ethyl (1RS,2RS,3RS,4SR)-2-(tert-butoxycarbonylamino)-3,4-epoxycyclohexanecarboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: ethyl (1RS,2RS,3RS,4SR)-2-(tert-butoxycarbonylamino)-3,4-epoxycyclohexanecarboxylate
• 英文别名: ethyl (1R,2R,3R,6S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-7-oxabicyclo[4.1.0]heptane-3-carboxylate
• 化学式: C₁₄H₂₃NO₅
• 分子量: 285.34
• InChiKey: GUHMKGWCYGUGDN-YTWAJWBKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  77.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl (1RS,2RS,3RS,4SR)-2-(tert-butoxycarbonylamino)-3,4-epoxycyclohexanecarboxylate 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 甲苯 为溶剂， 反应 15.0h， 生成 C₂₁H₃₄N₂O₆
  参考文献：
  名称：

  Selective syntheses of novel highly functionalized β-aminocyclohexanecarboxylic acids

  摘要：

  Highly functionalized beta-aminocyclohexanecarboxylate regio- and stereoisomers were synthetized from racemic unsaturated bicyclic beta-lactams via enzymatic resolution, selective transformation of the C-C double bond by stereoselective epoxidation, and regioselective oxirane ring opening with azide or cyanide as nucleophile. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.12.065
• 作为产物：
  描述：

  7-azabicyclo[4.2.0]oct-4-en-8-one 在 氯化亚砜 、 CAL-B enzyme 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲基叔丁基醚 为溶剂， 反应 14.0h， 生成 ethyl (1RS,2RS,3RS,4SR)-2-(tert-butoxycarbonylamino)-3,4-epoxycyclohexanecarboxylate
  参考文献：
  名称：

  Selective syntheses of novel highly functionalized β-aminocyclohexanecarboxylic acids

  摘要：

  Highly functionalized beta-aminocyclohexanecarboxylate regio- and stereoisomers were synthetized from racemic unsaturated bicyclic beta-lactams via enzymatic resolution, selective transformation of the C-C double bond by stereoselective epoxidation, and regioselective oxirane ring opening with azide or cyanide as nucleophile. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.12.065

文献信息

• Efficient continuous-flow synthesis of novel 1,2,3-triazole-substituted β-aminocyclohexanecarboxylic acid derivatives with gram-scale production
  作者：Sándor B Ötvös、Ádám Georgiádes、István M Mándity、Lóránd Kiss、Ferenc Fülöp

  DOI：10.3762/bjoc.9.172

  日期：——

  simple and efficient continuous-flow procedure is reported. The 1,3-dipolar cycloaddition reactions were performed with copper powder as a readily accessible Cu(I) source. Initially, high reaction rates were achieved under high-pressure/high-temperature conditions. Subsequently, the reaction temperature was lowered to room temperature by the joint use of both basic and acidic additives to improve the safety

  报道了以简单有效的连续流动程序制备新型多取代 1,2,3-三唑改性 β-氨基环己烷羧酸衍生物。1,3-偶极环加成反应是用铜粉作为容易获得的 Cu(I) 源进行的。最初，在高压/高温条件下实现了高反应速率。随后，通过联合使用碱性和酸性添加剂将反应温度降至室温以提高合成的安全性，因为叠氮化物将作为不稳定的反应物处理。还进行了放大实验，从而以安全和直接的方式实现了克级生产。得到的 1,2,
• Selective syntheses of novel highly functionalized β-aminocyclohexanecarboxylic acids
  作者：Loránd Kiss、Enikő Forró、Ferenc Fülöp

  DOI：10.1016/j.tet.2011.12.065

  日期：2012.6

  Highly functionalized beta-aminocyclohexanecarboxylate regio- and stereoisomers were synthetized from racemic unsaturated bicyclic beta-lactams via enzymatic resolution, selective transformation of the C-C double bond by stereoselective epoxidation, and regioselective oxirane ring opening with azide or cyanide as nucleophile. (C) 2011 Elsevier Ltd. All rights reserved.