exo-3-hydroxy-exo-2-(β-naphthyl)bornane | 144764-79-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: exo-3-hydroxy-exo-2-(β-naphthyl)bornane
• CAS: 144764-79-4
• 化学式: C₂₀H₂₄O
• 分子量: 280.41
• InChiKey: YGDPUBJTNPAWIL-MLYOOKFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.74
• 重原子数：
  21.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  exo-3-hydroxy-exo-2-(β-naphthyl)bornane 在 4-二甲氨基吡啶 、 4 A molecular sieve 、 thallium (I) ethoxide 、 potassium carbonate 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 31.5h， 生成 2-Dimethoxymethyl-2-hydroxy-1,3-dimethyl-4-oxo-cyclohexanecarboxylic acid (1S,2R,3S,4S)-4,7,7-trimethyl-3-naphthalen-2-yl-bicyclo[2.2.1]hept-2-yl ester
  参考文献：
  名称：

  Enantioselective syntheses and resolution of the key white intermediate for the synthesis of trisporic acids

  摘要：

  Two asymmetric syntheses of the alkylated cyclohexenone carboxylic acid moiety, the key White intermediate (4a), of trisporic acids A, B and C are described. The syntheses feature a Michael addition in tandem with an aldol condensation as the central step. The resolution of this readily available intermediate is also described. Copyright (C) 1996 Elsevier Science

  DOI：

  10.1016/0957-4166(96)00109-7

文献信息

• Asymmetric induction in Manganese(III)-based oxidative free-radical cyclizations of chiral esters and amides
  作者：Barry B. Snider、Qingwei Zhang

  DOI：10.1016/s0040-4039(00)61089-4

  日期：1992.9

  Mn(III)-based oxidative free-radical cyclizations of phenylmenthyl acetoacetate 1d affords 90% of 11 with 86% de. trans-2-Phenylcyclohexyl ester 1e affords 5e with only 60% de. The 2,5-dimethylpyrrolidine amide 1h affords 14 with higher de (92%), but in only 28% yield.

  乙酰薄荷基乙酸薄荷酯1d的基于Mn（III）的氧化自由基环化反应得到90％的11和86％的de。反式-2-苯基环己基酯1e得到的de只有60％的5e。2,5-二甲基吡咯烷酰胺1H，得到14具有较高的德（92％），但在仅28％的产率。
• Asymmetric induction in manganese(III)-based oxidative free-radical cyclizations of phenylmenthyl acetoacetates and 2,5-dimethylpyrrolidine acetoacetamides
  作者：Qingwei Zhang、Raju M. Mohan、Laura Cook、Sophia Kazanis、Daniel Peisach、Bruce M. Foxman、Barry B. Snider

  DOI：10.1021/jo00079a006

  日期：1993.12

  Mn(III)-based oxidative free-radical cyclization of phenylmenthyl ester 1e afforded 90% of 13 with 86% de. Cyclization of 31b provided 56% of (+)-podocarpic acid precursor 32e with 82% de. The direction of de was opposite in these two cases. Oxidative cyclization of a-methyl beta-keto ester 44b gave a 1:1.6 mixture of 46b and 47b while alpha-propyl beta-keto ester 44d produced a > 10:1 mixture of 46d and 47d indicating that the extent and direction of de is dependent on the size of the alpha-substituent The reaction proceeds through transition states 12 and 56 with large alpha-substituents and through transition states 19 and 57 with small a-substituents. The de depends on the double-bond substitution pattern as shown by the decreased de with 37b and 37d, and selectivity in the 5-exo cyclization of 64b, 65b, 70b, and 71b is low.