[(3S,6S)-6-formyl-2,2,6-trimethyloxan-3-yl] N-naphthalen-1-ylcarbamate | 153280-72-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: [(3S,6S)-6-formyl-2,2,6-trimethyloxan-3-yl] N-naphthalen-1-ylcarbamate
• CAS: 153280-72-9
• 化学式: C₂₀H₂₃NO₄
• 分子量: 341.407
• InChiKey: NAWXMRRJTIDWOP-PXNSSMCTSA-N

物化性质

• 沸点：
  456.9±45.0 °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)：
  3.5
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  甲基三苯基溴化膦 、 [(3S,6S)-6-formyl-2,2,6-trimethyloxan-3-yl] N-naphthalen-1-ylcarbamate 在 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 以72%的产率得到
  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 (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

文献信息

• Studies on the total synthesis of the saponaceolides. 1. Enantioselective synthesis of the spiroketal subunit
  作者：Giovanni Vidari、Gianluigi Lanfranchi、Natalina Pazzi、Stefano Serra

  DOI：10.1016/s0040-4039(99)00366-4

  日期：1999.4

  An asymmetric synthesis of the tricyclic spiroketal subunit of the saponaceolides is described in which the absolute stereochemistry at C-2' and C-6' is established through a conformationally and stereoelectronically controlled cyclization of a dihydroxyketone pyran Intermediate. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Asymmetric dihydroxylation of linalool, nerolidol and citronellyl acetate. Enantioselective synthesis of (3S, 6S)-tetrahydro-2,2,6-trimethyl-6-vinyl-2H-pyran-3-ol
  作者：Giovanni Vidari、Andrea Giori、Antonella Dapiaggi、Gianluigi Lanfranchi

  DOI：10.1016/s0040-4039(00)91832-x

  日期：1993.10

  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.