(1S,4aS,6S,8aS)-8a-Methyl-perhydronaphthalin-1,6-diol | 65137-57-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,4aS,6S,8aS)-8a-Methyl-perhydronaphthalin-1,6-diol
• 英文别名: 1β,6β-Dihydroxy-8aβ-methyl-1,2,3,4,4aα,5,6,7,8,8a-decahydronaphthalin；3β,8β-Dihydroxy-8aβ-methyl-trans-dekalin; 10β-Methyl-trans-decalin-3β,9β-diol；(4aS)-8a-methyl-(4ar,8at)-decahydro-naphthalene-1t,6t-diol；(4aS)-8a-Methyl-(4ar,8at)-decahydro-naphthalin-1t,6t-diol；(1S,4aS,6S,8aS)-8a-methyl-2,3,4,4a,5,6,7,8-octahydro-1H-naphthalene-1,6-diol
• CAS: 65137-57-7
• 化学式: C₁₁H₂₀O₂
• 分子量: 184.279
• InChiKey: MPZJXFSZLAPMGN-NAKRPEOUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1S,4aS,6S,8aS)-8a-Methyl-perhydronaphthalin-1,6-diol 在 chromium(VI) oxide 、 硫酸 、 丙酮 作用下， 生成 trans-8a-methyldecahydronaphthalene-1,6-dione
  参考文献：
  名称：

  与微生物反应。第十次沟通。镰刀菌减少（±）-9-甲基-反式-地卡林二酮-（1,6）

  摘要：

  镰刀菌（TEHON）BOEDIJN在位置1和位置6迅速还原（9 S）-9-甲基-反式-癸二酮- （1,6）（IV），形成羟基酮V和VI（和对映异构体）起始原料的（9 R）-对映异构体的进攻更慢，主要形成羟基酮IX（和IX的对映异构体）。

  DOI：

  10.1002/hlca.19590420615
• 作为产物：
  描述：

  (S)-(+)-3,4,8,8a-四氢-8a-甲基-1,6-(2H,7H)-萘醌 在 sodium tetrahydroborate 作用下， 生成 (1S,4aS,6S,8aS)-8a-Methyl-perhydronaphthalin-1,6-diol
  参考文献：
  名称：

  [（+）-D-高雌酮3-甲基醚的全合成（作者翻译）]。

  摘要：

  Total Synthesis of (+)‐D‐Homoestrone 3‐methyl etherA novel total synthesis of (+)‐D‐homoestrone 3‐methyl ether (21) is described starting from (S)‐8a‐methyl‐3,4,8,8a‐tetrahydro‐2H, 7H‐naphthalene‐1,6‐dione (1) as a chiral synthon for the rings C and D. The key step involves alkylation of the derived 3 with m‐methoxyphenacyl bromide (4) as an AB‐building block to give the dioxo‐secosteroid 5. Hydrogenation of 5 affords the trans‐decalone 11. As by‐products the epimeric cis‐decalones 12 and 13 were characterized. Cyclization of 11 leads under kinetic control predominantly to the Δ9(11)‐tetraene 14. Catalytic hydrogenation of 14 and subsequent modification in ring D give the title compound 21. It was found that 14 and also the derived Δ8‐isomer 15a add hydrogen from the α‐face of the molecule to an extent of about 80%. The 8α‐D‐homoestrone derivatives 20a and 23 as well as the 9β‐isomers 19a and 22 were characterized.

  DOI：

  10.1002/hlca.19770600717

文献信息

• Birch et al., Journal of the Chemical Society, 1958, p. 4688,4691
  作者：Birch et al.

  DOI：——

  日期：——
• 535. The reduction of 9-methyl-Δ⁵⁽¹⁰⁾-octalin-1,6-dione
  作者：C. B. C. Boyce、J. S. Whitehurst

  DOI：10.1039/jr9600002680

  日期：——
• Reaktionen mit Mikroorganismen. 10. Mitteilung. Die Reduktion von (±)-9-Methyl-<i>trans</i>-dekalindion-(1,6) mit<i>Curvularia falcata</i>
  作者：V. Prelog、D. Zäch

  DOI：10.1002/hlca.19590420615

  日期：——

  Curvularia falcata (TEHON) BOEDIJN reduziert das (9S)-9-Methyl-trans-dekalindion-(l,6) (IV) rasch, sowohl in Stellung 1 als auch in Stellung 6, unter Bildung von Hydroxyketonen V und VI (und Enantiomeres von VI) und von Diol VII. Das (9R)-Enantiomere des Eduktes wird langsamer angegriffen, wobei hauptsächlich das Hydroxyketon IX (und Enantiomeres von IX) und das Diol X entstehen.

  镰刀菌（TEHON）BOEDIJN在位置1和位置6迅速还原（9 S）-9-甲基-反式-癸二酮- （1,6）（IV），形成羟基酮V和VI（和对映异构体）起始原料的（9 R）-对映异构体的进攻更慢，主要形成羟基酮IX（和IX的对映异构体）。
• Totalsynthese von (+)-<i>D</i>-Homoöstron-3-methyläther
  作者：Jürg Gutzwiller、Werner Meier、Andor Fürst

  DOI：10.1002/hlca.19770600717

  日期：1977.11.2

  Total Synthesis of (+)‐D‐Homoestrone 3‐methyl etherA novel total synthesis of (+)‐D‐homoestrone 3‐methyl ether (21) is described starting from (S)‐8a‐methyl‐3,4,8,8a‐tetrahydro‐2H, 7H‐naphthalene‐1,6‐dione (1) as a chiral synthon for the rings C and D. The key step involves alkylation of the derived 3 with m‐methoxyphenacyl bromide (4) as an AB‐building block to give the dioxo‐secosteroid 5. Hydrogenation of 5 affords the trans‐decalone 11. As by‐products the epimeric cis‐decalones 12 and 13 were characterized. Cyclization of 11 leads under kinetic control predominantly to the Δ9(11)‐tetraene 14. Catalytic hydrogenation of 14 and subsequent modification in ring D give the title compound 21. It was found that 14 and also the derived Δ8‐isomer 15a add hydrogen from the α‐face of the molecule to an extent of about 80%. The 8α‐D‐homoestrone derivatives 20a and 23 as well as the 9β‐isomers 19a and 22 were characterized.