[(3S)-4-hydroxy-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-3-yl] N-naphthalen-1-ylcarbamate | 153280-70-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: [(3S)-4-hydroxy-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-3-yl] N-naphthalen-1-ylcarbamate
• CAS: 153280-70-7
• 化学式: C₂₀H₂₅NO₄
• 分子量: 343.423
• InChiKey: ATILMNPBMIIEIB-FXAWDEMLSA-N

物化性质

• 沸点：
  472.6±20.0 °C(predicted)
• 密度：
  1.216±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  71.1
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(3S)-4-hydroxy-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-3-yl] N-naphthalen-1-ylcarbamate 在 camphor-10-sulfonic acid 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以68%的产率得到Naphthalen-1-yl-carbamic acid (3S,6S)-6-hydroxymethyl-2,2,6-trimethyl-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  Asymmetric dihydroxylation of linalool, nerolidol and citronellyl acetate. Enantioselective synthesis of (3S, 6S)-tetrahydro-2,2,6-trimethyl-6-vinyl-2H-pyran-3-ol

  摘要：

  The asymmetric Sharpless' dihydroxylation of linalool, citronellyl acetate and nerolidol was investigated. High diastereo-. enantio- and positional selectivity was observed for the first two terpenes. A highly diastereo- and enantioselective synthesis of (3S,6S)-tetrahydro- 2,2,6-trimethyl - 6-vinyl-2H -pyran-3-ol is described.

  DOI：

  10.1016/s0040-4039(00)91832-x
• 作为产物：
  描述：

  Naphthalen-1-yl-carbamic acid (1S,4R)-4,5-dihydroxy-1-(1-hydroxy-1-methyl-ethyl)-4-methyl-pentyl ester 在 对甲苯磺酰氯 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以70%的产率得到[(3S)-4-hydroxy-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-3-yl] N-naphthalen-1-ylcarbamate
  参考文献：
  名称：

  Asymmetric dihydroxylation of linalool, nerolidol and citronellyl acetate. Enantioselective synthesis of (3S, 6S)-tetrahydro-2,2,6-trimethyl-6-vinyl-2H-pyran-3-ol

  摘要：

  The asymmetric Sharpless' dihydroxylation of linalool, citronellyl acetate and nerolidol was investigated. High diastereo-. enantio- and positional selectivity was observed for the first two terpenes. A highly diastereo- and enantioselective synthesis of (3S,6S)-tetrahydro- 2,2,6-trimethyl - 6-vinyl-2H -pyran-3-ol is described.

  DOI：

  10.1016/s0040-4039(00)91832-x