1-hydroxy-1-methyl-1,2,3,4,6,9-hexahydronaphthalene | 103094-38-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-hydroxy-1-methyl-1,2,3,4,6,9-hexahydronaphthalene
• 英文别名: 1-hydroxy-1-methyl-1,2,3,4,6,9-hexahydronaphtalene；trans-1-methyl-1,2,3,4,6,8a-hexahydro-1-naphthol；(1R,8aR)-1-methyl-3,4,6,8a-tetrahydro-2H-naphthalen-1-ol
• CAS: 103094-38-8；144127-35-5
• 化学式: C₁₁H₁₆O
• 分子量: 164.247
• InChiKey: IEAGQNQECOWMCL-GHMZBOCLSA-N

物化性质

• 熔点：
  102-103 °C(Solv: carbon tetrachloride (56-23-5))
• 沸点：
  272.8±9.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-hydroxy-1-methyl-1,2,3,4,6,9-hexahydronaphthalene 生成 (±)-1-methyl-1-decalol
  参考文献：
  名称：

  SHONO TATSUYA; KISE NAOKI; SUZUMOTO TAKESHI; MORIMOTO TOSHIO, J. AMER. CHEM. SOC., 108,(1986) N 15, 4676-4677

  摘要：

  DOI：
• 作为产物：
  描述：

  5-苯基戊烷-2-酮 在 DMP⁽¹⁺⁾*BF₄^(1-) 作用下， 以80%的产率得到1-hydroxy-1-methyl-1,2,3,4,6,9-hexahydronaphthalene
  参考文献：
  名称：

  由（二甲基吡咯烷基）汞介导的酮的电化学还原。不饱和酮的还原环化和氧化还原催化研究

  摘要：

  Etude de la 还原electrochimique et cyclisation de l'heptene-6one-2 a une 电极 de mercure dans le DMF

  DOI：

  10.1021/ja00219a042

文献信息

• Samarium Diiodide Mediated Ketyl-Aryl Coupling Reactions - Influence of Substituents and Trapping Experiments
  作者：Ulrike K. Wefelscheid、Mathias Berndt、Hans-Ulrich Reißig

  DOI：10.1002/ejoc.200800293

  日期：2008.7

  derivatives as single diastereoisomers in most cases. The position of the substituents was also of crucial influence on the outcome; in several cases ipso-substitution leading to the formation of spiro compounds was observed. Electron-donating substituents at the aromatic moiety are less favourable for the ketyl–aryl couplings. They apparently impede the second electron transfer that is involved in this multi-step

  这项综合研究描述了芳基部分的取代基对 SmI2 介导的分子内酮基-芳基偶联反应的影响。不同取代的γ-芳基酮被用作前体，其通过4-戊烯-2-醇与相应的溴苯或碘苯的Heck反应直接制备。在用两当量的二碘化钐γ-芳基酮处理后，带有吸电子取代基，如氰基、三氟甲基或羰基，在大多数情况下，得到预期的六氢化萘衍生物，为单一的非对映异构体。取代基的位置对结果也有至关重要的影响。在一些情况下，观察到导致形成螺环化合物的 ipso 取代。芳族部分的给电子取代基对酮基-芳基偶联不太有利。它们显然阻碍了这个多步骤过程中涉及的第二次电子转移。在这些观察的基础上，详细讨论了 促进的酮基-芳基偶联的机制。对于在间位具有吸电子取代基的前体， 促进的环化的相当稳定的碳负离子中间体可以用丙酮或烯丙基溴作为亲电试剂捕获，以区域选择性地提供相应的加成产物。我们的结果对于立体选择性生成的六氢化萘衍生物的合成应用应该是有价值的。（©
• Electroorganic chemistry. 98. Novel intramolecular stereoselective addition of electrogenerated radical species to the aromatic ring
  作者：Tatsuya. Shono、Naoki. Kise、Takeshi. Suzumoto、Toshio. Morimoto

  DOI：10.1021/ja00275a084

  日期：1986.7

  La reduction electrochimique de derives de l'aryl-5 pentanone-2 conduit a des derives de l'(hexahydro-1,2,3,4,6,8a methyl-1) naphtol-1

  La 还原电化学 de 衍生 de l'aryl-5 pentanone-2 导管 a des 衍生 de l'(hexahydro-1,2,3,4,6,8amethyl-1)naphtol-1
• Theoretical Study of Electroreductive Intramolecular Coupling of Nonconjugated Olefinic and Aromatic Ketones
  作者：Naoki Kise

  DOI：10.1021/jo0356255

  日期：2004.3.1

  The electroreductive cyclization of hept-6-en-2-one, octa-7-en-2-one, and 5-phenylpentan-2-one was investigated by ab initio (UHF/6-311++G**) and density functional (UB3LYP/6-311++G**) calculation methods. The high regio- and stereoselectivities previously reported for olefinic ketones (exo-trans) and 5-arylpentan-2-ones (endo-trans) were reconfirmed. These experimental results well agree with the

  从头开始（UHF / 6-311 ++ G **）研究了庚6-烯-2-酮，八烯-7-烯-2-酮和5-苯基戊烷-2-酮的电还原环化反应密度函数（UB3LYP / 6-311 ++ G **）计算方法。再次证实了先前报道的烯烃酮（exo-trans）和5-芳基戊烷-2-one（endo-trans）的高区域选择性和立体选择性。这些实验结果与通过单电子转移至酮产生的酮基的分子内偶联中的过渡态的计算结果完全吻合。
• Electroorganic Chemistry. 144. Electroreductive Coupling of Ketones with O-Methyl Oximes, N,N-Dimethylhydrazones, and Nitrones. A Convenient Route to Synthesis of .beta.-Amino Alcohol
  作者：Tatsuya Shono、Naoki Kise、Taku Fujimoto、Ayuko Yamanami、Ryoji Nomura

  DOI：10.1021/jo00086a023

  日期：1994.4

  The intermolecular coupling of a variety of ketones with some types of O-methyl oximes took place when a mixture of both components was electrochemically reduced in i-PrOH with an Sn cathode. The product, beta-methoxyamino alcohol was easily converted to beta-amino alcohol by simple reduction. A chiral ligand effective for the enantioselective addition of diethylzinc to an aldehyde was easily obtained from the product formed by the electroreductive coupling of (-)-menthone with O-methylacetaldoxime. The intermolecular coupling of a ketone with a N,N-dimethylhydrazone or nitrone was also promoted by the electroreduction. Furthermore, the electroreductive coupling of a carbonyl group with an intramolecular O-methyl oxime moiety gave the corresponding cyclized product stereoselectively.
• Electroreductive intramolecular coupling of nonconjugated aromatic ketones
  作者：Naoki Kise、Takeshi Suzumoto、Tatsuya Shono

  DOI：10.1021/jo00085a033

  日期：1994.3

  The electroreduction of nonconjugated aromatic ketones gave intramolecularly coupled products. The best result was obtained using an Sn cathode in i-PrOH containing tetraalkylammonium salt as a supporting electrolyte. This reductive cyclization proceeded with remarkable stereoselectivity, and the cis isomer was obtained exclusively. A variety of new bi- and polycyclic compounds were synthesized. The reaction mechanism was studied, and it was suggested that the anion radical generated by one-electron transfer to a carbonyl group attacks an aromatic ring intramolecularly. The choice of counter cation of the anion radical was critical for the reductive cyclization. Other reductive methods employing metal reducing agents were also studied. Reduction with Na in HMPA-THF gave the same cyclized product, though the yield was lower than that with the electroreduction.