(3R,4S)-3-ethyl-3-hydroxy-4-(hydroxy)methyl-8-methoxy-1,2,3,4-tetrahydronaphtahlene | 139686-37-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (3R,4S)-3-ethyl-3-hydroxy-4-(hydroxy)methyl-8-methoxy-1,2,3,4-tetrahydronaphtahlene
• 英文别名: (1S,2R)-2-ethyl-1-(hydroxymethyl)-5-methoxy-3,4-dihydro-1H-naphthalen-2-ol
• CAS: 139686-37-6
• 化学式: C₁₄H₂₀O₃
• 分子量: 236.311
• InChiKey: ZZLJIIISDFJKDK-TZMCWYRMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-ethyl-5-methoxy-1-tetralone 在 (+)-(8,8-dichlorocamphorylsulfonyl)-oxaziridine 、 alkaline hydrogen peroxide 、 硫酸 、 氯化铵 、 diborane(6) 、 lithium diisopropyl amide 作用下， 反应 26.0h， 生成 (3R,4S)-3-ethyl-3-hydroxy-4-(hydroxy)methyl-8-methoxy-1,2,3,4-tetrahydronaphtahlene
  参考文献：
  名称：

  aklavinone ab环的不对称合成

  摘要：

  aklavinone 3的AB环的正式合成是通过三步法从四氢萘酮5制备的二醇8的不对称合成而实现的。关键步骤涉及使用（樟脑磺酰基）恶唑烷衍生物（+）- 4b在≥95％ee中5的不对称羟基化。

  DOI：

  10.1016/0040-4039(91)80561-j

文献信息

• Enantio- and diastereoselective synthesis of the AB ring system of aklavinone by coupling a chemoenzymatic procedure with organometal chemistry
  作者：Luca Banfi、Giuseppe Guanti、Renata Riva

  DOI：10.1016/0040-4020(96)00804-6

  日期：1996.10

  Two different approaches were investigated in order to prepare the title compound 2; best results were obtained when the tandem reduction/intramolecular hydroxyalkylation of the appropriate 5-alkoxy-(3-hydroxyphenyl)pentanoate was performed on an ester of chemoenzymatic origin, already bearing the two chiral centers present in 2 with the correct relative and absolute stereochemistry.

  为了制备标题化合物2，研究了两种不同的方法; 当在化学酶促来源的酯进行了适当的5-烷氧基- （3-羟基苯基）戊酸甲酯的串联还原/分子内羟烷基化，已经承载两个手性中心存在于得到最佳结果2具有正确的相对和绝对立体化学。
• Enantioselective synthesis of the AB ring system of aklavinone via a chemoenzymatic route
  作者：Giuseppe Guanti、Renata Riva

  DOI：10.1016/0040-4039(95)00645-s

  日期：1995.5

  The AB ring system 2 of aklavinone 1 was obtained using a chemoenzymatic protocol. Key steps are the stereoselective addition of lithium enolate of ethyl acetate to ketone 13 and the intramolecular Friedel-Crafts reaction to give tetralin 17.
• Asymmetric synthesis of the ab-ring of aklavinone
  作者：Franklin A. Davis、Anil Kumar

  DOI：10.1016/0040-4039(91)80561-j

  日期：1991.12

  A formal synthesis of the AB-ring of aklavinone 3 was achieved via the asymmetric synthesis of diol 8 prepared in three steps from tetralone 5. The crucial step involved the asymmetric hydroxylation of 5 in ≥ 95% ee using (camphorylsulfonyl)oxaziridine derivative (+)-4b.

  aklavinone 3的AB环的正式合成是通过三步法从四氢萘酮5制备的二醇8的不对称合成而实现的。关键步骤涉及使用（樟脑磺酰基）恶唑烷衍生物（+）- 4b在≥95％ee中5的不对称羟基化。