1-tert-butyl 2-methyl 2-[(benzyloxy)methyl]-5-oxo-1H-pyrrole-1,2-(2H,5H)-dicarboxylate | 903528-02-9

• 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: 1-tert-butyl 2-methyl 2-[(benzyloxy)methyl]-5-oxo-1H-pyrrole-1,2-(2H,5H)-dicarboxylate
• 英文别名: 1-O-tert-butyl 2-O-methyl 5-oxo-2-(phenylmethoxymethyl)pyrrole-1,2-dicarboxylate
• CAS: 903528-02-9
• 化学式: C₁₉H₂₃NO₆
• 分子量: 361.395
• InChiKey: JHQPZKZGSWOOAA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  82.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-tert-butyl 2-methyl 2-[(benzyloxy)methyl]-5-oxo-1H-pyrrole-1,2-(2H,5H)-dicarboxylate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 以100%的产率得到(+/-)-methyl 2-benzyloxymethyl-5-oxo-2,5-dihydro-1H-pyrrole-2-carboxylate
  参考文献：
  名称：

  Nitrone [2+3]-Cycloadditions in Stereocontrolled Synthesis of a Potent Proteasome Inhibitor:  (−)-Omuralide

  摘要：

  A new stereocontrolled synthetic route to omuralide has been developed from methyl pyroglutamate. This route involves regio- and stereoselective N-methylnitrone 1,3-dipolar cycloadditions to appropriate pyrrolinones, beta-eliminations, and highly selective hydrogenations as the main steps.

  DOI：

  10.1021/jo701968d
• 作为产物：
  描述：

  5-氧代吡咯烷-2-羧酸乙酯 在 4-二甲氨基吡啶 、 苯基氯化硒 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 生成 1-tert-butyl 2-methyl 2-[(benzyloxy)methyl]-5-oxo-1H-pyrrole-1,2-(2H,5H)-dicarboxylate
  参考文献：
  名称：

  强大的蛋白酶体抑制剂salinosporamide A的合成研究

  摘要：

  已经由焦谷氨酸甲酯通过区域和立体选择性的N-甲基亚硝基环加成合成了α-亚甲基吡咯烷酮，该α-亚甲基吡咯烷酮具有在盐基孢酰胺A及其类似物的合成中高级中间体的所有功能和相对构型。

  DOI：

  10.1016/j.tetlet.2006.04.070

文献信息

• <i>C</i>-(4-Methoxybenzyloxymethyl)-<i>N</i>-methylnitrone Cycloaddition to Highly Functionalized Pyrrolinone: A Regio- and Stereoselective Approach to New Omuralide-Salinosporamide A Hybrids
  作者：Nicole Langlois、Jean-Christophe Legeay、Pascal Retailleau

  DOI：10.1002/ejoc.200800607

  日期：2008.12

  in the synthesis of new omuralide–salinosporamide A hybrids as potential proteasome 20S inhibitors was prepared in a few steps from methyl pyroglutamate. For this purpose, an O-protected hydroxyethyl chain has been successfully introduced to a highly functionalized pyrrolinone by a regio- and stereoselective C-(4-methoxybenzyloxymethyl)-N-methylnitrone 1,3-dipolar cycloaddition. (© Wiley-VCH Verlag

  合成新型 omuralide-salinosporamide A 杂合体作为潜在的蛋白酶体 20S 抑制剂的高级中间体是通过几个步骤从焦谷氨酸甲酯中制备的。为此，通过区域选择性和立体选择性 C-(4-甲氧基苄氧基甲基)-N-甲基硝酮 1,3-偶极环加成反应，已成功将 O-保护的羟乙基链引入高度官能化的吡咯啉酮。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
• Nitrone [2+3]-Cycloadditions in Stereocontrolled Synthesis of a Potent Proteasome Inhibitor:  (−)-Omuralide
  作者：Jean-Christophe Legeay、Nicole Langlois

  DOI：10.1021/jo701968d

  日期：2007.12.1

  A new stereocontrolled synthetic route to omuralide has been developed from methyl pyroglutamate. This route involves regio- and stereoselective N-methylnitrone 1,3-dipolar cycloadditions to appropriate pyrrolinones, beta-eliminations, and highly selective hydrogenations as the main steps.
• Studies toward the synthesis of salinosporamide A, a potent proteasome inhibitor
  作者：Virginie Caubert、Nicole Langlois

  DOI：10.1016/j.tetlet.2006.04.070

  日期：2006.6

  An α-methylenepyrrolidinone bearing all the functionalities and relative configurations of an advanced intermediate in the synthesis of salinosporamide A and analogues has been synthesized from methyl pyroglutamate through regio- and stereoselective N-methylnitrone cycloaddition.

  已经由焦谷氨酸甲酯通过区域和立体选择性的N-甲基亚硝基环加成合成了α-亚甲基吡咯烷酮，该α-亚甲基吡咯烷酮具有在盐基孢酰胺A及其类似物的合成中高级中间体的所有功能和相对构型。