2-bromo-N,N-bis((R)-1-phenylethyl)acetamide | 1033190-47-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-bromo-N,N-bis((R)-1-phenylethyl)acetamide
• CAS: 1033190-47-4
• 化学式: C₁₈H₂₀BrNO
• 分子量: 346.267
• InChiKey: WCIRIVGTXQPWGK-HUUCEWRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.73
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  20.31
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  2-bromo-N,N-bis((R)-1-phenylethyl)acetamide 在 copper(l) iodide 、 四(三苯基膦)钯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 cesium fluoride 、 lithium chloride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.58h， 生成
  参考文献：
  名称：

  Asymmetric Induction in 8π Electrocyclizations. Design of a Removable Chiral Auxiliary

  摘要：

  The pseudo C-2 symmetric trans diphenyl oxazoline group acts as an effective chiral auxiliary in the 8 pi, 6 pi tandem electrocyclization of a substituted tetraene 1-carboxylic acid. Assignment of absolute stereochemistry to the [4.2.0] bicyclooctadiene product supports a model in which both s-cis and s-trans conformations favor the transition states with the same helical twist. This assignment prefaces the development of analogs of SNF4435 C and D. These natural products demonstrate activity as androgen receptor antagonists and as multidrug resistance (mdr) reversal agents.

  DOI：

  10.1021/ol202932x
• 作为产物：
  描述：

  (+)-双[(R)-1-苯乙基]胺 、 溴乙酰溴 在 potassium carbonate 作用下， 以 二氯甲烷 、 水 为溶剂， 以87%的产率得到2-bromo-N,N-bis((R)-1-phenylethyl)acetamide
  参考文献：
  名称：

  Asymmetric Induction in 8π Electrocyclizations. Design of a Removable Chiral Auxiliary

  摘要：

  The pseudo C-2 symmetric trans diphenyl oxazoline group acts as an effective chiral auxiliary in the 8 pi, 6 pi tandem electrocyclization of a substituted tetraene 1-carboxylic acid. Assignment of absolute stereochemistry to the [4.2.0] bicyclooctadiene product supports a model in which both s-cis and s-trans conformations favor the transition states with the same helical twist. This assignment prefaces the development of analogs of SNF4435 C and D. These natural products demonstrate activity as androgen receptor antagonists and as multidrug resistance (mdr) reversal agents.

  DOI：

  10.1021/ol202932x

文献信息

• C−H Carbene Insertion of α-Diazo Acetamides by Photolysis in Non-Conventional Media
  作者：Nuno R. Candeias、Pedro M. P. Gois、Luis F. Veiros、Carlos A. M. Afonso

  DOI：10.1021/jo800980c

  日期：2008.8.1

  Light from a mercury vapor high-pressure lamp was used to induce the photolytic decomposition of alpha-diazo acetamides in hexane and in nonconventional media such as water or a film. The corresponding beta- and/or gamma-lactams were obtained in reasonable yields and in some cases with good diastereoselectivities with no need to use a metallic catalyst. Experimental studies on chiral substrates demonstrated the occurrence of insertion with retention of configuration.