(3S,4S)-3-Bromo-3-((2R,3S)-3-ethyl-oxiranyl)-4-phenyl-1-((S)-1-phenyl-ethyl)-azetidin-2-one | 917110-32-8

• 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: (3S,4S)-3-Bromo-3-((2R,3S)-3-ethyl-oxiranyl)-4-phenyl-1-((S)-1-phenyl-ethyl)-azetidin-2-one
• 英文别名: (3S,4S)-3-bromo-3-[(2R,3S)-3-ethyloxiran-2-yl]-4-phenyl-1-[(1S)-1-phenylethyl]azetidin-2-one
• CAS: 917110-32-8
• 化学式: C₂₁H₂₂BrNO₂
• 分子量: 400.315
• InChiKey: PQKPJUSEPGXCLL-DBDYPOFSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  32.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3S,4S)-3-Bromo-3-((2R,3S)-3-ethyl-oxiranyl)-4-phenyl-1-((S)-1-phenyl-ethyl)-azetidin-2-one 在 sodium azide 、 二甲基氯化铝 、 sodium hydride 作用下， 以 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 2.0h， 生成 (2R,3R,6S)-2-((R)-1-Azido-propyl)-6-phenyl-5-((S)-1-phenyl-ethyl)-1-oxa-5-aza-spiro[2.3]hexan-4-one
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Azido- and Aziridino-hydroxyl-β-lactams through Stereo- and Regioselective Epoxide Ring Opening

  摘要：

  [GRAPHICS]Two new classes of azido- and aziridino-hydroxyl-beta-lactam containing structures have been prepared by means of a stereo- and regioselective epoxide ring opening. The straightforwardness of the procedure makes this strategy useful for the synthesis of potentially bioactive compounds. Some selected examples showed promising activity in acyl CoA-cholesterol acyltransferase inhibition assays.

  DOI：

  10.1021/jo0615652
• 作为产物：
  描述：

  (1S',3R,4S)-3-bromo-3-but-1-enyl-4-phenyl-1-(1-phenylethyl)azetidin-2-one 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 生成 (3S,4S)-3-Bromo-3-((2R,3S)-3-ethyl-oxiranyl)-4-phenyl-1-((S)-1-phenyl-ethyl)-azetidin-2-one 、 (3S,4S)-3-Bromo-3-((2S,3R)-3-ethyl-oxiranyl)-4-phenyl-1-((S)-1-phenyl-ethyl)-azetidin-2-one
  参考文献：
  名称：

  微波增强的路易斯酸催化环氧化合物合成1,3-二氧戊环和恶唑啉

  摘要：

  本文报道了在化学计量或化学计量存在下使用微波辐射作为有效的能源，将非常规的含β-内酰胺的环氧化物快速且高度区域选择性和立体选择性地转化为相应的环状1，3-二氧戊环和恶唑啉。催化量的路易斯酸，无需其他溶剂。这些环状化合物是二醇和氨基醇的保护形式。

  DOI：

  10.1002/adsc.200600516

文献信息

• A Microwave-Enhanced, Lewis Acid-Catalyzed Synthesis of 1,3-Dioxolanes and Oxazolines from Epoxides
  作者：Fides Benfatti、Giuliana Cardillo、Luca Gentilucci、Alessandra Tolomelli、Magda Monari、Fabio Piccinelli

  DOI：10.1002/adsc.200600516

  日期：2007.5.7

  and highly regio- and stereoselective transformation of non-conventional β-lactam-containing epoxides into the corresponding cyclic 1,3-dioxolanes and oxazolines is herein reported, using microwave irradiation as an efficient source of energy, in the presence of stoichiometric or catalytic amounts of Lewis acids, without an additional solvent. These cyclic compounds are the protected forms of diols

  本文报道了在化学计量或化学计量存在下使用微波辐射作为有效的能源，将非常规的含β-内酰胺的环氧化物快速且高度区域选择性和立体选择性地转化为相应的环状1，3-二氧戊环和恶唑啉。催化量的路易斯酸，无需其他溶剂。这些环状化合物是二醇和氨基醇的保护形式。
• Synthesis and Biological Evaluation of Azido- and Aziridino-hydroxyl-β-lactams through Stereo- and Regioselective Epoxide Ring Opening
  作者：Fides Benfatti、Giuliana Cardillo、Luca Gentilucci、Rossana Perciaccante、Alessandra Tolomelli、Alberico Catapano

  DOI：10.1021/jo0615652

  日期：2006.11.1

  [GRAPHICS]Two new classes of azido- and aziridino-hydroxyl-beta-lactam containing structures have been prepared by means of a stereo- and regioselective epoxide ring opening. The straightforwardness of the procedure makes this strategy useful for the synthesis of potentially bioactive compounds. Some selected examples showed promising activity in acyl CoA-cholesterol acyltransferase inhibition assays.