ethyl 4-hydroxy-2-methylcyclohex-2-enecarboxylate | 61203-59-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl 4-hydroxy-2-methylcyclohex-2-enecarboxylate
• 英文别名: 4-ethoxycarbonyl-3-methyl-2-cyclohexen-1-ol；4-carbetoxy-3-methyl-2-cyclohexen-1-ol；4-Carbethoxy-3-methyl-2-cyclohexanol；4-Carbethoxy-3-methyl-2-cyclohexenol；Ethyl 4-hydroxy-2-methyl-2-cyclohexene-1-carboxylate；ethyl 4-hydroxy-2-methylcyclohex-2-ene-1-carboxylate
• CAS: 61203-59-6；61203-60-9；79057-41-3；79057-42-4；147255-19-4；147255-20-7；55972-84-4
• 化学式: C₁₀H₁₆O₃
• 分子量: 184.235
• InChiKey: ZCSQROHNFGOIGE-UHFFFAOYSA-N

物化性质

• 沸点：
  268.8±40.0 °C(Predicted)
• 密度：
  1.091±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 4-hydroxy-2-methylcyclohex-2-enecarboxylate 、 甲乙酐 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 0.83h， 以91%的产率得到4-ethoxycarbonyl-3-methyl-2-cyclohexen-1-ol formate
  参考文献：
  名称：

  Chemoselective Removal of Allylic Formyloxy Group Using Sml₂

  摘要：

  A variety of allylic formates are chemoselectively transformed into the corresponding olefins in excellent yields on treatment with Sml2 in THF-HMPA-H2O (20:5:1), even though allylic acetate and allylic ether groups are present in the same molecule.

  DOI：

  10.1080/00397919508011375
• 作为产物：
  描述：

  2-甲基-4-羰基-2-环己烯-1-羧酸乙酯 在 sodium tetrahydroborate 、 calcium(II) trifluoromethanesulfonate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.5h， 以52%的产率得到ethyl 4-hydroxy-2-methylcyclohex-2-enecarboxylate
  参考文献：
  名称：

  有机合成中的镧系元素置换：α，β-不饱和的Luche型还原 酮类 在三氟甲磺酸钙存在下

  摘要：

  钙介导的区域选择性1,2-还原具有挑战性的α，β-不饱和键的发展 酮类据报道，例如2-环戊烯酮。对应的盟友酒类使用Ca（OTf）2和NaBH 4具有很好的区域选择性。此外，我们已经表明，我们的方法可以立体选择性地还原叠氮基酮类。

  DOI：

  10.1039/c2gc35619h

文献信息

• Highly regio- and stereoselective reductions of carbonyl compounds in aqueous glycosidic media
  作者：Cécile Denis、Benoît Laignel、Daniel Plusquellec、Jean-Yves Le Marouille、Alain Botrel

  DOI：10.1016/0040-4039(95)02094-2

  日期：1996.1

  Highly regioselective reductions of α,β-unsaturated ketones to the corresponding allylic alcohols were performed in essentially quantitative yields in aqueous media containing either glycosidic surfactants or amphiphilic carbohydrates. Reductions of cyclohexanones and cyclohexenones lead under the same conditions, stereoselectively to reduced compounds bearing an equatorial alcohol function. Hydrophobic

  在含有糖苷型表面活性剂或两亲性碳水化合物的水性介质中，以基本上定量的产率将α，β-不饱和酮高度区域选择性地还原为相应的烯丙基醇。环己酮和环己酮的还原反应在相同条件下进行，立体选择性地还原了具有赤道醇功能的化合物。两亲性碳水化合物和亲脂性底物之间的疏水相互作用被建模，并应考虑到观察到的立体分化。
• Silica gel-supported zinc borohydride. 2. Regioselective 1,2-reduction of conjugated ketones and aldehydes to the corresponding allylic alcohols
  作者：Brindaban C. Ranu、Asish R. Das

  DOI：10.1021/jo00015a042

  日期：1991.7
• Lanthanoids in organic synthesis. 6. Reduction of .alpha.-enones by sodium borohydride in the presence of lanthanoid chlorides: synthetic and mechanistic aspects
  作者：Andre L. Gemal、Jean Louis Luche

  DOI：10.1021/ja00408a029

  日期：1981.9
• Aminoborohydrides. 4. The Synthesis and Characterization of Lithium Aminoborohydrides: A New Class of Powerful, Selective, Air-Stable Reducing Agents
  作者：Gary B. Fisher、Joseph C. Fuller、John Harrison、Salvador G. Alvarez、Elizabeth R. Burkhardt、Christian T. Goralski、Bakthan Singaram

  DOI：10.1021/jo00100a046

  日期：1994.10

  Lithium aminoborohydrides (LiABH(3)) are a new class of powerful yet selective reducing agents that reproduce, in air, virtually all of the transformations for which lithium aluminum hydride is now used. LiABH(3)'s can be readily prepared as solids or generated in situ, are nonpyrophoric, and liberate hydrogen only slowly with protic solvents above pH 4. LiABH(3)'s can be handled in dry air as easily as sodium borohydride and retain their chemical activity for at least 6 months when stored under nitrogen or dry air at 25 degrees C. LiABH(3)'s can be synthesized from any primary or secondary amine, thus allowing control of the steric and electronic environment of these reagents.
• A Simple, Efficient, and Selective Method for Tetrahydropyranylation of Alcohols on a Solid Phase of Alumina Impregnated with Zinc Chloride
  作者：Brindaban C. Ranu、Manika Saha

  DOI：10.1021/jo00105a054

  日期：1994.12