% ee) and chemical yields (up to 99%) were achieved with a broad substrate scope of the N-acylpyrroles. Importantly, pyridine was found to be critical to achieve good results for the present reaction.
• Enantioselective Construction of Highly Substituted Vinylidenecylopentanes by Palladium-Catalyzed Asymmetric [3+2] Cycloaddition Reaction
  作者：Barry M. Trost、Autumn Maruniak

  DOI：10.1002/anie.201300275

  日期：2013.6.10

  A new cycloadduct: The title reaction of methylene‐trimethylenemethane (TMM) with α,β‐unsaturated N‐acyl pyrroles is an efficient method for the construction of vinylidenecyclopentanes. An asymmetric protocol using this unique donor forms cycloadducts in excellent yield and enantioselectivity, making use of a bisdiamidophosphite ligand derived from trans‐1,2‐stilbenediamine.

  一种新的环加合物：亚甲基三亚甲基甲烷（TMM）与α，β-不饱和N-酰基吡咯的标题反应是构建亚乙烯基亚环戊烷的有效方法。使用这种独特的供体的不对称方案利用衍生自反式1,2-二苯乙烯二胺的双二亚氨基亚磷酸酯配体，以优异的收率和对映选择性形成环加合物。