ethyl (1R,2S)-2-((tert-butoxycarbonyl)amino)cyclopropanecarboxylate | 1421676-91-6

• 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: ethyl (1R,2S)-2-((tert-butoxycarbonyl)amino)cyclopropanecarboxylate
• 英文别名: Ethyl (1S,2R)-2-((tert-butoxycarbonyl)amino)cyclopropane-1-carboxylate；ethyl (1S,2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]cyclopropane-1-carboxylate
• CAS: 1421676-91-6
• 化学式: C₁₁H₁₉NO₄
• 分子量: 229.276
• InChiKey: WQCFOWMOJLYSPS-JGVFFNPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (1R,2S)-2-((tert-butoxycarbonyl)amino)cyclopropanecarboxylate 在 二异丁基氢化铝 作用下， 以 甲苯 为溶剂， 反应 4.0h， 生成 ((1r,2s)-2-(羟基甲基)环丙基)氨基甲酸叔丁酯
  参考文献：
  名称：

  Conformationally restrained carbamoylcholine homologues. Synthesis, pharmacology at neuronal nicotinic acetylcholine receptors and biostructural considerations

  摘要：

  Exploration of small selective ligands for the nicotinic acetylcholine receptors (nAChRs) based on acetylcholine (ACh) has led to the development of potent agonists with clear preference for the 042 nAChR, the most prevalent nAChR subtype in the central nervous system. In this work we present the continuation of these efforts aimed at increasing this subtype selectivity by introduction of conformational restriction in the carbamoylcholine homologue, 3-(dimethylaminobutyl) dimethylcarbamate (DMABC). Our results highlight the importance of the N-carbamoyl substitution in alpha(4)beta(2)-subtype selectivity. Moreover, we have confirmed the non-linear conformation of DMABC bound to nAChRs suggested by recent crystal structures of the compound in complex with the Lymnaea stagnalis ACh binding protein. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.07.029
• 作为产物：
  描述：

  (1R,2R)-2-(乙氧羰基)环丙烷羧酸 在 copper(l) iodide 、 sodium azide 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 为溶剂， 反应 4.0h， 生成 ethyl (1R,2S)-2-((tert-butoxycarbonyl)amino)cyclopropanecarboxylate
  参考文献：
  名称：

  （Salen）Ru（II）催化剂通过不对称环丙烷化形成反式-环-丙基-β-氨基酸衍生物。

  摘要：

  在关键的不对称诱导步骤中，使用手性（Salen）Ru（II）环丙烷化催化剂，可以通过五个步骤以优异的对映选择性合成反式-环丙基β-氨基酸衍生物。这种简便的合成以高总收率进行，可用于制备许多氨基甲酸酯保护的（已证明Cbz和Boc的）β-氨基酸衍生物。

  DOI：

  10.1021/jo0344079

文献信息

• Highly Enantioselective Synthesis of Cyclopropylamine Derivatives via Ru(II)-Pheox-Catalyzed Direct Asymmetric Cyclopropanation of Vinylcarbamates
  作者：Soda Chanthamath、Dao Thi Nguyen、Kazutaka Shibatomi、Seiji Iwasa

  DOI：10.1021/ol303404c

  日期：2013.2.15

  The Ru(II)-Pheox-catalyzed asymmetric cyclopropanation of vinylcarbamates with diazoesters resulted in the corresponding cyclopropylamine derivatives in high yield and excellent diastereoselectivity (up to 96:4) and enantioselectivity (up to 99% ee).
• Conformationally restrained carbamoylcholine homologues. Synthesis, pharmacology at neuronal nicotinic acetylcholine receptors and biostructural considerations
  作者：Mario de la Fuente Revenga、Thomas Balle、Anders A. Jensen、Bente Frølund

  DOI：10.1016/j.ejmech.2015.07.029

  日期：2015.9

  Exploration of small selective ligands for the nicotinic acetylcholine receptors (nAChRs) based on acetylcholine (ACh) has led to the development of potent agonists with clear preference for the 042 nAChR, the most prevalent nAChR subtype in the central nervous system. In this work we present the continuation of these efforts aimed at increasing this subtype selectivity by introduction of conformational restriction in the carbamoylcholine homologue, 3-(dimethylaminobutyl) dimethylcarbamate (DMABC). Our results highlight the importance of the N-carbamoyl substitution in alpha(4)beta(2)-subtype selectivity. Moreover, we have confirmed the non-linear conformation of DMABC bound to nAChRs suggested by recent crystal structures of the compound in complex with the Lymnaea stagnalis ACh binding protein. (C) 2015 Elsevier Masson SAS. All rights reserved.
• <i>trans</i>-Cyclopropyl β-Amino Acid Derivatives via Asymmetric Cyclopropanation Using a (Salen)Ru(II) Catalyst
  作者：Jason A. Miller、Edward J. Hennessy、Will J. Marshall、Mark A. Scialdone、SonBinh T. Nguyen

  DOI：10.1021/jo0344079

  日期：2003.10.1

  trans-Cyclopropyl beta-amino acid derivatives can be synthesized in five steps with excellent enantioselectivities using a chiral (Salen)Ru(II) cyclopropanation catalyst in the key asymmetry-induction step. This facile synthesis proceeds with high overall yield and can be used to prepare a number of carbamate-protected (Cbz and Boc are demonstrated) beta-amino acid derivatives.

  在关键的不对称诱导步骤中，使用手性（Salen）Ru（II）环丙烷化催化剂，可以通过五个步骤以优异的对映选择性合成反式-环丙基β-氨基酸衍生物。这种简便的合成以高总收率进行，可用于制备许多氨基甲酸酯保护的（已证明Cbz和Boc的）β-氨基酸衍生物。