(3S,4S)-4-(1-methylallenyl)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-2-azetidinone | 121463-37-4

• 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)-4-(1-methylallenyl)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-2-azetidinone
• CAS: 121463-37-4
• 化学式: C₁₅H₂₇NO₂Si
• 分子量: 281.47
• InChiKey: NBTNPGPBBIRUSH-JHJVBQTASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.24
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3S,4S)-4-(1-methylallenyl)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-2-azetidinone 在 silver tetrafluoroborate 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 以70%的产率得到(5S,6S)-6-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-methyl-1-azabicyclo[3.2.0]hept-3-en-7-one
  参考文献：
  名称：

  Silver Mediated Cyclizations of 4-Allenyl-and 4-(2-Propynyl)azetidinones. A Stereoselective Synthesis of 3-Substituted Δ1-Carbapenems Via N-C3 Closure.

  摘要：

  DOI：

  10.1016/s0040-4039(00)80467-0
• 作为产物：
  描述：

  but-2-ynyltrimethylsilane 、 4-乙酰氧基氮杂环丁酮 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 以65%的产率得到(3S,4S)-4-(1-methylallenyl)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-2-azetidinone
  参考文献：
  名称：

  Silver Mediated Cyclizations of 4-Allenyl-and 4-(2-Propynyl)azetidinones. A Stereoselective Synthesis of 3-Substituted Δ1-Carbapenems Via N-C3 Closure.

  摘要：

  DOI：

  10.1016/s0040-4039(00)80467-0

文献信息

• The Indium-Mediated Selective Introduction of Allenyl and Propargyl Groups at the C4-Position of 2-Azetidinones and the AuCl3-Catalyzed Cyclization of 4-Allenyl-2-azetidinones
  作者：Phil Ho Lee、Heechul Kim、Kooyeon Lee、Misook Kim、Kwanghyun Noh、Hyunseok Kim、Dong Seomoon

  DOI：10.1002/anie.200462512

  日期：2005.3.11
• Synthesis of 4-allenyl and 4-proparyl-2-azetidinone via Zn-mediated Barbier-type reaction and Pt-catalyzed intramolecular amidation to carbapenem skeletons
  作者：Biao Jiang、Hua Tian

  DOI：10.1016/j.tetlet.2007.09.061

  日期：2007.11

  4-Propargyl-2-azetidinone and 4-allenyl-2-azetidinone derivatives can be facilely obtained from 4-acetoxy-2-azetidinone and propargyl bromides via zinc-mediated Barbier-type reaction. A new method has been developed to construct the carbapenem bicyclic nucleus by cyclization of 4-propargyl-2-azetidinone and 4-allenyl-2-azetidinone derivatives catalyzed by PtCl2. (c) 2007 Elsevier Ltd. All rights reserved.
• Palladium Mediated Formation of Δ1- and Δ2-Carbapenems by Cyclofunctionalization of 4-Allenylazetidinones and 4-(2-Propynyl)azetidinones.
  作者：J. Siva Prasad、Lanny S. Liebeskind

  DOI：10.1016/s0040-4039(00)80468-2

  日期：1988.1
• Synthesis of 3-Selena-1-dethiacephems and Selenazepines via Iodocyclization
  作者：Dinesh R. Garud、Mamoru Koketsu

  DOI：10.1021/ol801010y

  日期：2008.8.7

  A convenient approach to synthesize novel selenium-beta-lactams, 3-selena-1-dethiacephems and selenazepines, was accomplished via the regioselective iodocyclization reaction. The substituent of allenyl moieties dramatically influenced the regiochemical outcome in the iodocyclization of allene-selenourea derivatives.
• First iodocyclization reaction of allene–thioureas: an efficient approach to bicyclic β-lactams
  作者：Dinesh R. Garud、Amol R. Jadhav、Santosh V. Lahore、Nilesh M. Kahar、Rohini R. Joshi、Ramesh A. Joshi、Mamoru Koketsu

  DOI：10.1016/j.tetlet.2014.09.004

  日期：2014.10

  The regioselective iodocyclization reaction of allene-thioureas is described, for the first time, for the synthesis of bicyclic beta-lactams. The substitution at the allenyl part heavily influenced the iodocyclization reaction. The iodocyclization reaction of the unsubstituted allene-thioureas afforded six-membered 3-thia-1-dethiacephems whereas, the substituted allene-thiourea afforded seven-membered thiazepines along with five-membered isopenams. (C) 2014 Elsevier Ltd. All rights reserved.