naphthalen-1-yl-carbamic acid (3R,6R)-6[(S)-1,2-dihydroxy-ethyl]-2,2,6-trimethyl-tetrahydropyran-3-yl ester | 270916-04-6

• 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)-6[(S)-1,2-dihydroxy-ethyl]-2,2,6-trimethyl-tetrahydropyran-3-yl ester
• 英文别名: [(3R,6R)-6-[(1S)-1,2-dihydroxyethyl]-2,2,6-trimethyloxan-3-yl] N-naphthalen-1-ylcarbamate
• CAS: 270916-04-6
• 化学式: C₂₁H₂₇NO₅
• 分子量: 373.449
• InChiKey: BOQXQEKFNSVWIY-WAOWUJCRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  88
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  naphthalen-1-yl-carbamic acid (3R,6R)-6[(S)-1,2-dihydroxy-ethyl]-2,2,6-trimethyl-tetrahydropyran-3-yl ester 在 sodium methylate 、 三甲氧基磷 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 28.5h， 生成 (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 geraniol route

  摘要：

  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.

  DOI：

  10.1016/s0957-4166(00)00014-8
• 作为产物：
  描述：

  naphthalen-1-yl-carbamic acid (R)-2-hydroxy-1-[2-((2S,3S)-3-hydroxymethyl-2-methyl-oxiranyl)ethyl]-2-methyl-propyl ester 在 D(+)-10-樟脑磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以110 mg的产率得到naphthalen-1-yl-carbamic acid (3R,6R)-6[(S)-1,2-dihydroxy-ethyl]-2,2,6-trimethyl-tetrahydropyran-3-yl ester
  参考文献：
  名称：

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

  摘要：

  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.

  DOI：

  10.1016/s0957-4166(00)00014-8

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.