4,4a,5,6,7,8-Hexahydro-1-methoxy-4a-methyl-2(3H)-naphthalinone | 43042-62-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4,4a,5,6,7,8-Hexahydro-1-methoxy-4a-methyl-2(3H)-naphthalinone
• 英文别名: 1-Methoxy-10-methyl-1,9-octalin-2-on；1-Methoxy-4a-methyl-3,4,5,6,7,8-hexahydro-naphthalen-2-one；1-methoxy-4a-methyl-3,4,5,6,7,8-hexahydronaphthalen-2-one
• CAS: 43042-62-2
• 化学式: C₁₂H₁₈O₂
• 分子量: 194.274
• InChiKey: OKFRCXUYSLLRCL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4,4a,5,6,7,8-Hexahydro-1-methoxy-4a-methyl-2(3H)-naphthalinone 在 吡啶 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 作用下， 以 乙醚 、 二甲基亚砜 为溶剂， 反应 12.0h， 生成 3,4,4a,5,6,7-hexahydro-4a-methyl-1(2H)-naphthalenone
  参考文献：
  名称：

  Stereoselective synthesis of cyclopentanones by reductive cleavage of 6-oxonorbornane-2-carboxylates and its application to the synthesis of 1.alpha.,25-dihydroxyvitamin D3 CD ring

  摘要：

  A novel chiral synthesis of the CD-ring 2 of 1alpha,25-dihydroxyvitamin D3 (1a) is described. The optically active D-ring keto ester 3c was prepared by reductive cleavage of 6-oxonorbornane-2-carboxylate 4c with lithium naphthalenide. 1,2-Transposition of enone 15, which was obtained by Robinson annulation of 14, was accomplished via thermolysis of the allylic carbonate 29 at 100-degrees-C to give enone 16. Reduction of ketone 16 with NaBH4-CeCl3 followed by hydrogenation with RhCl-(PPh3)3 catalyst gave trans-indanol 32, which was transformed to intermediate 2.

  DOI：

  10.1021/jo00058a032
• 作为产物：
  描述：

  4A-甲基-4,4a,5,6,7,8-六氢-3H-萘-2-酮 在 氢氧化钾 、 sodium hydroxide 、 双氧水 作用下， 以 甲醇 为溶剂， 生成 4,4a,5,6,7,8-Hexahydro-1-methoxy-4a-methyl-2(3H)-naphthalinone
  参考文献：
  名称：

  Stereoselective synthesis of cyclopentanones by reductive cleavage of 6-oxonorbornane-2-carboxylates and its application to the synthesis of 1.alpha.,25-dihydroxyvitamin D3 CD ring

  摘要：

  A novel chiral synthesis of the CD-ring 2 of 1alpha,25-dihydroxyvitamin D3 (1a) is described. The optically active D-ring keto ester 3c was prepared by reductive cleavage of 6-oxonorbornane-2-carboxylate 4c with lithium naphthalenide. 1,2-Transposition of enone 15, which was obtained by Robinson annulation of 14, was accomplished via thermolysis of the allylic carbonate 29 at 100-degrees-C to give enone 16. Reduction of ketone 16 with NaBH4-CeCl3 followed by hydrogenation with RhCl-(PPh3)3 catalyst gave trans-indanol 32, which was transformed to intermediate 2.

  DOI：

  10.1021/jo00058a032

文献信息

• .alpha.-Methoxylation of Unsaturated Carbonyl Compounds
  作者：Albert Feuerer、Theodor Severin

  DOI：10.1021/jo00099a037

  日期：1994.10

  alpha-Methoxylation of enals or enones can be performed in high yield by a simple one-pot reaction sequence: Bromination of unsaturated hydrazones, HBr-elimination, and addition of methanol leads to the formation of beta-bromo-alpha-methoxy hydrazones (11), which after hydrolysis and HBr-elimination yields the alpha-methoxy enals or alpha-methoxy enones (13), respectively.
• Wenkert,E. et al., Synthetic Communications, 1973, vol. 3, p. 205 - 209
  作者：Wenkert,E. et al.

  DOI：——

  日期：——
• Feuerer Albert, Severin Theodor, J. Org. Chem, 59 (1994) N 20, S 6026-6029
  作者：Feuerer Albert, Severin Theodor

  DOI：——

  日期：——
• Stereoselective synthesis of cyclopentanones by reductive cleavage of 6-oxonorbornane-2-carboxylates and its application to the synthesis of 1.alpha.,25-dihydroxyvitamin D3 CD ring
  作者：Kazuo Nagasawa、Naoto Matsuda、Yasuo Noguchi、Masahiro Yamanashi、Yoshiro Zako、Isao Shimizu

  DOI：10.1021/jo00058a032

  日期：1993.3

  A novel chiral synthesis of the CD-ring 2 of 1alpha,25-dihydroxyvitamin D3 (1a) is described. The optically active D-ring keto ester 3c was prepared by reductive cleavage of 6-oxonorbornane-2-carboxylate 4c with lithium naphthalenide. 1,2-Transposition of enone 15, which was obtained by Robinson annulation of 14, was accomplished via thermolysis of the allylic carbonate 29 at 100-degrees-C to give enone 16. Reduction of ketone 16 with NaBH4-CeCl3 followed by hydrogenation with RhCl-(PPh3)3 catalyst gave trans-indanol 32, which was transformed to intermediate 2.