naphthalen-1-yl carbamic acid (3R,6R)-2,2,60trimethyl-6-vinyl-tetrahydro-pyran-3-yl ester | 252857-46-8

• 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 (3R,6R)-2,2,60trimethyl-6-vinyl-tetrahydro-pyran-3-yl ester
• 英文别名: (3R,6R)-tetrahydro-3-(N-1-naphthyl)carbamoyloxy-6-ethenyl-2,2,6-trimethyl-2H-pyuran
• CAS: 252857-46-8
• 化学式: C₂₁H₂₅NO₃
• 分子量: 339.434
• InChiKey: GXRWDDXRTLUACX-NQIIRXRSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.29
• 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：
  0.38
• 拓扑面积：
  47.56
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  naphthalen-1-yl carbamic acid (3R,6R)-2,2,60trimethyl-6-vinyl-tetrahydro-pyran-3-yl ester 在 甲醇 、 sodium methylate 作用下， 反应 2.0h， 以58%的产率得到(3R,6R)-2,2,6-trimethyl-6-vinyl-tetrahydro-pyran-3-ol
  参考文献：
  名称：

  Enantioselective synthesis of each stereoisomer of the pyranoid linalool oxides: the linalool route

  摘要：

  Each of the four enantiomerically pure tetrahydropyran linalool oxides was prepared by separate enantioselective Sharpless dihydroxylation of (R)- or (S)-linalyl acetate with AD-mix-alpha or AD-mix-beta, followed by a completely stereoselective N-phenylselenophthalimide cyclization of an intermediate allylic alcohol. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00359-6
• 作为产物：
  描述：

  (R)-芳樟醇 在 吡啶 、 甲醇 、 4-二甲氨基吡啶 、 甲基磺酰胺 、 AD-mix-β 、 三苯基氢化锡 、 sodium methylate 、 4-甲基苯磺酸吡啶 、 三氯氧磷 作用下， 以 二氯甲烷 、 甲苯 、 叔丁醇 为溶剂， 反应 164.0h， 生成 naphthalen-1-yl carbamic acid (3R,6R)-2,2,60trimethyl-6-vinyl-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  Enantioselective synthesis of each stereoisomer of the pyranoid linalool oxides: the linalool route

  摘要：

  Each of the four enantiomerically pure tetrahydropyran linalool oxides was prepared by separate enantioselective Sharpless dihydroxylation of (R)- or (S)-linalyl acetate with AD-mix-alpha or AD-mix-beta, followed by a completely stereoselective N-phenylselenophthalimide cyclization of an intermediate allylic alcohol. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00359-6

文献信息

• Enantioselective synthesis of each stereoisomer of the pyranoid linalool oxides: the geraniol route
  作者：Giovanni Vidari、Anna Di Rosa、Francesca Castronovo、Giuseppe Zanoni

  DOI：10.1016/s0957-4166(00)00014-8

  日期：2000.3

  Each of the four enantiomerically pure tetrahydropyran linalool oxides was synthesized by an acid-catalyzed cyclization of an appropriate epoxy-alcohol obtained by consecutive Sharpless dihydroxylation (AD) and epoxidation (AE) reactions of geraniol derivatives. An interesting example of double asymmetric induction was observed during the AE of a bis(homoallylic) N-naphthylcarbammae. (C) 2000 Elsevier Science Ltd. All rights reserved.