1-(4-Bromophenyl)-2-(nitromethyl)pentan-1-one | 1252062-46-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4-Bromophenyl)-2-(nitromethyl)pentan-1-one
• CAS: 1252062-46-6
• 化学式: C₁₂H₁₄BrNO₃
• 分子量: 300.152
• InChiKey: FOLGYEOAOSMOGV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  62.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-nitrocinnamaldehyde 、 1-(4-Bromophenyl)-2-(nitromethyl)pentan-1-one 在 (2S)-2-[二苯基[(三甲基硅酯)氧基]甲基]-吡咯烷 、 溶剂黄146 作用下， 以 甲苯 为溶剂， 反应 148.0h， 以48%的产率得到(3S,4R,5R)-2-(4-bromophenyl)-4-nitro-5-(3-nitrophenyl)-3-propylcyclopentene-1-carbaldehyde
  参考文献：
  名称：

  Sequential Organocatalytic Stetter and Michael-Aldol Condensation Reaction: Asymmetric Synthesis of Fully Substituted Cyclopentenes via a [1 + 2 + 2] Annulation Strategy

  摘要：

  A stereoselective synthesis of fully substituted cyclopentenes has been achieved by a sequential organocatalyzed Stetter and Michael-aldol condensation of aromatic aldehydes, nitroalkenes, and alpha,beta-unsaturated aldehydes via the [1 + 2 + 2] annulation strategy with excellent diastereoselectivities and enantioselectivities (up to >99% ee).

  DOI：

  10.1021/ol101969t
• 作为产物：
  描述：

  (1E)-1-nitropent-1-ene 、 对溴苯甲醛 在 3-苄基羟乙基甲基噻唑氯化锂 、 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.25h， 以55%的产率得到1-(4-Bromophenyl)-2-(nitromethyl)pentan-1-one
  参考文献：
  名称：

  Sequential Organocatalytic Stetter and Michael-Aldol Condensation Reaction: Asymmetric Synthesis of Fully Substituted Cyclopentenes via a [1 + 2 + 2] Annulation Strategy

  摘要：

  A stereoselective synthesis of fully substituted cyclopentenes has been achieved by a sequential organocatalyzed Stetter and Michael-aldol condensation of aromatic aldehydes, nitroalkenes, and alpha,beta-unsaturated aldehydes via the [1 + 2 + 2] annulation strategy with excellent diastereoselectivities and enantioselectivities (up to >99% ee).

  DOI：

  10.1021/ol101969t

文献信息

• Dynamic Kinetic Asymmetric Synthesis of Five Contiguous Stereogenic Centers by Sequential Organocatalytic Stetter and Michael−Aldol Reaction: Enantioselective Synthesis of Fully Substituted Cyclopentanols Bearing a Quaternary Stereocenter
  作者：Bor-Cherng Hong、Nitin S. Dange、Che-Sheng Hsu、Ju-Hsiou Liao、Gene-Hsiang Lee

  DOI：10.1021/ol200006e

  日期：2011.3.18

  A synthesis of fully substituted cyclopentanes bearing a quaternary carbon center and five contiguous stereogenic centers has been achieved by sequential organocatalyzed Stetter and Michael−Aldol reactions of heteroaromatic aldehydes, nitroalkenes, and α,β-unsaturated aldehydes via the [1 + 2 + 2] annulation strategy with dynamic kinetic asymmetric transformation and excellent enantioselectivities

  通过[1 + 2 + 2]通过杂芳族醛，硝基烯烃和α，β-不饱和醛的顺序有机催化的Stetter和Michael-Aldol反应，已经实现了带有一个季碳中心和五个连续的立体中心的全取代环戊烷的合成。具有动态动力学不对称转化和出色的对映选择性（高达ee高达99％）的环空策略。
• Sequential Organocatalytic Stetter and Michael-Aldol Condensation Reaction: Asymmetric Synthesis of Fully Substituted Cyclopentenes via a [1 + 2 + 2] Annulation Strategy
  作者：Bor-Cherng Hong、Nitin S. Dange、Che-Sheng Hsu、Ju-Hsiou Liao

  DOI：10.1021/ol101969t

  日期：2010.11.5

  A stereoselective synthesis of fully substituted cyclopentenes has been achieved by a sequential organocatalyzed Stetter and Michael-aldol condensation of aromatic aldehydes, nitroalkenes, and alpha,beta-unsaturated aldehydes via the [1 + 2 + 2] annulation strategy with excellent diastereoselectivities and enantioselectivities (up to >99% ee).