S(+)-naphthyl carvone | 140185-83-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: S(+)-naphthyl carvone
• 英文别名: (+)-(S)-5-Isopropenyl-2-methyl-3-(1-naphthyl)cyclohex-2-en-1-one；(5S)-2-methyl-3-naphthalen-1-yl-5-prop-1-en-2-ylcyclohex-2-en-1-one
• CAS: 140185-83-7
• 化学式: C₂₀H₂₀O
• 分子量: 276.378
• InChiKey: NWJZUOHVTVLBKC-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.17
• 重原子数：
  21.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  S(+)-naphthyl carvone 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 potassium tert-butylate 、 三正丁基氢锡 、 三溴化硼 作用下， 以 苯 为溶剂， 生成 (+)-(1R,2R,3S,4R,6R,7R)-1,6-Dimethyl-2-(1-naphthyl)-4-phenyltricyclo<4.3.1.03,7>decan-9-one
  参考文献：
  名称：

  区域和立体定向自由基环化途径合成手性三环[4.3.1.o 3,7 ]癸烷（异twistane）系统1（+）-10-α-萘基-5-epi-Pupukean-9-one的合成

  摘要：

  Contrary to that of phenyl derivative 1 the radical 4 adds to radicophiles in an inter- followed by intra-molecular radical Michael addition (radical annulation), furnishing a novel route to chiral isotwistanes 5.

  DOI：

  10.1016/0040-4039(91)80234-w
• 作为产物：
  描述：

  1-溴代萘 、 (R)-Carvone 在 正丁基锂 、 silica gel 、 pyridinium chlorochromate 作用下， 生成 S(+)-naphthyl carvone
  参考文献：
  名称：

  Chiral synthons from carvone. 9. Radical annulation strategy to chiral pupukeanones: total synthesis of (+)-10-exo-(1-naphthyl)pupukean-9-one and (+)-10-exo-(1-naphthyl)-5-epipupukean-9-ones

  摘要：

  Intramolecular alkylation reaction of the bromoenone 12, obtained from S-carvone in three steps, furnished the bicyclo[2.2.2]octenone 13. Contrary to the anticipated radical annulation reaction, the bicyclic bromides 14 and 15, obtained from the enone 13, generated exclusively the cyclopropane product 18 via a 3-exo-trig radical cyclization on reaction with nBu3SnH and AIBN, even in the presence of a large excess of a radicophile. On the other hand, bromoenone 24, synthesized from R-carvone via S-naphthylcarvone 21, underwent radical annulation reaction in the presence of radicophiles to furnish the isotwistanes 25-28 in a regio- and stereospecific manner. Hydrogenation of the olefin 34, obtained from the diketone 27 via a regiospecific Wittig reaction, furnished the naphthyl-5-epipupukean-9-one 33, whereas stereoselective hydrogenation of the enone 36, prepared from the keto ester 25 via a Grignard reaction and dehydration sequence, generated the naphthylpupukeanone 32.

  DOI：

  10.1021/jo00061a026