ethyl (1S,6R)-6-[(2-methylpropan-2-yl)oxycarbonylamino]cyclohex-3-ene-1-carboxylate | 1201815-19-1

• 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 (1S,6R)-6-[(2-methylpropan-2-yl)oxycarbonylamino]cyclohex-3-ene-1-carboxylate
• CAS: 1201815-19-1
• 化学式: C₁₄H₂₃NO₄
• 分子量: 269.341
• InChiKey: ALLDERRNKWDELI-WDEREUQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 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 (1S,6R)-6-[(2-methylpropan-2-yl)oxycarbonylamino]cyclohex-3-ene-1-carboxylate 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以43%的产率得到ethyl (1R,2R)-2-tert-butoxycarbonylaminocyclohex-4-enecarboxylate
  参考文献：
  名称：

  Efficient synthesis of 3,4- and 4,5-dihydroxy-2-amino-cyclohexanecarboxylic acid enantiomers

  摘要：

  An efficient method for the synthesis of (1S,2R,4R,5S)- and (1R,2R,4R,5S)-2-amino-4,5-dihydroxycyclohexanecarboxylic acids (-)-6 and (-)-9 and (1R,2R,3S,4R)- and (1S,2R,3S,4R)-2-amino-3,4-dihydroxycyclohexanecarboxylic acids (-)-15 and (-)-18 was developed by using the OsO4-catalyzed oxidation of Boc-protected (1S,2R)-2-aminocyclohex-4-enecarboxylic acid (+)-2 and (1R,2S)-2-aminocyclohex-3-ene-carboxylic acid (+)-11. Good yields were obtained. The stereochemistry of the synthesized compounds was proven by NMR spectroscopy. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.09.001
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 ethyl cis-2-amino-4-cyclohexanecarboxylate hydrochloride 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以89%的产率得到ethyl (1S,6R)-6-[(2-methylpropan-2-yl)oxycarbonylamino]cyclohex-3-ene-1-carboxylate
  参考文献：
  名称：

  Efficient synthesis of 3,4- and 4,5-dihydroxy-2-amino-cyclohexanecarboxylic acid enantiomers

  摘要：

  An efficient method for the synthesis of (1S,2R,4R,5S)- and (1R,2R,4R,5S)-2-amino-4,5-dihydroxycyclohexanecarboxylic acids (-)-6 and (-)-9 and (1R,2R,3S,4R)- and (1S,2R,3S,4R)-2-amino-3,4-dihydroxycyclohexanecarboxylic acids (-)-15 and (-)-18 was developed by using the OsO4-catalyzed oxidation of Boc-protected (1S,2R)-2-aminocyclohex-4-enecarboxylic acid (+)-2 and (1R,2S)-2-aminocyclohex-3-ene-carboxylic acid (+)-11. Good yields were obtained. The stereochemistry of the synthesized compounds was proven by NMR spectroscopy. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.09.001

文献信息

• Efficient synthesis of 3,4- and 4,5-dihydroxy-2-amino-cyclohexanecarboxylic acid enantiomers
  作者：Gabriella Benedek、Márta Palkó、Edit Wéber、Tamás A. Martinek、Enikő Forró、Ferenc Fülöp

  DOI：10.1016/j.tetasy.2009.09.001

  日期：2009.10

  An efficient method for the synthesis of (1S,2R,4R,5S)- and (1R,2R,4R,5S)-2-amino-4,5-dihydroxycyclohexanecarboxylic acids (-)-6 and (-)-9 and (1R,2R,3S,4R)- and (1S,2R,3S,4R)-2-amino-3,4-dihydroxycyclohexanecarboxylic acids (-)-15 and (-)-18 was developed by using the OsO4-catalyzed oxidation of Boc-protected (1S,2R)-2-aminocyclohex-4-enecarboxylic acid (+)-2 and (1R,2S)-2-aminocyclohex-3-ene-carboxylic acid (+)-11. Good yields were obtained. The stereochemistry of the synthesized compounds was proven by NMR spectroscopy. (C) 2009 Elsevier Ltd. All rights reserved.