(1'E)-tert-butyl (4S)-2,2-dimethyl-4-(1'-propenyl)-3-oxazolidinecarboxylate | 133625-89-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (1'E)-tert-butyl (4S)-2,2-dimethyl-4-(1'-propenyl)-3-oxazolidinecarboxylate
• 英文别名: (E)-(S)-N-Boc-2,2-dimethyl-4-(1-propenyl)oxazolidine；tert-butyl (4S)-2,2-dimethyl-4-[(E)-prop-1-enyl]-1,3-oxazolidine-3-carboxylate
• CAS: 133625-89-5
• 化学式: C₁₃H₂₃NO₃
• 分子量: 241.331
• InChiKey: HPCPFFAFEZSLCK-JARNTUPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1'E)-tert-butyl (4S)-2,2-dimethyl-4-(1'-propenyl)-3-oxazolidinecarboxylate 、 甲醇 生成 (Z)-(S)-N-Boc-2-amino-3-pentenol
  参考文献：
  名称：

  BEAULIEU, PIERRE L.;DUCEPPE, JEAN-SIMON;JOHNSON, CAROLYNE, J. ORG. CHEM., 56,(1991) N3, C. 4196-4204

  摘要：

  DOI：
• 作为产物：
  描述：

  (R)-(+)-3-Boc-2,2-二甲基恶唑啉-4-甲醛 以62%的产率得到
  参考文献：
  名称：

  BEAULIEU, PIERRE L.;DUCEPPE, JEAN-SIMON;JOHNSON, CAROLYNE, J. ORG. CHEM., 56,(1991) N3, C. 4196-4204

  摘要：

  DOI：

文献信息

• (2<i>S</i>,1‘<i>S</i>,2‘<i>S</i>,3‘<i>R</i>)-2-(2‘-Carboxy-3‘-methylcyclopropyl) Glycine Is a Potent and Selective Metabotropic Group 2 Receptor Agonist with Anxiolytic Properties
  作者：Iván Collado、Concepción Pedregal、Angel Mazón、Juan Félix Espinosa、Jaime Blanco-Urgoiti、Darryle D. Schoepp、Rebecca A. Wright、Bryan G. Johnson、Ann E. Kingston

  DOI：10.1021/jm0110486

  日期：2002.8.1

  asymmetric synthesis and biological activity of (2S,1'S,2'S,3'R)-2-(2'-carboxy-3'-methylcyclopropyl) glycine 7 and its epimer at the C3' center 6 are described. Compound 7 is a highly potent and selective agonist for group 2 metabotropric glutamate receptors (mGluRs). It is also systemically 4 orders of magnitude more active in the fear-potentiated startle model of anxiety in rats than the rigid constrained

  描述了（2S，1'S，2'S，3'R）-2-（2'-羧基-3'-甲基环丙基）甘氨酸7及其在C3'中心6的差向异构体的不对称合成和生物活性。化合物7是第2组代谢型谷氨酸受体（mGluRs）的高效选择性激动剂。与刚性约束双环系统LY354740相比，它在大鼠恐惧增强惊恐模型中的全身活性还高4个数量级。因此，我们已经表明，构象受限的双环系统的高分子复杂性不是获得高度选择性和有效的第2组mGluRs激动剂的必要条件。
• Synthesis of chiral vinylglycines
  作者：Pierre L. Beaulieu、Jean Simon Duceppe、Carolyne Johnson

  DOI：10.1021/jo00013a023

  日期：1991.6

  (R)- or (S)-benzyl 4-formyl-2,2-dimethyl-3-oxazolidinecarboxylate (7a) and (R)- or (S)-1,1-dimethylethyl 4-formyl-2,2-dimethyl-3-oxazolidinecarboxylate (7b), readily available from serine, react with Wittig reagents to give alkenes 8. Selective deprotection followed by oxidation of the resulting unsaturated amino alcohols 9 provides vinylglycines 5 of defined configuration (> 95% ee) and double-bond geometry. D-Vinylglycines are obtained from L-serine, and conversely, D-serine gives beta,gamma-unsaturated amino acids with the L configuration. The double-bond geometry is controlled by the nature of the phosphorous ylide employed. The scope and limitations of this new methodology for the preparation of chiral vinylglycines is examined.