methyl (1S,2S,4R)-N-benzoyl-2-vinyl-7-azabicyclo[2.2.1]heptane-1-carboxylate | 583831-63-4

• 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: methyl (1S,2S,4R)-N-benzoyl-2-vinyl-7-azabicyclo[2.2.1]heptane-1-carboxylate
• 英文别名: (1S,2S,4R)-methyl 7-benzoyl-2-vinyl-7-azabicyclo[2.2.1]heptane-1-carboxylate；methyl (1S,2S,4R)-7-benzoyl-2-ethenyl-7-azabicyclo[2.2.1]heptane-1-carboxylate
• CAS: 583831-63-4
• 化学式: C₁₇H₁₉NO₃
• 分子量: 285.343
• InChiKey: FQNIBIUFOQQSJF-CPUCHLNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (1S,2S,4R)-N-benzoyl-2-vinyl-7-azabicyclo[2.2.1]heptane-1-carboxylate 在 palladium dihydroxide 盐酸 、 氢气 作用下， 以 甲醇 、 水 为溶剂， 反应 48.0h， 生成 (1S,2R,4R)-2-ethyl-7-azabicyclo[2.2.1]heptane-1-carboxylic acid hydrochloride
  参考文献：
  名称：

  Olefination of methyl (1S,2R,4R)-N-benzoyl-2-formyl-7-azabicyclo[2.2.1]heptane-1-carboxylate, a synthetic approach to new conformationally constrained prolines

  摘要：

  Wittig olefinations of methyl (1S,2R,4R)-N-benzoyl-2-formyl-7-azabicyclo[2.2.1]heptane-1-carboxylate with several phosphoranes and the Horner-Wittig reaction, using methyl diethylphosphonoacetate, have been tested in order to evaluate their utility in the synthesis of beta-substituted conformationally constrained prolines. Subsequent elaboration of the resulting alkenes has provided proline-amino acid chimeras [combinations of proline with other alpha-amino acids, such as L-norvaline, L-norleucine, L-alpha-(3-phenylpropyl)glycine or L-homoglutamic acid] with the 7-azabicyclo[2.2.1]heptane skeleton in an enantiomerically pure form. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00200-3
• 作为产物：
  描述：

  methyl (1S,2R,4R)-N-benzoyl-2-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-7-azabicyclo[2.2.1]heptane-1-carboxylate 在 正丁基锂 、 高碘酸 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 为溶剂， 反应 9.42h， 生成 methyl (1S,2S,4R)-N-benzoyl-2-vinyl-7-azabicyclo[2.2.1]heptane-1-carboxylate
  参考文献：
  名称：

  Olefination of methyl (1S,2R,4R)-N-benzoyl-2-formyl-7-azabicyclo[2.2.1]heptane-1-carboxylate, a synthetic approach to new conformationally constrained prolines

  摘要：

  Wittig olefinations of methyl (1S,2R,4R)-N-benzoyl-2-formyl-7-azabicyclo[2.2.1]heptane-1-carboxylate with several phosphoranes and the Horner-Wittig reaction, using methyl diethylphosphonoacetate, have been tested in order to evaluate their utility in the synthesis of beta-substituted conformationally constrained prolines. Subsequent elaboration of the resulting alkenes has provided proline-amino acid chimeras [combinations of proline with other alpha-amino acids, such as L-norvaline, L-norleucine, L-alpha-(3-phenylpropyl)glycine or L-homoglutamic acid] with the 7-azabicyclo[2.2.1]heptane skeleton in an enantiomerically pure form. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00200-3

文献信息

• [EN] ARGINASE INHIBITORS AND METHODS OF USE<br/>[FR] INHIBITEURS D'ARGINASE ET MÉTHODES D'UTILISATION
  申请人：MERCK SHARP & DOHME

  公开号：WO2021141751A1

  公开（公告）日：2021-07-15

  Described herein are compounds of Formula I or a pharmaceutically acceptable salt thereof. The compounds of Formula I act as arginase inhibitors and can be useful in preventing, treating or acting as a remedial agent for arginase-related diseases.

  本文描述了化合物I的结构或其药用盐。化合物I作为精氨酸酶抑制剂，可用于预防、治疗或作为精氨酸酶相关疾病的治疗剂。
• Asymmetric Synthesis of β,β-Disubstituted Alanines via a Sequential C(sp2)–C(sp3) Cross-Coupling–Hydrogenation Strategy
  作者：David A. Petrone、Jonathan Maturano、James Herbort、Erin E. Plasek、J. Mayeli Vivaldo-Nikitovic、David Sarlah

  DOI：10.1021/acs.orglett.4c02376

  日期：2024.7.26

  allows access to a diverse array of valuable β,β-disubstituted alanine derivatives. This synthesis exhibits broad functional group tolerance, and permits efficient access to β-aryl-β-alkyl, and the more rarely reported β,β-dialkyl Ala derivatives with high yield and excellent enantioselectivity. This transformation has been exhibited on decagram quantity, and can be used to generate Fmoc amino acid derivatives

  我们报告了连续 C(SP 2 )–C(SP 3 ) Suzuki 交叉偶联不对称氢化策略的开发，该策略允许获得多种有价值的 β,β-二取代丙氨酸衍生物。该合成表现出广泛的官能团耐受性，并可以有效地获得β-芳基-β-烷基和更罕见报道的β,β-二烷基Ala衍生物，具有高产率和优异的对映选择性。这种转化已在十克数量上得到展示，并且可用于生成可用于 SPPS 的 Fmoc 氨基酸衍生物。