ethyl ((1s,4s)-4-hydroxycyclohexyl)carbamate | 71118-95-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl ((1s,4s)-4-hydroxycyclohexyl)carbamate
• CAS: 71118-95-1
• 化学式: C₉H₁₇NO₃
• 分子量: 187.239
• InChiKey: LYNCTVPCPODSQZ-OCAPTIKFSA-N

物化性质

• 沸点：
  323.1±31.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.04
• 重原子数：
  13.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  58.56
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  Cis-4-Aminocyclohexanol 、 碳酸二乙酯 在 双(二丁基氯基锡(四))氧化物 作用下， 反应 1.0h， 以70%的产率得到ethyl ((1s,4s)-4-hydroxycyclohexyl)carbamate
  参考文献：
  名称：

  Interaction of substrate and catalyst during the formation of oxazolidinones from 2-aminoalcohols and diethyl carbonate using recyclable 1,3-dichlorodistannoxanes

  摘要：

  An efficient synthesis of oxazolidinone (OXZ) using 2-aminoalcohols (2AAs) and diethyl carbonate (DEC) as reagents in the presence of recyclable catalyst 1,3-dichloro-1,1,3,3-tetraalkyldistannoxane, [(RR'SnCl)(2)O](2) (1) is reported. 0.5 mol% (with respect to 2AA) of 1 provides OXZ quantitatively within 1 h at 80 C with turnover frequency (TOF) of 200 h(-1). The observed TOF is much higher than the reported value (4 h-1) of the most convenient and commercially feasible K2CO3 catalyst. Chiral 2AAs produce OXZs with 99% ee. Molar dependency of 1, DEC and 2AA is found to be 1:2:2. Molar conductivities (Omega(-1) cm(2) mol(-1)) in DMSO at 25 degrees C are 6.41 for 1a (R = R' = Bu), 5.25 for 1b (R = Bu, R' = Ph), 2.87 for 1c (R = Ph, R' Bu), and 2.21 for 1d (R = R' = Ph) which reveal the mobility of bridged Cl in 1 during reaction. The study of a broad range of substrates and reaction parameters supports a reaction pathway that begins with initial attack by -OH of the pre-formed 2-ethylcarbamato aminoalcohol (2ECA) of 2AA on Sn-b of 1 displacing the bridged Cl. Change in the reaction rates resulted due to various alkyl and aryl substituents on Sn provides better understanding of the distannoxane catalysis, which has not been attempted before for the said reaction. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcata.2011.01.022