acetic acid (R)-7-hydroxy-3,7-dimethyl-6-(naphthalen-1-ylcarbamoyloxy)-oct-2-enyl ester | 270916-01-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: acetic acid (R)-7-hydroxy-3,7-dimethyl-6-(naphthalen-1-ylcarbamoyloxy)-oct-2-enyl ester
• 英文别名: [(E,6R)-7-hydroxy-3,7-dimethyl-6-(naphthalen-1-ylcarbamoyloxy)oct-2-enyl] acetate
• CAS: 270916-01-3
• 化学式: C₂₃H₂₉NO₅
• 分子量: 399.487
• InChiKey: KSBOWJABHHCAHL-DGWAXEAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  acetic acid (R)-7-hydroxy-3,7-dimethyl-6-(naphthalen-1-ylcarbamoyloxy)-oct-2-enyl ester 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 D-(-)-酒石酸二乙酯 、 D(+)-10-樟脑磺酸 、 水 、 potassium carbonate 、 三甲氧基磷 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 50.5h， 生成 Naphthalen-1-yl-carbamic acid (3R,6S)-2,2,6-trimethyl-6-vinyl-tetrahydro-pyran-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
• 作为产物：
  描述：

  乙酸香叶酯 在 吡啶 、 AD-mix-α 、 甲基磺酰胺 作用下， 以 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 50.5h， 生成 acetic acid (R)-7-hydroxy-3,7-dimethyl-6-(naphthalen-1-ylcarbamoyloxy)-oct-2-enyl 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.