1-O-tert-butyl 2-O-methyl (2S,4R)-6-oxo-4-phenylpiperidine-1,2-dicarboxylate | 227930-65-6

• 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,4R)-6-oxo-4-phenylpiperidine-1,2-dicarboxylate
• CAS: 227930-65-6
• 化学式: C₁₈H₂₃NO₅
• 分子量: 333.384
• InChiKey: SERAETDHXJQOMD-KGLIPLIRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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,4R)-6-oxo-4-phenylpiperidine-1,2-dicarboxylate 在 四丁基氟化铵 作用下， 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 copper(l) iodide 、 间氯过氧苯甲酸 、 lithium hexamethyldisilazane 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 16.0h， 生成 1-O-tert-butyl 2-O-methyl (2S,4R)-6-oxo-4-phenylpiperidine-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

• Stereocontrolled synthesis of a prototype library of enantiopure 2,4-disubstituted 4-aryl-6-piperidinones and piperidines
  作者：Stephen Hanessian、Willem A.L van Otterlo、Ingemar Nilsson、Udo Bauer

  DOI：10.1016/s0040-4039(02)00184-3

  日期：2002.3

  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.
• 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
  作者：Mireille Muller、Angèle Schoenfelder、Bruno Didier、André Mann、Camille-Georges Wermuth

  DOI：10.1039/a809274e

  日期：——

  The α,β-unsaturated lactam 3 was submitted to 1,4-addition of organocuprate reagents R2CuLiI2 (R = Me, Bu or Ph) to provide the 4-substituted compounds 5a–c, 6a–c as a mixture of diastereomers; these intermediates were then transformed into the corresponding α-amino-γ-substituted adipic acids 7a–c, 8a–c.

  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。