1-(2-hydroxy-1-methylethyl)cyclohexanol | 90676-81-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2-hydroxy-1-methylethyl)cyclohexanol
• 英文别名: 1-(1-Hydroxypropan-2-yl)cyclohexan-1-ol
• CAS: 90676-81-6
• 化学式: C₉H₁₈O₂
• 分子量: 158.241
• InChiKey: ZLBWQTSMWQXYGK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• 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：

  1-(2-hydroxy-1-methylethyl)cyclohexanol 在 potassium tert-butylate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 3-methyl-1-oxaspiro[3.5]nonane
  参考文献：
  名称：

  The stereoselective synthesis of oxetanes; exploration of a new, Mitsunobu-style procedure for the cyclisation of 1,3-diols

  摘要：

  一种2-甲基-3-[1-(芳基硫）环己基]丙烷-1,3-二醇1在甲苯中与三苯基膦、Ziram® 2和DEAD反应，产物为3-甲基-2-[1-(芳基硫）环己基]噁烯3，产率为85%。我们进行了机理研究，找到了最佳反应条件，并探索了该反应适用的底物范围。我们还包括了一项X射线研究的结果，该研究显示化合物33（醇1的氧化产物）是磺酮而非先前报告的亚磺酸盐。

  DOI：

  10.1039/b106851b
• 作为产物：
  描述：

  [2-(5-bromopentyl)-1,3-dithian-2-yl]-dimethyl-prop-2-enylsilane 在 偶氮二异丁腈 、 双氧水 、 三正丁基氢锡 、 碳酸氢钠 、 potassium hydrogencarbonate 、 [双(三氟乙酰氧基)碘]苯 作用下， 以 水 、 乙腈 为溶剂， 生成 1-(2-hydroxy-1-methylethyl)cyclohexanol
  参考文献：
  名称：

  通过酰基硅烷的串联自由基环化将基团从硅转移到碳

  摘要：

  具有连接到硅上的烯烃或炔烃官能团的酰基硅烷的串联自由基环化提供了环状甲硅烷基醚，其被氧化水解以得到二醇或酮醇。

  DOI：

  10.1016/0040-4039(96)01773-x

文献信息

• The study of intramolecular tandem radical cyclizations of acylsilanes with radicalphiles attached on silicon
  作者：Kuo-Hsiang Tang、Fang-Yu Liao、Yeun-Min Tsai

  DOI：10.1016/j.tet.2004.12.053

  日期：2005.2

  Radical cyclizations of acylsilanes with radicalphilic pendant introduced on silicon proceeded in a tandem fashion to give spiro products containing a cyclic silyl ether skeleton. Because the alkoxysilyl group can be replaced with a hydroxy group through oxidation, the spiro silyl ethers can be converted into diols. In the case with a radical intermediate carrying 2-oxa-3-sila-6-heptenyl skeleton,

  带有在硅上引入的具有自由基的侧基的酰基硅烷的自由基环化以串联方式进行，以得到含有环状甲硅烷基醚骨架的螺环产物。因为烷氧基甲硅烷基可以通过氧化被羟基取代，所以螺硅烷基醚可以转化为二醇。在与自由基中间输送2-氧杂-3-硅杂-6-庚烯基骨架的情况下，产品从1,7-衍生内环化反应以良好产率获得。
• Simple Analogs of the Antiarthritic Steroids¹
  作者：Domenick Papa、Helen F. Ginsberg、Frank J. Villani

  DOI：10.1021/ja01646a047

  日期：1954.9
• Indirect electrooxidation of alcohols by a double mediatory system with two redox couples of [R2N+:O]/R2NO.cntdot. and [Br.cntdot. or Br+]/Br- in an organic-aqueous two-phase solution
  作者：Tsutomu Inokuchi、Sigeaki Matsumoto、Sigeru Torii

  DOI：10.1021/jo00007a031

  日期：1991.3

  An indirect electrooxidation method for alcohol to aldehyde or ketone conversion has been developed. This method, applicable to chemoselective oxidation, employs two redox couples, consisting of 2,2,6,6-tetramethyl-piperidine-1-oxyl derivatives 6 and active bromine species. The former is required for the chemical process and recycled, whereas the latter is to be involved in the electrochemical process. Three chemical events play an important role in this system: (1) the formation of [Br or Br+] from bromide ion by discharge on the anode in an aqueous solution, (2) the reaction of N-oxyl compounds 6 with active bromine species to generate N-oxoammonium ion 7, and (3) the oxidation of alcohols with 7 in an organic phase. Optimum conditions were established as follows: an aqueous 25% NaBr solution buffered at pH 8.6 in a binary system, the use of 1-10 mol % of 4-(benzoyloxy)piperidine derivatives 6, and adjustment of an electric current at 10-100 mA/cm2. The successful applications of the present method to the oxidation of a variety of primary and secondary alcohols including 1,n-diols, giving the corresponding carbonyl compounds, have delineated its synthetic utility. The chemoselective oxidation of a primary hydroxy group in the presence of secondary one has been achieved with a high selectivity by the present procedure.
• A selective and efficient method for alcohol oxidations mediated by N-oxoammonium salts in combination with sodium bromite
  作者：Tsutomu Inokuchi、Sigeaki Matsumoto、Tokio Nishiyama、Sigeru Torii

  DOI：10.1021/jo00289a016

  日期：1990.1
• SUGITA, TOSHIO;NISHIO, NBUYUKI;ICHIKAWA, KATSUHIKO, BULL. CHEM. SOC. JAP., 1982, 55, N 5, 1677-1678
  作者：SUGITA, TOSHIO、NISHIO, NBUYUKI、ICHIKAWA, KATSUHIKO

  DOI：——

  日期：——