(S)-(-)-1-methyl-3-phenyl-3-hydroxyazetidin-2-one | 115119-00-1

• 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: (S)-(-)-1-methyl-3-phenyl-3-hydroxyazetidin-2-one
• 英文别名: (3S)-3-hydroxy-1-methyl-3-phenylazetidin-2-one
• CAS: 115119-00-1
• 化学式: C₁₀H₁₁NO₂
• 分子量: 177.203
• InChiKey: HESLKSAURQCLQK-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  benzoyltriethylsilane 在 镍 (R,R)-(chloro-salen)Al(Oi-Pr) derivative 、 甲基溴化镁 、 四丁基氟化铵 、 氢气 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 甲苯 为溶剂， -78.0~45.0 ℃ 、689.47 kPa 条件下， 反应 88.0h， 生成 (S)-(-)-1-methyl-3-phenyl-3-hydroxyazetidin-2-one
  参考文献：
  名称：

  Enantioselective Cyanation/Brook Rearrangement/C-Acylation Reactions of Acylsilanes Catalyzed by Chiral Metal Alkoxides

  摘要：

  New catalytic enantioselective cyanation/1,2-Brook rearrangement/C-acylation reactions of acylsilanes (4) with cyanoformate esters (7) are described. The products of the reaction are fully substituted malonic acid derivatives (8). Catalysts for this transformation were discovered via a directed candidate screen of 96 metal-ligand complexes. Optimization of a (salen)aluminum complex revealed significant remote electronic effects and concentration effects. The scope of the reaction was investigated by using a number of aryl acylsilanes and cyanoformate esters. Chemoselective reduction of the reaction products (8) afforded new enantioenriched alpha-hydroxy-alpha-aryl-beta-amino acid derivatives (32-34) and beta-lactams (35 and 36). This reaction provides a simple method for the construction of new nitrogen-containing enantioenriched chiral building blocks.

  DOI：

  10.1021/jo049164e

文献信息

• Enantioselective Photocyclization of Amides to β-Lactam Derivatives in Inclusion Crystals with an Optically Active Host
  作者：Fumio Toda、Hisakazu Miyamoto、Mitsuhiro Inoue、Shunpei Yasaka、Ivanka Matijasic

  DOI：10.1021/jo991832m

  日期：2000.5.1

  Irradiation of inclusion crystals of 2-(N-acyl-N-alkylamino)cyclohex-2-enones and N,N-dimethylphenylglyoxylamide with chiral host molecules gave the optically active N-alkyl-1-azaspiro[3.5]-nonane-2,5-diones and 3-hydroxy-1-methyl-3-phenylazetidin-2-one, respectively. The crystal structure of the 1:1 inclusion complex of N,N-dimethylphenylglyoxylamide with (-)-trans-1,4-bis[3-(o-chlorophenyl)-3-hy

  用手性主体分子辐照2-（N-酰基-N-烷基氨基）环己-2-烯酮和N，N-二甲基苯基乙醛酰胺的包裹体晶体，得到旋光性的N-烷基-1-氮杂螺[3.5]-壬烷-2， 5-二酮和3-羟基-1-甲基-3-苯基氮杂环丁烷-2-一。N，N-二甲基苯基乙醛酰胺与（-）-反式-1,4-双[3-（邻氯苯基）-3-羟基-3-苯基丙-1-炔基]-的1：1包合物的晶体结构通过X射线衍射分析2,3,5,6-四氯-2,5-环己二烯-1,4-二醇。
• Enantioselective Cyanation/Brook Rearrangement/<i>C</i>-Acylation Reactions of Acylsilanes Catalyzed by Chiral Metal Alkoxides
  作者：David A. Nicewicz、Christopher M. Yates、Jeffrey S. Johnson

  DOI：10.1021/jo049164e

  日期：2004.10.1

  New catalytic enantioselective cyanation/1,2-Brook rearrangement/C-acylation reactions of acylsilanes (4) with cyanoformate esters (7) are described. The products of the reaction are fully substituted malonic acid derivatives (8). Catalysts for this transformation were discovered via a directed candidate screen of 96 metal-ligand complexes. Optimization of a (salen)aluminum complex revealed significant remote electronic effects and concentration effects. The scope of the reaction was investigated by using a number of aryl acylsilanes and cyanoformate esters. Chemoselective reduction of the reaction products (8) afforded new enantioenriched alpha-hydroxy-alpha-aryl-beta-amino acid derivatives (32-34) and beta-lactams (35 and 36). This reaction provides a simple method for the construction of new nitrogen-containing enantioenriched chiral building blocks.
• Toda Fumio, Molecular Crystals and Liquid Crystals (1969-1991), 1988, vol. 161, p. 355 - 362
  作者：Toda Fumio

  DOI：——

  日期：——
• Reactions in the solid state. 4. Enantioselective photochemical reactions in crystalline inclusion compounds
  作者：Menahem Kaftory、Minoru Yagi、Koichi Tanaka、Fumio Toda

  DOI：10.1021/jo00253a037

  日期：1988.9
• KAFTORY, MENAHEM;YAGI, MINORU;TANAKA, KOICHI;TODA, FUMIO, J. ORG. CHEM., 53,(1988) N 18, C. 4391-4393
  作者：KAFTORY, MENAHEM、YAGI, MINORU、TANAKA, KOICHI、TODA, FUMIO

  DOI：——

  日期：——