Ethyl 5-deuterio-1,3-oxazole-4-carboxylate | 1134024-31-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: Ethyl 5-deuterio-1,3-oxazole-4-carboxylate
• CAS: 1134024-31-9
• 化学式: C₆H₇NO₃
• 分子量: 142.119
• InChiKey: UBESIXFCSFYQNK-WFVSFCRTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  52.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-恶唑甲酸乙酯 在 氘代丙酮 、 palladium diacetate 、 caesium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 18.0h， 以70%的产率得到Ethyl 5-deuterio-1,3-oxazole-4-carboxylate
  参考文献：
  名称：

  钯催化的恶唑-4-羧酸乙酯的直接钯催化的烯基化，苄基化和烷基化以及烯基，苄基和烷基卤化物†

  摘要：

  这 恶唑-4-羧酸乙酯 在催化量的四氢呋喃存在下，用烯基-，苄基-，烯丙基-和烷基卤化物直接和区域选择性地进行烯基化，苄基化和烷基化。 醋酸钯 使用布赫瓦尔德（Buchwald）的JohnPhos配体制备碳酸铯

  DOI：

  10.1039/b816374j

文献信息

• Mechanism Selection for Regiocontrol in Base-Assisted, Palladium-Catalysed Direct CH Coupling with Halides: First Approach for Oxazole- and Thiazole-4-Carboxylates
  作者：Laure Théveau、Cécile Verrier、Pierrik Lassalas、Thibaut Martin、Georges Dupas、Olivier Querolle、Luc Van Hijfte、Francis Marsais、Christophe Hoarau

  DOI：10.1002/chem.201101615

  日期：2011.12.16

  Both base‐assisted non‐concerted metallation–deprotonation (nCMD) and concerted metallation–deprotonation (CMD) have been identified as two potent operating mechanisms in palladium‐catalysed direct CH coupling of oxazole and thiazole‐4‐carboxylate esters with halides through base‐ and solvent‐effect experiments. Novel C2‐ and C5‐selective CMD direct arylation procedures in oxazole‐ and thiazole‐4‐carboxylate

  两个基地辅助非一致金属化-去质子化（NCMD）和协同金属化-去质子化（CMD）已被确定为在钯催化的直接C上两个有效的操作机构通过与卤化物恶唑的耦合和噻唑-4-羧酸酯ħ碱和溶剂效应实验。然后通过控制电子和空间因素之间的平衡，设计了恶唑和噻唑-4-羧酸酯系列中新颖的C2和C5选择性CMD直接芳基化方法。值得注意的是，钯催化剂和底物之间的电荷相互作用被确定为控制选择性和减少CMD反应中空间因素的影响的参数。
• Ligand controlled orthogonal base-assisted direct C–H bond arylation in oxa(thia)zole-4-carboxylate series. New insights in nCMD mechanism
  作者：Laure Théveau、Olivier Querolle、Georges Dupas、Christophe Hoarau

  DOI：10.1016/j.tet.2013.01.073

  日期：2013.6

  Alkyl- and arylphosphines have been screened in competitive C2-H/C5-H direct phenylation of oxa(thia)zole-4-carboxylates using Cs2CO3 and Rb2CO3 carbonate bases. nCMD-based C2-H selective direct phenylation was highly kinetically reduced (or enhanced) in favor (or to the detriment) of CMD-based direct C5-H phenylation with bromo- and chlorobenzene, respectively, using highly electron-rich ligands. These results gave novel experimental proof in favor of the electrophilic substitution-type mechanism for nCMD process based upon a prior nitrogen-arylpalladium complex interaction that preludes the deprotonation step. (C) 2013 Elsevier Ltd. All rights reserved.
• Direct palladium-catalyzed alkenylation, benzylation and alkylation of ethyl oxazole-4-carboxylate with alkenyl-, benzyl- and alkyl halides
  作者：Cécile Verrier、Christophe Hoarau、Francis Marsais

  DOI：10.1039/b816374j

  日期：——

  The ethyl oxazole-4-carboxylate was directly and regioselectively alkenylated, benzylated and alkylated with alkenyl-, benzyl-, allyl- and alkyl halides in the presence of catalytic amounts of palladium acetate with caesium carbonate using Buchwald's JohnPhos ligand.

  这 恶唑-4-羧酸乙酯 在催化量的四氢呋喃存在下，用烯基-，苄基-，烯丙基-和烷基卤化物直接和区域选择性地进行烯基化，苄基化和烷基化。 醋酸钯 使用布赫瓦尔德（Buchwald）的JohnPhos配体制备碳酸铯