tert-butyl (S)-3-((tert-butyldimethylsilyl)oxy)-2-oxopiperidine-1-carboxylate | 958447-82-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: tert-butyl (S)-3-((tert-butyldimethylsilyl)oxy)-2-oxopiperidine-1-carboxylate
• 英文别名: (s)-1-(t-Butoxycarbonyl)-3-(t-butyldimethyl-silyloxy)piperidin-2-one；tert-butyl (3S)-3-[tert-butyl(dimethyl)silyl]oxy-2-oxopiperidine-1-carboxylate
• CAS: 958447-82-0
• 化学式: C₁₆H₃₁NO₄Si
• 分子量: 329.512
• InChiKey: FYDSQYCFKIDBST-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.93
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl (S)-3-((tert-butyldimethylsilyl)oxy)-2-oxopiperidine-1-carboxylate 在 montmorillonite 、 三乙基硼氢化锂 、 scandium tris(trifluoromethanesulfonate) 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 为溶剂， 反应 0.5h， 生成 (4aR,5S)-5-((tert-butyldimethylsilyl)oxy)-3,3-dimethylhexahydro-1H,3H-pyrido[1,2-c][1,3]oxazin-1-one
  参考文献：
  名称：

  Sc（OTf）3催化的分子内非对映选择性环化从叔丁氧羰基到酰基亚胺离子

  摘要：

  一种访问二元1,3-恶嗪南-2-酮8a - 8c和4,4a，5,6-四氢-[1,3]恶嗪基[3,4-a]喹啉-1（3H）-酮的有效方法8d-8h是通过Sc（OTf）3催化的分子内环化反应从叔丁氧羰基到酰基亚胺离子7a-7j的反应而开发的。各种具有不同环尺寸的取代的N，O-缩醛被证明是该转化的合适底物，并且一系列（4 aS， 6 S， 7 R）-6-OTBS-7-取代的六氢吡咯[1 ，2-c] [1,3] oxazin-1-ones 11a-11j和其他手性二元1,3-oxazinan-2-ones 8i，8j，11k以中等收率合成，具有非对映选择性（dr  > 99：1）。此外，通过这种有趣的路易斯酸催化的分子内环化过程获得了2，5-反式产物11a-11j。

  DOI：

  10.1016/j.tet.2021.131959

文献信息

• Synthesis of Amide Enol Carbamates and Carbonates through Cu(OTf)₂-Catalyzed Reactions of Ynamides with <i>t</i>-Butyl Carbamates/Carbonates
  作者：Pan Han、Zhuo-Ya Mao、Ming Li、Chang-Mei Si、Bang-Guo Wei、Guo-Qiang Lin

  DOI：10.1021/acs.joc.9b03512

  日期：2020.4.3

  A highly regioselective approach to access amide enol carbamates and carbonates 5a–5c′, 7a–7h, and 9 was developed through Cu(OTf)2-catalyzed reactions of ynamides 4 with t-butyl carbamates 2 and 8 and t-butyl carbonates 6. Moreover, this strategy was successfully applied to generate amide enol carbamates 11a–11s and 14a–14f from imides 10 and 13 with ynamides through an N-Boc cleavage–addition ring-opening

  甲高度选择性的方法来访问酰胺烯醇氨基甲酸酯和碳酸酯5A -图5c' ，7A - 7H，和9通过铜（OTF）开发2个的ynamides催化的反应4与吨丁基氨基甲酸酯2和8和吨丁基碳酸盐6。此外，该策略已成功应用于从酰亚胺10和13与乙酰胺通过酰胺生成酰胺烯醇氨基甲酸酯11a - 11s和14a - 14f。N -Boc裂解-加成开环过程。一系列取代基适合该转化，并且以中等至良好的产率获得了所需的酰胺烯醇氨基甲酸酯和碳酸酯。
• SmI₂-mediated intermolecular addition–elimination of piperidine and pyrrolidine <i>N</i>-α-radicals with arylacetylene sulfones
  作者：Chang-Hong Liu、Jia-Ming Guo、Xin Li、Jian-Ting Sun、Bang-Guo Wei、Chang-Mei Si

  DOI：10.1039/d2cc03984b

  日期：——

  An efficient approach to access α-arylacetylene-substituted pyrrolidine and piperidine derivatives has been developed through a samarium diiodide-mediated addition–elimination process of pyrrolidine and piperidine N-α-radicals with arylacetylene sulfones.

  通过二碘化钐介导的吡咯烷和哌啶N -α-自由基与芳基乙炔砜的加成-消除过程，开发了一种获得 α-芳基乙炔取代的吡咯烷和哌啶衍生物的有效方法。
• SmI₂-Mediated Radical Cross-Couplings of α-Hydroxylated Aza-hemiacetals and<i>N</i>,<i>S</i>-Acetals with α,β-Unsaturated Compounds: Asymmetric Synthesis of (+)-Hyacinthacine A₂, (−)-Uniflorine A, and (+)-7-<i>epi</i>-Casuarine
  作者：Xue-Kui Liu、Shi Qiu、Yong-Gang Xiang、Yuan-Ping Ruan、Xiao Zheng、Pei-Qiang Huang

  DOI：10.1021/jo200600n

  日期：2011.6.17

  The SmI2-mediated radical coupling reactions of beta-hydroxylated pyrrolidine/piperidine aza-hemiacetals 8 and 9 and N,S-acetals 6 and 33 with alpha/beta-unsaturated compounds are described. This method allows a rapid access to beta-hydroxylated pyrrolidines, piperidines, pyrrolizidinones, and indolizidinones. Starting from N,S-acetal 33 and via a common intermediate 27, the alkaloids hyacinthacine A(2) (2), uniflorine A (3, 6-epi-casuarine), and the unnatural epimer 7-epi-casuarine (37) have been synthesized in four and five steps with overall yields of 34%, 16%, and 13%, respectively. The radical mechanism of the coupling reactions has been confirmed by controlled experiments, which also allowed deducing the anionic mechanism in the coupling between N,S-acetal 6 and carbonyl compounds. This demonstrates that the mechanisms of these SmI2-mediated reactions are switchable from Barbier-type anionic to radical by cooperative action of BF3 center dot OEt2 and t-BuOH.