cis-9-Hydroxy-10-methyl-dekalin-2,5-dion | 35537-88-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: cis-9-Hydroxy-10-methyl-dekalin-2,5-dion
• 英文别名: (4aS,8aS)-4a-hydroxy-8a-methyl-2,3,4,5,7,8-hexahydronaphthalene-1,6-dione
• CAS: 35537-88-3
• 化学式: C₁₁H₁₆O₃
• 分子量: 196.246
• InChiKey: AUQCZCQROHUVBU-MNOVXSKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  cis-9-Hydroxy-10-methyl-dekalin-2,5-dion 以 乙醚 为溶剂， 以101.2 g的产率得到(S)-(+)-3,4,8,8a-四氢-8a-甲基-1,6-(2H,7H)-萘醌
  参考文献：
  名称：

  (S)-8a-METHYL-3,4,8,8a-TETRAHYDRO-1,6(2H, 7H)-NAPHTHALENEDIONE

  摘要：

  DOI：

  10.15227/orgsyn.063.0037
• 作为产物：
  描述：

  2-甲基-1,3-环己二酮 在 对苯二酚 、 L-脯氨酸 作用下， 以 水 、 溶剂黄146 、 二甲基亚砜 为溶剂， 反应 121.0h， 生成 cis-9-Hydroxy-10-methyl-dekalin-2,5-dion
  参考文献：
  名称：

  (S)-8a-METHYL-3,4,8,8a-TETRAHYDRO-1,6(2H, 7H)-NAPHTHALENEDIONE

  摘要：

  DOI：

  10.15227/orgsyn.063.0037

文献信息

• Proline imidazolidinones and enamines in Hajos–Wiechert and Wieland–Miescher ketone synthesis
  作者：Ángel L. Fuentes de Arriba、Luis Simón、César Raposo、Victoria Alcázar、Joaquín R. Morán

  DOI：10.1016/j.tet.2009.04.050

  日期：2009.6

  from the acid chloride of proline hydrochloride and anilines induce large enantiomeric excesses in intramolecular aldol condensations. Imidazolidinones derived from the reaction of the catalyst and enamines have been found as intermediates in these reactions.

  从脯氨酸盐酸盐的酰氯和苯胺获得的现成的芳香族脯氨酰胺在分子内羟醛缩合中引起大量的对映体过量。已经发现衍生自催化剂和烯胺的反应的咪唑烷酮是这些反应的中间体。
• A new diagnostic tool for elucidating the mechanism of enantioselective reactions. Application to the Hajos–Parrish reaction
  作者：Claude Agami、Jacques Levisalles、Catherine Puchot

  DOI：10.1039/c39850000441

  日期：——

  A dilution effect shows that the proline-catalysed Robinson cyclisation involves both enantioselective and non-enantioselective processes, with a different dependence on amino acid concentration.

  稀释作用表明脯氨酸催化的罗宾逊环化涉及对映选择性和非对映选择性过程，对氨基酸浓度的依赖性不同。
• Bifunctional organocatalysts based on a carbazole scaffold for the synthesis of the Hajos–Wiechert and Wieland–Miescher ketones
  作者：Omayra H. Rubio、Ángel L. Fuentes de Arriba、Laura M. Monleón、Francisca Sanz、Luis Simón、Victoria Alcázar、Joaquín R. Morán

  DOI：10.1016/j.tet.2014.12.079

  日期：2015.2

  Several bifunctional organocatalysts based on a carbazole scaffold containing a chiral amine and a synthetic oxyanion-hole have been synthesized and successfully applied to the synthesis of the Hajos-Wiechert and Wieland-Miescher ketones (up to 99% ee). Both enamine activation and H-bonding donor ability of these catalysts were evaluated by preparing catalysts differing in the nature of the amine [(R,R)-cyclohexanediamine or L-proline], the H-bond donor functional group (sulfonamide or amide) and the number of NH bonds. Modeling studies and an X-ray structure fully support the obtained results. (C) 2015 Elsevier Ltd. All rights reserved.
• Asymmetric one-pot Robinson annulations
  作者：D Rajagopal、R Narayanan、S Swaminathan

  DOI：10.1016/s0040-4039(01)00733-x

  日期：2001.7

  One-pot syntheses of ketol SS-5a, enone S-2 and optically active spiroenediones S-14. R-7 and S-15 are reported. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Stereochemical Course of the Robinson Annelation Reaction. cis-9-Hydroxy-10-methyldecalin-2,5-dione
  作者：Thomas A. Spencer、Hartley S. Neel、David C. Ward、Kenneth L. Williamson

  DOI：10.1021/jo01340a019

  日期：1966.2