1-O-tert-butyl 2-O-methyl (2S)-6-oxo-2,3-dihydropyridine-1,2-dicarboxylate | 227930-59-8

• 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: 1-O-tert-butyl 2-O-methyl (2S)-6-oxo-2,3-dihydropyridine-1,2-dicarboxylate
• CAS: 227930-59-8
• 化学式: C₁₂H₁₇NO₅
• 分子量: 255.271
• InChiKey: NTEYHSWZLCBFLM-QMMMGPOBSA-N

物化性质

• 沸点：
  325.3±52.0 °C(Predicted)
• 密度：
  1.203±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-O-tert-butyl 2-O-methyl (2S)-6-oxo-2,3-dihydropyridine-1,2-dicarboxylate 在 三甲基氯硅烷 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 生成 (-)-(2S,4R)-2-hydroxymethyl-4-phenyl-6-piperidinone
  参考文献：
  名称：

  Stereocontrolled synthesis of a prototype library of enantiopure 2,4-disubstituted 4-aryl-6-piperidinones and piperidines

  摘要：

  Addition of a set of aryl cuprates to N-Boc O-TBDPS 2-hydroxymethyl 3.4-unsaturated 6-piperidinones affords syn-adducts in preference to anti when mixed Grignard-cuprates are used. Aryllithio cuprates give more of the anti-isomer in some cases. A library of 2-hydroxymethyl carbamates (27 compounds) and 2-hydroxymethyl aryl ethers and thioethers (19 compounds) was generated from a selection of 4-aryl-6-piperidinones, and some were further reduced to the corresponding piperidines (9 compounds). (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00184-3
• 作为产物：
  描述：

  methyl (2S)-N-tert-butoxycarbonyl-6-oxopiperidine-2-carboxylate 在 间氯过氧苯甲酸 、 lithium hexamethyldisilazane 作用下， 以 二氯甲烷 为溶剂， 反应 14.0h， 生成 1-O-tert-butyl 2-O-methyl (2S)-6-oxo-2,3-dihydropyridine-1,2-dicarboxylate
  参考文献：
  名称：

  The synthesis of α-amino-γ-substituted adipic acids: stereoelectronic effects during the 1,4-addition of organocuprates to methyl N-tert-butoxy-6-oxo-1,2,3,6-tetrahydropyridine-2-carboxylate

  摘要：

  将δ,δ-不饱和内酰胺 3 与有机琥珀酸试剂 R2CuLiI2（R = Me、Bu 或 Ph）进行 1,4 加成，得到非对映异构体混合物 4-取代化合物 5aâc、6aâc；然后将这些中间体转化为相应的δ-氨基-δ-取代己二酸 7aâc、8aâc。

  DOI：

  10.1039/a809274e

文献信息

• Design and Synthesis of Diversely Substituted Azacyclic Inhibitors of Endothelin Converting Enzyme
  作者：Stephen Hanessian、Cécile Gauchet、Guillaume Charron、Julien Marin、Philippe Nakache

  DOI：10.1021/jo052649y

  日期：2006.3.31

  azacyclic phosphonic acids were synthesized from l-pyroglutamic acid, 6-oxo-l-pipecolic acid, and their enantiomers. The objective was to study the effect of constraining acyclic inhibitors of endothelin converting enzyme on inhibitory activity. Potential pharmacophoric tethers were introduced by stereocontrolled reactions to give highly substituted pyrrolidine- and piperidine-α-phosphonic acids. Weak

  由1-焦谷氨酸，6-氧-1-哌酸及其对映异构体合成了一系列氮杂环膦酸。目的是研究限制内皮素转化酶的无环抑制剂对抑制活性的影响。通过立体控制反应引入潜在的药效学系链，以得到高度取代的吡咯烷-和哌啶-α-膦酸。对于每个具有相同取代基相对取向的系列的非对映异构体，观察到了弱的抑制活性。
• Stereocontrolled synthesis of enantiopure diversely functionalized prototypical piperidinone libraries, and constrained analogs of 4-substituted 2-amino adipic acid
  作者：Stephen Hanessian、Mehran Seid、Ingemar Nilsson

  DOI：10.1016/s0040-4039(02)00183-1

  日期：2002.3

  Enantiopure 2-substituted 4.5-unsaturated piperidinones were subjected to stereocontrolled nitroalkane additions and the corresponding products were further manipulated to produce 4-aminomethyl derivatives. Diverse substitution led to a set of 4-arylsulfonamides and O-carbamates as examples of prototypical piperidinone libraries with two sites of diversity. (C) 2002 Elsevier Science Ltd. All rights reserved.