4-N,N-dimethylamino-α-bromopropiophenone | 135124-12-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-N,N-dimethylamino-α-bromopropiophenone
• 英文别名: 2-Bromo-1-(4-dimethylaminophenyl)-propan-1-one；2-bromo-1-[4-(dimethylamino)phenyl]propan-1-one
• CAS: 135124-12-8
• 化学式: C₁₁H₁₄BrNO
• 分子量: 256.142
• InChiKey: BXJMBQFNOIAQIL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-N,N-dimethylamino-α-bromopropiophenone 在 四(三苯基膦)钯 、 copper(II) bis(trifluoromethanesulfonate) 、 caesium carbonate 、 (S,S)-2,6-双(4-异丙基-2-恶唑啉-2-基)吡啶 、 potassium iodide 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 49.33h， 生成
  参考文献：
  名称：

  Copper-Catalyzed 1,2-Addition of α-Carbonyl Iodides to Alkynes

  摘要：

  Abstractβ,γ‐Unsaturated ketones are an important class of organic molecules. Herein, copper catalysis has been developed for the synthesis of β‐γ‐unsaturated ketones through 1,2‐addition of α‐carbonyl iodides to alkynes. The reactions exhibit wide substrate scope and high functional group tolerance. The reaction products are versatile synthetic intermediates to complex small molecules. The method was applied for the formal synthesis of (±)‐trichostatin A, a histone deacetylase inhibitor.

  DOI：

  10.1002/anie.201410279
• 作为产物：
  描述：

  4'-(二甲基氨基)苯丙酮 在 lithium diisopropyl amide 、 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以53%的产率得到4-N,N-dimethylamino-α-bromopropiophenone
  参考文献：
  名称：

  Copper-Catalyzed 1,2-Addition of α-Carbonyl Iodides to Alkynes

  摘要：

  Abstractβ,γ‐Unsaturated ketones are an important class of organic molecules. Herein, copper catalysis has been developed for the synthesis of β‐γ‐unsaturated ketones through 1,2‐addition of α‐carbonyl iodides to alkynes. The reactions exhibit wide substrate scope and high functional group tolerance. The reaction products are versatile synthetic intermediates to complex small molecules. The method was applied for the formal synthesis of (±)‐trichostatin A, a histone deacetylase inhibitor.

  DOI：

  10.1002/anie.201410279

文献信息

• Agents for the detection of substrates with hydrolase activity
  申请人：Boehringer Mannheim GmbH

  公开号：US05292669A1

  公开（公告）日：1994-03-08

  A method of detecting hydrolase activity using as substrates the compounds of the formula ##STR1## wherein each of R.sup.1, R.sup.2 and R.sup.3 is C.sub.1 -C.sub.4 alkyl, or phenyl optionally substituted in the meta- or para- position by C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy or mono- or di-(C.sub.1 -C.sub.6)-alkylamino, or optionally substituted by an O-X group in which X is a glycosyl, phosphate or acyl moiety of a natural substrate of the corresponding glycosidase, phosphatase or esterase.

  一种检测水解酶活性的方法，使用化合物作为底物，该化合物的结构式为##STR1## 其中R.sup.1，R.sup.2和R.sup.3中的每一个均为C.sub.1-C.sub.4烷基或苯基，该苯基在间位或对位上可选地被C.sub.1-C.sub.6烷基、C.sub.1-C.sub.6烷氧基或单-或双-(C.sub.1-C.sub.6)-烷基氨基取代，或者可选地被O-X基取代，其中X是相应的糖苷酶、磷酸酶或酯酶的天然底物的糖基、磷酸酯基或酰基。
• Hydrolase-Substrate
  申请人：BOEHRINGER MANNHEIM GMBH

  公开号：EP0423632B1

  公开（公告）日：1995-08-16
• US5292669A
  申请人：——

  公开号：US5292669A

  公开（公告）日：1994-03-08
• Copper-Catalyzed 1,2-Addition of α-Carbonyl Iodides to Alkynes
  作者：Tao Xu、Xile Hu

  DOI：10.1002/anie.201410279

  日期：2015.1.19

  Abstractβ,γ‐Unsaturated ketones are an important class of organic molecules. Herein, copper catalysis has been developed for the synthesis of β‐γ‐unsaturated ketones through 1,2‐addition of α‐carbonyl iodides to alkynes. The reactions exhibit wide substrate scope and high functional group tolerance. The reaction products are versatile synthetic intermediates to complex small molecules. The method was applied for the formal synthesis of (±)‐trichostatin A, a histone deacetylase inhibitor.