methyl (E)-6-(2-formylvinyl)naphthalene-2-carboxylate

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: methyl (E)-6-(2-formylvinyl)naphthalene-2-carboxylate
• 英文别名: methyl 6-[(E)-3-oxoprop-1-enyl]naphthalene-2-carboxylate
• 化学式: C₁₅H₁₂O₃
• 分子量: 240.258
• InChiKey: AVCUOZPJJCSTJB-NSCUHMNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (E)-6-(2-formylvinyl)naphthalene-2-carboxylate 、 亚硝基苯 在 potassium tert-butylate 、 1,3-双(2,6-二异丙基苯基)氯化咪唑鎓 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以75%的产率得到methyl 6-(5-oxo-2-phenylisoxazolidin-3-yl)naphthalene-2-carboxylate
  参考文献：
  名称：

  Organocatalytic Synthesis of N-Phenylisoxazolidin-5-ones and a One-Pot Synthesis of β-Amino Acid Esters

  摘要：

  A novel N-heterocyclic carbene (NHC)-catalyzed C-N bond formation by the reaction of alpha,beta-unsaturated aldehydes and nitrosobenzene to N-phenylisoxazolidin-5-ones, followed by an acid-catalyzed esterification and Bamberger-like rearrangement in a mild one-pot protocol leads to N-p-methoxyphenyl (N-PMP) protected beta-amino acid esters.

  DOI：

  10.1021/ol800003n

文献信息

• N-HETEROCYCLIC CARBENE CATALYZED SYNTHESIS OF N-PHENYLISOXAZOLIDIN-5-ONE DERIVATIVE AND SYNTHESIS OF β-AMINO ACID ESTER DERIVATIVE
  申请人：Zhang Yugen

  公开号：US20100099886A1

  公开（公告）日：2010-04-22

  A process for preparing a N-phenylisoxazolidin-5-one derivative is provided. The process for preparing the N-phenylisoxazolidin-5-one derivative comprises reacting an α,β-unsaturated aldehyde with nitrosobenzene in the presence of a N-heterocyclic carbene (NHC) catalyst. A process for preparing an N-alkoxyphenyl protected β-amino acid ester derivative is further provided. The process for preparing the N-alkoxyphenyl protected β-amino acid ester derivative comprises reacting an α,β-unsaturated aldehyde with nitrosobenzene in the presence of a N-heterocyclic carbene (NHC) catalyst to form a N-phenylisoxazolidin-5-one derivative, and then treating the N-phenylisoxazolidin-5-one derivative with an alcohol in the presence of an acid catalyst. A process for preparing an N-alkoxyphenyl protected β-amino acid ester derivative, comprising treating a N-phenylisoxazolidin-5-one derivative with an alcohol in the presence of an acid catalyst, is also provided.

  提供一种制备N-苯基异噁唑烷-5-酮衍生物的方法。制备N-苯基异噁唑烷-5-酮衍生物的方法包括在N-杂环卡宾（NHC）催化剂的存在下，将α，β-不饱和醛与亚硝基苯反应。进一步提供一种制备N-烷氧基苯基保护的β-氨基酸酯衍生物的方法。制备N-烷氧基苯基保护的β-氨基酸酯衍生物的方法包括在N-杂环卡宾（NHC）催化剂的存在下，将α，β-不饱和醛与亚硝基苯反应以形成N-苯基异噁唑烷-5-酮衍生物，然后在酸催化剂的存在下用醇处理N-苯基异噁唑烷-5-酮衍生物。还提供了一种制备N-烷氧基苯基保护的β-氨基酸酯衍生物的方法，包括在酸催化剂的存在下用醇处理N-苯基异噁唑烷-5-酮衍生物。
• [EN] N-HETEROCYCLIC CARBENE CATALYZED SYNTHESIS OF N-PHENYLISOXAZOLIDIN-5-ONE DERIVATIVE AND SYNTHESIS OF ß -AMINO ACID ESTER DERIVATIVE<br/>[FR] SYNTHÈSE DE CARBÈNE N-HÉTÉROCYCLIQUE CATALYSÉ D'UN DÉRIVÉ DE N-PHÉNYLISOXAZOLIDINE-5-ONE ET SYNTHÈSE D'UN DÉRIVÉ D'ESTER DE ß-ACIDE AMINÉ
  申请人：AGENCY SCIENCE TECH & RES

  公开号：WO2008115149A9

  公开（公告）日：2009-10-15
• Organocatalytic Synthesis of <i>N</i>-Phenylisoxazolidin-5-ones and a One-Pot Synthesis of β-Amino Acid Esters
  作者：Jayasree Seayad、Pranab Kumar Patra、Yugen Zhang、Jackie Y. Ying

  DOI：10.1021/ol800003n

  日期：2008.3.1

  A novel N-heterocyclic carbene (NHC)-catalyzed C-N bond formation by the reaction of alpha,beta-unsaturated aldehydes and nitrosobenzene to N-phenylisoxazolidin-5-ones, followed by an acid-catalyzed esterification and Bamberger-like rearrangement in a mild one-pot protocol leads to N-p-methoxyphenyl (N-PMP) protected beta-amino acid esters.