cis-10a-hydroxy-5-methoxy-4a-methyl-3,4,4a,9,10,10a-hexahydrophenanthren-1(2H)-one | 68946-64-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: cis-10a-hydroxy-5-methoxy-4a-methyl-3,4,4a,9,10,10a-hexahydrophenanthren-1(2H)-one
• 英文别名: (4aR,10aR)-10a-hydroxy-5-methoxy-4a-methyl-3,4,9,10-tetrahydro-2H-phenanthren-1-one
• CAS: 68946-64-5
• 化学式: C₁₆H₂₀O₃
• 分子量: 260.333
• InChiKey: QFKDOIKCDKVTDP-CVEARBPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.38
• 重原子数：
  19.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  cis-10a-hydroxy-5-methoxy-4a-methyl-3,4,4a,9,10,10a-hexahydrophenanthren-1(2H)-one 、 硼氢化钠 生成 (4aR,10aR)-5-Methoxy-4a-methyl-2,3,4,4a,9,10-hexahydro-1H-phenanthrene-1,10a-diol
  参考文献：
  名称：

  AMUPITAN, J. A.;HUQ, E.;MELLOR, M.;SCOVELL, E. G.;SUTHERLAND, J. K., J. CHEM. SOC. PERKIN TRANS., 1983, N 4, 751-753

  摘要：

  DOI：
• 作为产物：
  描述：

  1-[2-(4-Methoxy-phenyl)-ethyl]-6-methyl-7-oxa-bicyclo[4.1.0]heptan-2-one 在 三氟化硼乙醚 作用下， 生成 cis-10a-hydroxy-5-methoxy-4a-methyl-3,4,4a,9,10,10a-hexahydrophenanthren-1(2H)-one
  参考文献：
  名称：

  一些环氧烯烃环化

  摘要：

  已经表明，某些烷基-2-烯基-2,3-环氧-3-甲基环己酮可以与一些路易斯酸以良好的产率环化成十萘醌衍生物，但是使用弱路易斯酸和/或非极性溶剂会导致环收缩。

  DOI：

  10.1039/c39780000526

文献信息

• 3-Methylcyclohex-2-enone derivatives as initiators of cyclisation. Part 2. Monocyclisations to six-membered rings
  作者：Joseph A. Amupitan、Enamul Huq、Michael Mellor、Edward G. Scovell、James K. Sutherland

  DOI：10.1039/p19830000751

  日期：——

  Cyclisation of 3-methylcyclohex-2-enones and the derived epoxides containing alkene, alkyne, and aryl side-chains yields bicyclo[4.4.0]decane derivatives when the alkene or alkyne is electronically biased towards six-membered ring formation and when the alkene is electronically unbiased.

  当烯或炔被电子偏向六元环形成且烯被电子偏置时，3-甲基环己-2-烯酮和衍生的含烯烃，炔和芳基侧链的环氧化物的环化反应会生成双环[4.4.0]癸烷衍生物电子无偏。
• Cationic cyclization of keto-epoxides mediated by zirconium(IV) tetrachloride: diastereoselective synthesis of cis-decalinols
  作者：Sylvie Goncalves、Marc Nicolas、Philippe Maillos、Rachid Baati

  DOI：10.1016/j.tet.2011.08.050

  日期：2011.10

  10-Methyl-cis-9-decalinols are important motifs in several natural products and key intermediates in total synthesis. Herein, we wish to describe a highly chemo- and diastereoselective cyclization of ketoepoxides leading to 10-methyl-cis-9-decalinols. This method based on the use of zirconium(IV) tetrachloride permits the access to a wide variety of cis-decalinols in good to excellent yields. The cationic cyclization could also be performed with chiral keto-epoxide with complete control of the diastereoselectivity affording cis-bicyclic tertiary alcohol with good enantiomeric excess. The chemo- and the diastereoselectivity are assumed to result from the ability of Zr(IV) to generate highly stable bidentic complexes with alpha-hydroxy-ketone intermediates. (C) 2011 Elsevier Ltd. All rights reserved.
• HUQ E.; MELLOR M.; SCOVELL E. G.; SUTHERLAND J. K., J. CHEM. SOC. CHEM. COMMUN., 1978, NO 13, 526-528
  作者：HUQ E.、 MELLOR M.、 SCOVELL E. G.、 SUTHERLAND J. K.

  DOI：——

  日期：——