Naphthalen-1-yl-carbamic acid (3S,6S)-6-hydroxymethyl-2,2,6-trimethyl-tetrahydro-pyran-3-yl ester | 153280-71-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: Naphthalen-1-yl-carbamic acid (3S,6S)-6-hydroxymethyl-2,2,6-trimethyl-tetrahydro-pyran-3-yl ester
• CAS: 153280-71-8
• 化学式: C₂₀H₂₅NO₄
• 分子量: 343.423
• InChiKey: HCRKXMHWLWWXPW-PXNSSMCTSA-N

物化性质

• 沸点：
  466.1±30.0 °C(predicted)
• 密度：
  1.20±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  25.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  67.79
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  Naphthalen-1-yl-carbamic acid (3S,6S)-6-hydroxymethyl-2,2,6-trimethyl-tetrahydro-pyran-3-yl ester 在 pyridine-SO3 complex 作用下， 以 二甲基亚砜 为溶剂， 反应 7.0h， 以80%的产率得到[(3S,6S)-6-formyl-2,2,6-trimethyloxan-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
• 作为产物：
  描述：

  (3R,6S)-6,7-dihydroxy-6,7-dihydrolinalool 在 camphor-10-sulfonic acid sodium tetrahydroborate 、 臭氧 、 对甲苯磺酰氯 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 吡啶 、 二氯甲烷 为溶剂， 反应 27.0h， 生成 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