(1R,6S,7S)-7-<<((R)-1-(2,4-dichlorophenoxy)ethyl)carbonyl>oxy>-9-methylenebicyclo<4.3.0>nonane | 144303-42-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1R,6S,7S)-7-<<((R)-1-(2,4-dichlorophenoxy)ethyl)carbonyl>oxy>-9-methylenebicyclo<4.3.0>nonane
• 英文别名: (1R,6S,7S)-7-propoxy-9-methylenebicyclo<4.3.0>nonane；[(1S,3aR,7aS)-3-methylidene-1,2,3a,4,5,6,7,7a-octahydroinden-1-yl] (2R)-2-(2,4-dichlorophenoxy)propanoate
• CAS: 144303-42-4
• 化学式: C₁₉H₂₂Cl₂O₃
• 分子量: 369.288
• InChiKey: CJRKTMFPYCAPRM-FHIHXZLISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  cis-1,2-divinylocyclohexane 、 (R)-2-(2,4-二氯苯氧基)丙酸 在 manganese(IV) oxide 、 palladium diacetate 、 molecular sieve 、 对苯醌 作用下， 以 丙酮 为溶剂， 生成 (1R,6S,7S)-7-<<((R)-1-(2,4-dichlorophenoxy)ethyl)carbonyl>oxy>-9-methylenebicyclo<4.3.0>nonane 、 (1S,6R,7R)-7-<<((R)-1-(2,4-dichlorophenoxy)ethyl)carbonyl>oxy>-9-methylenebicyclo<4.3.0>nonane
  参考文献：
  名称：

  Use of molecular sieves for promotion of diastereoselectivity in palladium-catalysed oxidative cyclisation. Reversal of diastereofacial selectivity

  摘要：

  分子筛对顺式-1,2-二乙烯基环己烷的氧化环化具有决定性的影响，从而提高了非对映选择性（17-62%），并偶尔使新生成的手性中心的绝对构型相反。

  DOI：

  10.1039/c39910000218

文献信息

• Use of molecular sieves for promotion of diastereoselectivity in palladium-catalysed oxidative cyclisation. Reversal of diastereofacial selectivity
  作者：Andreas Heumann、Louise Tottie、Christina Moberg

  DOI：10.1039/c39910000218

  日期：——

  Molecular sieves have a decisive influence on the oxidative cyclisation of cis-1,2-divinylcyclohexane, resulting in enhanced diastereoselectivity (17–62%) as well as, occasionally, in opposite absolute configuration of the newly created chiral centres.

  分子筛对顺式-1,2-二乙烯基环己烷的氧化环化具有决定性的影响，从而提高了非对映选择性（17-62%），并偶尔使新生成的手性中心的绝对构型相反。
• Molecular sieve controlled diastereoselectivity: effect in the palladium-catalyzed cyclization of cis-1,2-divinylcyclohexane with .alpha.-oxygen-substituted acids as chiral nucleophiles
  作者：Louise Tottie、Peter Baeckstroem、Christina Moberg、Joergen Tegenfeldt、Andreas Heumann

  DOI：10.1021/jo00050a039

  日期：1992.11

  Molecular sieves have been shown to improve greatly the stereoselectivity in the palladium(II)-catalyzed reaction of cis-1,2-divinylcyclohexane with chiral acids. Reactions run with molecular sieves and derivatives of (R)-lactic acids as nucleophiles always yielded products with S configuration at the newly formed chiral center in contrast to reactions without molecular sieves that gave products with either S or R configuration at this chiral center. It appears that this effect has not been observed previously. Only water-containing molecular sieves increased the stereoselectivity. A chiral palladium complex was formed faster in the presence of molecular sieves, but use of this complex as catalyst in the cyclization did not result in increased selectivity. The best stereoselectivity was found for molecular sieves with a high sodium content (Lancaster 13X and 4-angstrom sieves).