(4aS,9aR)-4a-methyl-1,2,3,4,4a,9,9a,10-octahydro-10-anthracenone | 134522-52-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: (4aS,9aR)-4a-methyl-1,2,3,4,4a,9,9a,10-octahydro-10-anthracenone
• 英文别名: (4aR,9aS)-9a-methyl-1,2,3,4,4a,10-hexahydroanthracen-9-one
• CAS: 134522-52-4
• 化学式: C₁₅H₁₈O
• 分子量: 214.307
• InChiKey: YFIKOFWVMMLMDQ-DOMZBBRYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (2'S,6S)-1-benzyl-6-methyl-6-<<2'-(methoxymethyl)pyrrolidinyl>carbonyl>-1,4-cyclohexadiene 在 盐酸 、 草酰氯 、 Crabtree catalyst 、 氢气 、 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 17.0h， 生成 (4aS,9aR)-4a-methyl-1,2,3,4,4a,9,9a,10-octahydro-10-anthracenone
  参考文献：
  名称：

  Asymmetric syntheses of 1,6-dialkyl-1,4-cyclohexadiene derivatives

  摘要：

  Ortho-lithiation-alkylation of tertiary benzamide 3 provides a series of 2-substituted chiral benzamides 3a-g (Scheme 1). Birch reduction of 3a-j followed by alkylation of the resulting chiral amide enolate with MeI at -78-degress-C gives 1,6-di-alkyl-1,4-cyclohexadiene derivatives 4a-j with excellent diastereoselectivities (Table I). Applications of this asymmetric synthesis are illustrated by conversions of 4g to enantiomerically pure bicyclic lactone 9 and octalone 11 (Scheme III) and 4j to hexahydro-9-anthracenone 14 (Scheme IV).

  DOI：

  10.1021/ja00013a032

文献信息

• SCHULTZ, ARTHUR G.;GREEN, NEAL J., J. AMER. CHEM. SOC., 113,(1991) N3, C. 4931-4936
  作者：SCHULTZ, ARTHUR G.、GREEN, NEAL J.

  DOI：——

  日期：——
• Asymmetric syntheses of 1,6-dialkyl-1,4-cyclohexadiene derivatives
  作者：Arthur G. Schultz、Neal J. Green

  DOI：10.1021/ja00013a032

  日期：1991.6

  Ortho-lithiation-alkylation of tertiary benzamide 3 provides a series of 2-substituted chiral benzamides 3a-g (Scheme 1). Birch reduction of 3a-j followed by alkylation of the resulting chiral amide enolate with MeI at -78-degress-C gives 1,6-di-alkyl-1,4-cyclohexadiene derivatives 4a-j with excellent diastereoselectivities (Table I). Applications of this asymmetric synthesis are illustrated by conversions of 4g to enantiomerically pure bicyclic lactone 9 and octalone 11 (Scheme III) and 4j to hexahydro-9-anthracenone 14 (Scheme IV).