(4as,8ar)-8a-methyloctahydronaphthalen-4a(2H)-ol | 5173-74-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4as,8ar)-8a-methyloctahydronaphthalen-4a(2H)-ol
• 英文别名: cis-6-methylbicyclo<4.3.0>decan-1-ol；6-methylbicyclo<4.4.0>dodecan-1-ol；8a-methyl-cis-decahydronaphthalen-4a-ol；cis-10-methyl-9-decalol；9-hydroxy-10-methyl-cis-decalin；4aβ-Methyl-dekahydronaphthol-(8aβ)；5α-Hydroxy-10α-methyldecalin
• CAS: 5173-74-0
• 化学式: C₁₁H₂₀O
• 分子量: 168.279
• InChiKey: UWRUMJPLZZBUCM-XYPYZODXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.87
• 重原子数：
  12.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (4as,8ar)-8a-methyloctahydronaphthalen-4a(2H)-ol 在 碘 、 mercury(II) oxide 作用下， 以 吡啶 、 苯 为溶剂， 反应 2.0h， 生成 (E)-6-methylcyclodec-5-enone 、 (Z)-6-methylcyclodec-5-enone
  参考文献：
  名称：

  Suginome, Hiroshi; Kondoh, Takahiko; Gogonea, Camelia, Journal of the Chemical Society. Perkin transactions I, 1995, # 1, p. 69 - 82

  摘要：

  DOI：
• 作为产物：
  描述：

  10-methyl-Δ^1,9-octalin 在 platinum(IV) oxide 、 lithium aluminium tetrahydride 、 氢气 、 氧气 、 rose bengal 作用下， 以 吡啶 、 乙醚 、 溶剂黄146 为溶剂， 17.0 ℃ 、101.33 kPa 条件下， 反应 6.5h， 生成 (4as,8ar)-8a-methyloctahydronaphthalen-4a(2H)-ol
  参考文献：
  名称：

  8a-甲基-和8a-乙基-1,2,3,4,4a，7,8,8a-八氢萘基氢过氧化物的形成和烯丙基重排中的立体选择性

  摘要：

  对4a-甲基-和4a-乙基-1,2,3,4,4a，5,6,7-八氢萘进行了单线态氧氧合，并表征了形成的各种氢过氧化物。证据表明，25°C下8aβ-烷基-1,2,3,4,4a，7,8,8a-八氢萘-4aα-基氢过氧化物（I ; R = Me或Et）在氯仿中不可逆地重排。仅得到4aβ-烷基-2,3,4,4a，5,6,7,8,8-八氢萘-2α-氢过氧化物（II）。在相同条件下，相应的8aβ-烷基-1,2,3,4,4a，7,8,8a-八氢萘-4aβ-基氢过氧化物的重新排列要慢得多。[图形省略]

  DOI：

  10.1039/p29880001847

文献信息

• Sesquiterpenoids—IV
  作者：C.H. Heathcock、T.Ross Kelly

  DOI：10.1016/s0040-4020(01)92007-1

  日期：1968.1

  Treatment of unsaturated acid 1 with refluxing formic acid leads to an equilibrium mixture of lactones 2 and 3 in a ratio of 2:1. The stereostructure of γ-lactone 2 is secured by its synthesis from epoxy-ester 6, the stereochemistry of which is deduced from reactivity arguments. The structure of δ-lactone 3 was proven by correlation with the trans-9-methoxy-10-methyl decalin 29, of unambiguous stereo-chemistry

  用回流的甲酸处理不饱和酸1导致内酯2和3以2∶1的比例的平衡混合物。γ-内酯2的立体结构通过其由环氧酯6的合成来确保，其立体化学由反应性论证推导。通过与明确的立体化学的反式-9-甲氧基-10-甲基十氢化萘29相关联，证明了δ-内酯3的结构。讨论了这种“甲基迁移”途径向嗜碱菌的优点。
• Electroorganic chemistry. 140. Electroreductively promoted intra- and intermolecular couplings of ketones with nitriles.
  作者：Tatsuya Shono、Naoki Kise、Taku Fujimoto、Naoto Tominaga、Hiroshi Morita

  DOI：10.1021/jo00052a036

  日期：1992.12

  Electroreduction of gamma and delta-cyano ketones in i-PrOH with Sn cathode gave alpha-hydroxy ketones and their dehydroxylated ketones as the intramolecularly coupled products. Guaiazulene, (-)-valeranone, polyquinanes, dihydrojasmone, methyl dihydrojasmonate, and rosaprostol have been synthesized by utilizing this electroreductive intramolecular coupling of gamma and delta-cyano ketones in one of the key steps. Similarly, electroreduction of a mixture of ketone and nitrile gave the corresponding intermolecularly coupled product. The product obtained by the electroreductive intermolecular coupling of (+)-dihydrocarvone with acetonitrile has been found to be the precursor of an effective chiral ligand for the enantioselective addition of diethylzinc to aldehydes.
• Lanthanides in organic synthesis. 3. A general procedure for five- and six-membered ring annulation
  作者：Gary A. Molander、Jeffrey B. Etter

  DOI：10.1021/jo00360a025

  日期：1986.5
• Conversion of linear trienes into bicyclic boranes via hydroboration-isomerization and their carbonylation. A simple synthesis of angularly substituted bicyclic alcohols
  作者：Herbert Charles Brown、Eiichi Negishi

  DOI：10.1021/ja01033a037

  日期：1969.2
• Hydroboration. 70. The polycyclic hydroboration of acyclic and cyclic trienes with borane in tetrahydrofuran and triethylamine-borane. Reexamination of the stereochemistry of isomeric perhydro-9b-boraphenalenes
  作者：Herbert C. Brown、Eiichi Negishi、William C. Dickason

  DOI：10.1021/jo00204a020

  日期：1985.2