2,3,4,4a,5,6,7,8-octahydro-4a-methyl-2-naphthalenol | 26675-10-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4,4a,5,6,7,8-octahydro-4a-methyl-2-naphthalenol
• 英文别名: 4a-methyl-2,3,4,4a,5,6,7,8-octahydronaphthalen-2-ol；10-methyl-Δ¹⁽⁹⁾-octalin-2-ol；Opt.-inakt. 7-Hydroxy-4a-methyl-1.2.3.4.4a.5.6.7-octahydro-naphthalin；4a-Methyl-2,3,4,4a,5,6,7,8-octahydro-[2]naphthol；10-Methyl-Δ¹⁽⁹⁾-octalol-(2)；9-Methyl-Δ⁴-octalol-(3)；4a-methyl-3,4,5,6,7,8-hexahydro-2H-naphthalen-2-ol
• CAS: 26675-10-5
• 化学式: C₁₁H₁₈O
• 分子量: 166.263
• InChiKey: ZRALQUNYQUFRDO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 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：

  2,3,4,4a,5,6,7,8-octahydro-4a-methyl-2-naphthalenol 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 L-(+)-diisopropyl tartrate 、 pyridinium chlorochromate 作用下， 生成 4A-甲基-4,4a,5,6,7,8-六氢-3H-萘-2-酮
  参考文献：
  名称：

  Absolute configuration of 1,2-disubstituted trans-cyclodecenes based on chemical correlation with (+)-dimethyl (2R)-2-butyl-2-methyloctanedioate

  摘要：

  DOI：

  10.1021/ja00390a008
• 作为产物：
  描述：

  4A-甲基-4,4a,5,6,7,8-六氢-3H-萘-2-酮 在 potassium tri-sec-butyl-borohydride 作用下， 生成 2,3,4,4a,5,6,7,8-octahydro-4a-methyl-2-naphthalenol
  参考文献：
  名称：

  Lithium and potassium trialkylborohydrides. Reagents for direct reduction of .alpha.,.beta.-unsaturated carbonyl compounds to synthetically versatile enolate anions

  摘要：

  DOI：

  10.1021/jo00874a028

文献信息

• Resolution of allylic alcohols by cholesterol oxidase isolated from Rhodococcus erythropolis
  作者：Serge Dieth、Denis Tritsch、Jean-François Biellmann

  DOI：10.1016/0040-4039(95)00235-5

  日期：1995.3

  The oxidation of non-steroidal compounds by cholesterol oxidase isolated from Rhodococcus erythropolis is reported for the first time. It was regio-, stereo- and enantio-selective. The enzyme oxidized preferentially the 2-cyclohexenyl-1-alcohols whose configuration is (S) at the reaction center.

  首次报道了从红球红球菌中分离出的胆固醇氧化酶对非甾体化合物的氧化作用。它是区域，立体和对映体选择性的。该酶优选在反应中心氧化构型为（S）的2-环己烯基-1-醇。
• Use of radical ring opening for introduction of alkyl and substituted alkyl groups with stereochemical control: a synthetic application of cyclopropylcarbinyl radicals
  作者：Derrick L. J. Clive、Sylvain Daigneault

  DOI：10.1021/jo00012a009

  日期：1991.6

  Cyclopropylcarbinols 2a and 2b (see Scheme I), which are accessible by a number of routes, can be converted into the corresponding radicals 3a and 3b, respectively. These radicals undergo peripheral ring-opening of the cyclopropyl substructure to afford substituted cycloalkenes 4a and 4b. The whole sequence represents a general method for attaching alkyl, and substituted alkyl, groups to an existing cyclic structure, and it can often be carried out with predictable stereo- and regiochemical control. Reaction conditions for the ring-opening depend on the substitution pattern of the cyclopropane: where the non-bridgehead carbon of the cyclopropane carries a strongly electron-withdrawing group, the ring-opening can be done at the reflux temperature of benzene. However, in the absence of such electron-withdrawing groups, a low temperature is best used in order to suppress ring expansion. Various methods that accommodate these requirements are available for generating the radicals.
• Absolute configuration of 1,2-disubstituted trans-cyclodecenes based on chemical correlation with (+)-dimethyl (2R)-2-butyl-2-methyloctanedioate
  作者：James A. Marshall、Katherine E. Flynn

  DOI：10.1021/ja00390a008

  日期：1982.12
• Julia,S. et al., Bulletin de la Societe Chimique de France, 1962, p. 374 - 376
  作者：Julia,S. et al.

  DOI：——

  日期：——
• An Investigation of Anchimeric Assistance in Certain Homoallylic Alcohols
  作者：WILLIAM J. A. VANDENHEUVEL、EVERETT S. WALLIS

  DOI：10.1021/jo01051a027

  日期：1962.4