1-(p-anisyl)-3,3-dimethyl-4-(formyl)-2-azetidinone | 124870-70-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: 1-(p-anisyl)-3,3-dimethyl-4-(formyl)-2-azetidinone
• 英文别名: 4-formyl-1-(p-methoxyphenyl)-3,3-dimethylazetidin-2-one；1-(p-anisyl)-4-formyl-3,3-dimethyl-2-azetidinone；1-(4-methoxyphenyl)-3,3-dimethyl-4-oxoazetidine-2-carbaldehyde
• CAS: 124870-70-8
• 化学式: C₁₃H₁₅NO₃
• 分子量: 233.267
• InChiKey: JZFFCNVYCNGADJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(p-anisyl)-3,3-dimethyl-4-(formyl)-2-azetidinone 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 对甲氧基苯异氰酸酯
  参考文献：
  名称：

  Lesniak, S., Polish Journal of Chemistry, 1995, vol. 69, # 11, p. 1490 - 1496

  摘要：

  DOI：
• 作为产物：
  描述：

  1,4-bis(4'-methoxyphenyl)-1,4-diazabuta-1,3-diene 在 盐酸 、 lithium diisopropyl amide 作用下， 以 氯仿 为溶剂， 反应 2.0h， 生成 1-(p-anisyl)-3,3-dimethyl-4-(formyl)-2-azetidinone
  参考文献：
  名称：

  Synthesis of novel functionalized monocyclic 2-azetidinones from N,N'-diaryl-α-diimines and lithium ester enolates

  摘要：

  DOI：

  10.1016/s0040-4020(01)80105-8

文献信息

• Identification and optimisation of 3,3-dimethyl-azetidin-2-ones as potent and selective inhibitors of 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1)
  作者：William McCoull、Martin Augustin、Caroline Blake、Anne Ertan、Elaine Kilgour、Stephan Krapp、Jane E. Moore、Nicholas J. Newcombe、Martin J. Packer、Amanda Rees、John Revill、James S. Scott、Nidhal Selmi、Stefan Gerhardt、Derek J. Ogg、Stefan Steinbacher、Paul R. O. Whittamore

  DOI：10.1039/c3md00234a

  日期：——

  3,3-Di-methyl-azetidin-2-ones were identified as potent and selective 11β-HSD1 inhibitors against the human and mouse forms of the enzyme. Structure guided optimisation of LLE was conducted, utilising a key polar interaction and identifying stereochemical preference for the 4S isomer. Metabolic stability was improved to afford oral exposure, providing tool compounds suitable for pre-clinical evaluation

  3,3-二甲基-氮杂环丁烷-2-酮被鉴定为针对人和小鼠形式酶的有效和选择性11β-HSD1抑制剂。利用关键的极性相互作用并确定4S异构体的立体化学偏好性，对LLE进行结构指导的优化。代谢稳定性得到改善，可以口服，提供了适合临床前评估的工具化合物。
• The unusual Baeyer-Villiger rearrangement of β-lactam aldehydes: Totally stereoselective entry to cis-3-substituted 4-formyloxy-2-azetidinones
  作者：Benito Alcaide、Moustafa F. Aly、Miguel A. Sierra

  DOI：10.1016/0040-4039(95)00492-u

  日期：1995.5

  Baeyer-Villiger oxidation of 4-formyl-β-lactams 1 with m-chloroperbenzoic acid in dichloromethane at room temperature is shown to be a convenient method for the preparation of 4-formyloxy-β-lactams 2. Some reactions of novel compounds 2 are also desrcribed.

  的拜尔-维利格氧化4-甲酰基- β内酰胺1与米中在室温下的二氯甲烷氯过苯甲酸被证明是4-甲酰-β内酰胺的制备的简便方法2。还描述了新型化合物2的一些反应。
• <i>N</i>-Heterocyclic Carbene Catalyzed Ring Expansion of 4-Formyl-β-lactams:  Synthesis of Succinimide Derivatives
  作者：Gong-Qiang Li、Yi Li、Li-Xin Dai、Shu-Li You

  DOI：10.1021/ol0713537

  日期：2007.8.1

  N-Heterocyclic carbene (NHC) has been employed as an efficient catalyst for ring expansion of 4-formyl-beta-lactams, allowing the facile synthesis of succinimide derivatives. This organocatalytic process features readily availability of the catalyst, low catalyst loading, and mild reaction conditions.
• Stereoselective Synthesis of 3-Substituted 4-(Formyloxy)-2-azetidinones by the Unusual Baeyer−Villiger Reaction of β-Lactam Aldehydes. Scope and Synthetic Applications
  作者：Benito Alcaide、Moustafa F. Aly、Miguel A. Sierra

  DOI：10.1021/jo9612685

  日期：1996.1.1

  The Baeyer-Villiger oxidation of 4-formyl-beta-lactams 1 with m-CPBA gave 4-(formyloxy) beta-lactams 2 in a simple, efficient, and totally stereoselective process. This reaction is one of the scarce examples of the preferred migration of a carbon moiety in an aliphatic aldehyde. The influence of the substituents at N1 and C3 of the four-membered ring in the Baeyer-Villiger rearrangement has been studied. Thus, alkyl, alkenyl, aryl, and alkyloxy 3-substituted-1-(p-anisyl)-2-azetidinone 1 form exclusively 4-(formyloxy) beta-lactams 2. Amide or acetoxy substituents at C3 of the four-membered ring produce mixtures of 4-(formyloxy) beta-lactams 2 and 4-carboxy beta-lactams 5. The exclusive formation of carboxy derivatives is observed sometimes for 1-alkyl-substituted-2-azetidinones 1. 4-(Formyloxy) beta-lactams 2 are suitable starting materials to prepare different 4-unsubstituted beta-lactams 9 using beta-hydroxy amides 8 as isolable intermediates. The overall transformation 4-formyl-2-azetidinone to 4-unsubstituted beta-lactam is an easy and convenient stereoselective route to these interesting types of compounds.
• ALCAIDE, BENITO;GOMEZ, ANA;PLUMET, JOAQUIN;RODRIRUEZ-LOPEZ, JULIAN, TETRAHEDRON, 45,(1989) N, C. 2751-2762
  作者：ALCAIDE, BENITO、GOMEZ, ANA、PLUMET, JOAQUIN、RODRIRUEZ-LOPEZ, JULIAN

  DOI：——

  日期：——