(E)-(2R,3R)-2-Amino-3-(dimethyl-phenyl-silanyl)-hex-4-enoic acid methyl ester | 497065-79-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (E)-(2R,3R)-2-Amino-3-(dimethyl-phenyl-silanyl)-hex-4-enoic acid methyl ester
• 英文别名: methyl (E,2R,3R)-2-amino-3-[dimethyl(phenyl)silyl]hex-4-enoate
• CAS: 497065-79-9
• 化学式: C₁₅H₂₃NO₂Si
• 分子量: 277.439
• InChiKey: CFWRSJYKVWJZRG-JEELVDDXSA-N

物化性质

• 沸点：
  355.5±42.0 °C(Predicted)
• 密度：
  1.00±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.05
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-(2R,3R)-2-Amino-3-(dimethyl-phenyl-silanyl)-hex-4-enoic acid methyl ester 在 platinum(IV) oxide sodium tetrahydroborate 、 氢气 、 magnesium sulfate 、 三氟乙酸 、 三氟乙酸酐 、 scandium tris(trifluoromethanesulfonate) 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 15.5h， 生成 methyl (2S,5R,6R)-6-(4-bromophenyl)-5-methylpiperidine-2-carboxylate
  参考文献：
  名称：

  Convergent Synthesis of Complex Diketopiperazines Derived from Pipecolic Acid Scaffolds and Parallel Screening against GPCR Targets

  摘要：

  A convergent approach to highly functionalized diketopiperazines (DKPs) using enantioenriched pipecolic acids is described. Scandium triflate-catalyzed [4 + 2] aza-annulation was employed to produce stereochemically well-defined building blocks. A resin "catch and release" strategy was devised to convert annulation products to pipecolic acid monomers. Complex diketopiperazines were efficiently assembled utilizing one-pot cyclodimerization of pipecolic acids. Massively parallel screening of the complex DKPs against a panel of molecular targets identified novel ligands for a number of G-protein-coupled receptors (GPCRs).

  DOI：

  10.1021/jo061758p
• 作为产物：
  描述：

  methyl (2R,3R)-α-azido-β-(dimethylphenylsilyl)-(E)-hex-4-enoate 在 盐酸 作用下， 以 乙醚 为溶剂， 生成 (E)-(2R,3R)-2-Amino-3-(dimethyl-phenyl-silanyl)-hex-4-enoic acid methyl ester
  参考文献：
  名称：

  Diastereoselectivity in the osmium tetraoxide promoted dihydroxylation of chiral (E)-crotylsilane: asymmetric synthesis of silyl-functionalized .gamma.-lactones

  摘要：

  The catalytic osmylation of enantiomerically enriched (E)-crotylsilanes (2S,3R)-1 and (2R,3R)-2 containing a homoallylic, nitrogen-bearing stereocenter proceeds with good to high levels of diastereoselection generating silyl-functionalized trans-4,5 substituted gamma-lactones 3 and 5 as the major diastereomers.

  DOI：

  10.1021/jo00054a002

文献信息

• Highly Enantioenriched Tetrahydropyridines from Chiral Organosilanes:  Application to the Synthesis of Quinolizidine Alkaloid (−)-217A
  作者：Hongbing Huang、Thomas F. Spande、James S. Panek

  DOI：10.1021/ja028937i

  日期：2003.1.1

  The tetrahydropyridine and piperidine subunits are widely found in biologically active molecules and natural products. Alhough considerable synthetic efforts have been made to reach these systems, there are few direct methods available for the preparation of enantionenriched tetrahydropyridines. A Lewis acid-promoted intramolecular imine crotylation is described and results in direct access to enantioenriched

  四氢吡啶和哌啶亚基广泛存在于生物活性分子和天然产物中。尽管为达到这些系统已经进行了大量的合成努力，但很少有直接方法可用于制备富含对映体的四氢吡啶。描述了路易斯酸促进的分子内亚胺巴豆化，并导致直接获得具有高非对映选择性的对映体富集的 2,6-顺-和 2,6-反-3-反-三取代四氢吡啶。在 (-)-quinolizidine 217A 的权宜全合成中证明了该方法的应用示例。这种天然产物的绝对立体化学是通过全合成建立的。
• Stereochemical and Skeletal Diversity Employing Pipecolate Ester Scaffolds
  作者：Yu Chen、John A. Porco,、James S. Panek

  DOI：10.1021/ol070321g

  日期：2007.4.1

  [GRAPHICS]The stereocontrolled synthesis of pyridooxazinones by Mg(OTf)(2)-promoted epoxide ring-opening with use of chiral pipecolates as nucleophiles is described. Pyridooxazinone products derived from azido-epoxides can be further rearranged to seven-membered pyridodiazepinones by azide reduction. The sequence of functional group interconversions generates diversity through topological and stereochemical variation.
• Convergent Synthesis of Complex Diketopiperazines Derived from Pipecolic Acid Scaffolds and Parallel Screening against GPCR Targets
  作者：Sivaraman Dandapani、Ping Lan、Aaron B. Beeler、Scott Beischel、Athier Abbas、Bryan L. Roth、John A. Porco,、James S. Panek

  DOI：10.1021/jo061758p

  日期：2006.11.1

  A convergent approach to highly functionalized diketopiperazines (DKPs) using enantioenriched pipecolic acids is described. Scandium triflate-catalyzed [4 + 2] aza-annulation was employed to produce stereochemically well-defined building blocks. A resin "catch and release" strategy was devised to convert annulation products to pipecolic acid monomers. Complex diketopiperazines were efficiently assembled utilizing one-pot cyclodimerization of pipecolic acids. Massively parallel screening of the complex DKPs against a panel of molecular targets identified novel ligands for a number of G-protein-coupled receptors (GPCRs).
• Diastereoselectivity in the osmium tetraoxide promoted dihydroxylation of chiral (E)-crotylsilane: asymmetric synthesis of silyl-functionalized .gamma.-lactones
  作者：James S. Panek、Jing Zhang

  DOI：10.1021/jo00054a002

  日期：1993.1

  The catalytic osmylation of enantiomerically enriched (E)-crotylsilanes (2S,3R)-1 and (2R,3R)-2 containing a homoallylic, nitrogen-bearing stereocenter proceeds with good to high levels of diastereoselection generating silyl-functionalized trans-4,5 substituted gamma-lactones 3 and 5 as the major diastereomers.