4-(tert-butyldiphenylsilyloxy)-2-oxopiperidine-1-carboxylic acid methyl ester | 476014-78-5

• 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: 4-(tert-butyldiphenylsilyloxy)-2-oxopiperidine-1-carboxylic acid methyl ester
• 英文别名: methyl 4-(tert-butyldiphenylsilyloxy)-2-oxopiperidine-1-carboxylate；Methyl 4-((tert-butyldiphenylsilyl)oxy)-2-oxopiperidine-1-carboxylate；methyl 4-[tert-butyl(diphenyl)silyl]oxy-2-oxopiperidine-1-carboxylate
• CAS: 476014-78-5
• 化学式: C₂₃H₂₉NO₄Si
• 分子量: 411.573
• InChiKey: WGFHSPAJIHUMDL-UHFFFAOYSA-N

物化性质

• 沸点：
  504.9±50.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.32
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 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：

  4-(tert-butyldiphenylsilyloxy)-2-oxopiperidine-1-carboxylic acid methyl ester 在 sodium tetrahydroborate 、 硫酸 、 scandium tris(trifluoromethanesulfonate) 作用下， 以 乙醇 、 乙腈 为溶剂， 生成 4-(tert-butyldiphenylsilyloxy)-2-cyanopiperidine carboxylic acid methyl ester
  参考文献：
  名称：

  A Stereodivergent Approach to Substituted 4-Hydroxypiperidines

  摘要：

  A stereodivergent route toward both diastereomeric forms of functionalized 4-hydroxypiperidines has been successfully developed. This route involves biocatalytic generation of the enantiopure starting materials followed by functionalization via N-acyliminium ion-mediated CC-bond formation.

  DOI：

  10.1021/jo025943o
• 作为产物：
  描述：

  4-羟基-2-哌啶酮 在 咪唑 、 4-二甲氨基吡啶 、 正丁基锂 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.5h， 生成 4-(tert-butyldiphenylsilyloxy)-2-oxopiperidine-1-carboxylic acid methyl ester
  参考文献：
  名称：

  A Stereodivergent Approach to Substituted 4-Hydroxypiperidines

  摘要：

  A stereodivergent route toward both diastereomeric forms of functionalized 4-hydroxypiperidines has been successfully developed. This route involves biocatalytic generation of the enantiopure starting materials followed by functionalization via N-acyliminium ion-mediated CC-bond formation.

  DOI：

  10.1021/jo025943o

文献信息

• Stereoselective Synthesis of (2S,4R)-4-Hydroxypipecolic Acid
  作者：Ernesto G. Occhiato、Dina Scarpi、Antonio Guarna

  DOI：10.1002/ejoc.200700849

  日期：2008.1

  A new synthetic route to enantiopure (2S,4R)-4-hydroxypipecolic acid from commercial ethyl (3S)-4-chloro-3-hydroxybutanoate is reported. The synthesis is based on the Pd-catalyzed methoxycarbonylation of a 4-alkoxy-substituted δ-valerolactam-derived vinyl triflate followed by the stereocontrolled hydrogenation of the enamine double bond. The final product was obtained after exhaustive hydrolysis in

  报道了从商业 (3S)-4-氯-3-羟基丁酸乙酯合成对映体纯 (2S,4R)-4-羟基哌啶酸的新途径。该合成基于 Pd 催化的 4-烷氧基取代的 δ-戊内酰胺衍生的三氟甲磺酸乙烯酯的甲氧基羰基化，然后是烯胺双键的立体控制氢化。经过 10 个步骤以 20% 的产率彻底水解后获得最终产品。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
• A Stereodivergent Approach to Substituted 4-Hydroxypiperidines
  作者：Mandy K. S. Vink、Christien A. Schortinghuis、Jordy Luten、Jan H. van Maarseveen、Hans E. Schoemaker、Henk Hiemstra、Floris P. J. T. Rutjes

  DOI：10.1021/jo025943o

  日期：2002.11.1

  A stereodivergent route toward both diastereomeric forms of functionalized 4-hydroxypiperidines has been successfully developed. This route involves biocatalytic generation of the enantiopure starting materials followed by functionalization via N-acyliminium ion-mediated CC-bond formation.