(+/-)-1-(O-benzyl)-4-((2-phenyl)ethyl)-2-azetidinone | 218782-74-2

• 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-(O-benzyl)-4-((2-phenyl)ethyl)-2-azetidinone
• 英文别名: 4-(2-phenylethyl)-1-phenylmethoxyazetidin-2-one
• CAS: 218782-74-2
• 化学式: C₁₈H₁₉NO₂
• 分子量: 281.354
• InChiKey: GUDQNSXUXOVRMJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.35
• 重原子数：
  21.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  29.54
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (+/-)-1-(O-benzyl)-4-((2-phenyl)ethyl)-2-azetidinone 在 palladium on activated charcoal 叠氮基三甲基硅烷 、 氢气 、 N,N-二异丙基乙胺 、 cesium fluoride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 0.5h， 生成 (R,R)-3-azido-1-benzyl-4-((2-phenyl)ethyl)-2-azetidinone
  参考文献：
  名称：

  Enantioselective Synthesis of α-Amino Acids from N-Tosyloxy β-Lactams Derived from β-Keto Esters

  摘要：

  A novel synthetic sequence has been developed to convert simple beta-keto esters into enantiomerically enriched alpha-amino acids. The key features of this sequence include the addition of azide to the C3 position of beta-keto ester derived N-tosyloxy-beta-lactams through a concomitant nucleophilic addition/ N-O bond reduction reaction, a mild CsF-induced N1 benzylation of a-azido monocyclic beta-lactams, the preparation of alpha-keto-beta-lactams through a novel four-step sequence from the corresponding 3-azido-1-benzyl-beta-lactams, and TEMPO-mediated ring expansion of these compounds to the corresponding N-carboxy anhydrides (NCAs). In addition, the synthesis, isolation, and characterization of unusual 3-imino and 3-chloramino-beta-lactams is reported.

  DOI：

  10.1021/jo0162437
• 作为产物：
  描述：

  苄氧基胺盐酸盐 在 四氯化碳 、 三甲基铝 、 三乙胺 、 三苯基膦 作用下， 以 正庚烷 、 二氯甲烷 、 乙腈 为溶剂， 生成 (+/-)-1-(O-benzyl)-4-((2-phenyl)ethyl)-2-azetidinone
  参考文献：
  名称：

  Enantioselective Synthesis of α-Amino Acids from N-Tosyloxy β-Lactams Derived from β-Keto Esters

  摘要：

  A novel synthetic sequence has been developed to convert simple beta-keto esters into enantiomerically enriched alpha-amino acids. The key features of this sequence include the addition of azide to the C3 position of beta-keto ester derived N-tosyloxy-beta-lactams through a concomitant nucleophilic addition/ N-O bond reduction reaction, a mild CsF-induced N1 benzylation of a-azido monocyclic beta-lactams, the preparation of alpha-keto-beta-lactams through a novel four-step sequence from the corresponding 3-azido-1-benzyl-beta-lactams, and TEMPO-mediated ring expansion of these compounds to the corresponding N-carboxy anhydrides (NCAs). In addition, the synthesis, isolation, and characterization of unusual 3-imino and 3-chloramino-beta-lactams is reported.

  DOI：

  10.1021/jo0162437

文献信息

• Total Synthesis and Immunosuppressive Activity of (−)-Pateamine A and Related Compounds:  Implementation of a β-Lactam-Based Macrocyclization
  作者：Daniel Romo、Robert M. Rzasa、Helene A. Shea、Kaapjoo Park、Joseph M. Langenhan、Luo Sun、Alexander Akhiezer、Jun O. Liu

  DOI：10.1021/ja981846u

  日期：1998.12.1

  action of pateamine A. Other studies and findings made in the course of the synthesis and described herein include the following: (1) a Stille coupling can be competitive with π-allyl formation, (2) SmI2 effects a mild N−O cleavage of N-benzyloxy-β-lactams, (3) the synthesis of a pateamine A-dexamethasone hybrid molecule for use in a yeast three-hybrid assay was accomplished, and (4) IC50 values were determined

  从海洋海绵 Mycale sp. 中分离出的强效免疫抑制剂 (-)-pateamine A 的不对称合成。被描述。合成中采用的一个关键策略是基于 β-内酰胺的大环化以形成 19 元双内酯大环内酯。该合成证实了 3R、5S、10S、24S 的相对和绝对立体化学，并为研究 Pateamine A 的作用机制奠定了基础。 在合成过程中进行的其他研究和发现包括以下内容：（ 1) Stille 偶联可以与 π-烯丙基形成竞争，(2) SmI2 影响 N-苄氧基-β-内酰胺的温和 N-O 裂解，(3) 合成 Pateamine A-地塞米松混合分子，用于完成了酵母三杂交试验，
• A Single-Pot, Mild Conversion of β-Lactones to β-Lactams
  作者：Hong Woon Yang、Daniel Romo

  DOI：10.1021/jo990826n

  日期：1999.10.1