(3S,4R)-1,4-diallyl-3-{(R)-1-[tert-butyl(dimethyl)silyloxy]ethyl}azetidin-2-one | 187145-69-3

• 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,4R)-1,4-diallyl-3-{(R)-1-[tert-butyl(dimethyl)silyloxy]ethyl}azetidin-2-one
• 英文别名: (3S,4R)-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-1,4-bis(prop-2-enyl)azetidin-2-one
• CAS: 187145-69-3
• 化学式: C₁₇H₃₁NO₂Si
• 分子量: 309.524
• InChiKey: CBRHPVSHPLINSW-RBSFLKMASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.99
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3S,4R)-1,4-diallyl-3-{(R)-1-[tert-butyl(dimethyl)silyloxy]ethyl}azetidin-2-one 在 C₆₅H₁₁₁Cl₂N₃O₁₅RuSi₈ 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以91%的产率得到(6R,7S)-7-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-1-azabicyclo[4.2.0]oct-3-en-8-one
  参考文献：
  名称：

  POSS标记的格拉布斯-霍维达型烯烃复分解催化剂的分批和连续纳滤

  摘要：

  合成并表征了带有多面体低聚倍半硅氧烷（POSS）标签的新型分子量增大的复分解催化剂。可以通过使用纳滤技术从反应混合物中回收催化剂，并可以重复使用。发现Starmem 228和PuraMem 280膜成功地将催化剂从反应后混合物中分离至3 ppm以下。还研究了这些带有POSS标签的催化剂在连续复分解反应中的应用。

  DOI：

  10.1002/cssc.201200466
• 作为产物：
  描述：

  4-乙酰氧基氮杂环丁酮 在 氢氧化钾 、 18-冠醚-6 、 三氟甲磺酸三甲基硅酯 、 三乙胺 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 19.0h， 生成 (3S,4R)-1,4-diallyl-3-{(R)-1-[tert-butyl(dimethyl)silyloxy]ethyl}azetidin-2-one
  参考文献：
  名称：

  Highly functionalised monocyclic and bicyclic β-lactams via alkene metathesis

  摘要：

  单环和双环β-内酰胺系统均已制备 通过烯烃复分解反应使用 钼(CH3CPhMe 2 )- （数控 6 H 3 普罗 我 2 )[(OCMe(CF 3 ） 2 ] 2 或者 钌(CHPh)Cl 2 (PCy 3 ） 2 。

  DOI：

  10.1039/a607308e

文献信息

• Batchwise and Continuous Nanofiltration of POSS-Tagged Grubbs-Hoveyda-Type Olefin Metathesis Catalysts
  作者：Anna Kajetanowicz、Justyna Czaban、G. Rajesh Krishnan、Maura Malińska、Krzysztof Woźniak、Humera Siddique、Ludmila G. Peeva、Andrew G. Livingston、Karol Grela

  DOI：10.1002/cssc.201200466

  日期：2013.1

  New molecular‐weight‐enlarged metathesis catalysts, which bear polyhedral oligomeric silsesquioxane (POSS) tags, were synthesized and characterized. The catalysts can be recovered from the reaction mixture by using nanofiltration techniques and can be reused. It was found that the membranes Starmem 228 and PuraMem 280 successfully separate the catalyst from the post‐reaction mixtures to below 3 ppm

  合成并表征了带有多面体低聚倍半硅氧烷（POSS）标签的新型分子量增大的复分解催化剂。可以通过使用纳滤技术从反应混合物中回收催化剂，并可以重复使用。发现Starmem 228和PuraMem 280膜成功地将催化剂从反应后混合物中分离至3 ppm以下。还研究了这些带有POSS标签的催化剂在连续复分解反应中的应用。
• Highly functionalised monocyclic and bicyclic β-lactams via alkene metathesis
  作者：Anthony G. M. Barrett、Simon P. D. Baugh、Vernon C. Gibson、Matthew R. Giles、Edward L. Marshall、Panayiotis A. Procopiou

  DOI：10.1039/a607308e

  日期：——

  Both monocyclic and bicyclic β-lactam systems are prepared via alkene metathesis reactions using Mo(CHCPhMe 2 )- (NC 6 H 3 Pr i 2 )[(OCMe(CF 3 ) 2 ] 2 or Ru(CHPh)Cl 2 (PCy 3 ) 2 .

  单环和双环β-内酰胺系统均已制备 通过烯烃复分解反应使用 钼(CH3CPhMe 2 )- （数控 6 H 3 普罗 我 2 )[(OCMe(CF 3 ） 2 ] 2 或者 钌(CHPh)Cl 2 (PCy 3 ） 2 。
• Rapid Entry into Mono-, Bi-, and Tricyclic β-Lactam Arrays via Alkene Metathesis
  作者：Anthony G. M. Barrett、Simon P. D. Baugh、D. Christopher Braddock、Kevin Flack、Vernon C. Gibson、Matthew R. Giles、Edward L. Marshall、Panayiotis A. Procopiou、Andrew J. P. White、David J. Williams

  DOI：10.1021/jo981150j

  日期：1998.10.1

  4-Acetoxy-2-azetidinone and (3R,4R)-4-acetoxy-3-[(1R)-1-(tert-butyldimethylsilyl)-oxyethyl]-2-azetidinone were converted into 4-alkenyloxy-, 4-(N-allyltoluene-4-sulfonamido)-, 4-(allylthio)-, and 4-alkenyl-2-azetidinone systems. In addition, 4-acetoxy-2-azetidinone and (3R,4R)-4-acetoxy-3-[(1R)-1-(tert-butyldimethylsilyl)-oxyethyl]-2-azetidinone were converted into beta-lactam dienes via sequential C-4 substitution using unsaturated alcohols, allyl mercaptan, N-allyltoluene-4-sulfonamide, and allyl(chloro)dimethylsilane followed by N-allylation. Crossed metathesis of beta-lactam alkenes with styrene partners and ring closing metathesis of beta-lactam dienes using the Schrock [(CF3)(2)MeCO](2)Mo(=CHCMe2Ph)(=NC6H3-2,6-iso-Pr-2) (1) or Grubbs Cl-2(Cy3P)(2)Ru=CHPh (2) carbenes gave diverse monocyclic and bicyclic beta-lactam systems including derivatives of 1-azabicyclo[4.2.0]octan-8-one, 1-azabicyclo[5.2.0]nonan-9-one and its 6-thia, 6-aza, and 6-oxa analogues, 7-oxa-1-azabicyclo[6.2.0]octan-10-one, 8-oxa-1-azabicyclo[7.2.0]octan-11-one, and 9-oxa-1-azabicyclo[8.2.0]octan-12-one. Ring-closing enyne metathesis and tandem ring-closing enyne and diene metathetic reactions were used to produce bicyclic beta-lactam conjugated dienes as exemplified by the conversion of (3S,4R)-(-)-3-[(1R)-(tert-butyldimethylsilyl)oxyethyl]-1-(5-oxa-oct-7-en-2-yn-1-yl)-4-(2-propenyl)-azetidin-2-one (83) into (6R,7S)-(+)-7-[(1R)-(tert-butyldimethylsilyl)oxyethyl]-3-[(2,5-dihydro)-3-furanyl]-1-azabicyclo[4.2.0]oct-3-en-8-one (98).
• Ruthenium nitronate complexes as tunable catalysts for olefin metathesis and other transformations
  作者：Tomasz Wdowik、Cezary Samojłowicz、Magdalena Jawiczuk、Maura Malińska、Krzysztof Woźniak、Karol Grela

  DOI：10.1039/c2cc37385h

  日期：——

  Novel ruthenium(II) complexes were obtained as a result of a stoichiometric reaction of Grubbs’ benzylidene second generation catalysts with 3-nitropropene. These stable complexes, formally ruthenaisoxazole N-oxide derivatives, display activity in both metathesis and non-metathetic processes such as cycloisomerisation, isomerisation and transfer hydrogenation.

  新的铑(II)复合物是通过Grubbs的苯亚甲基第二代催化剂与3-硝基丙烯的化学计量反应获得的。这些稳定的复合物，形式上是铑亚异噁唑N-氧化物衍生物，在交叉烯烃聚合和非交叉过程（如环异构化、异构化和转移氢化）中均表现出活性。
• Hoveyda-Type Quinone-Containing Complexes - Catalysts to Prevent Migration of the Double Bond under Metathesis Conditions
  作者：Anna Kajetanowicz、Mariusz Milewski、Joanna Rogińska、Roman Gajda、Krzysztof Woźniak

  DOI：10.1002/ejoc.201601344

  日期：2017.1.18

  Hoveyda-type complexes have been synthesised and fully characterised. Their ability to suppress undesired double-bond migration along the carbon chain during metathesis reactions was examined. It was proved that these catalysts decrease the amounts of undesired side-products with a shifted double bond in the reaction mixture.

  已经合成并充分表征了三种新的含有醌的 Hoveyda 型配合物。检查了它们在复分解反应期间抑制不希望的双键沿碳链迁移的能力。已证明这些催化剂减少了反应混合物中具有移位双键的不需要的副产物的量。