1-甲基环己-3-烯-1-醇 | 33061-16-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-甲基环己-3-烯-1-醇
• 英文名称: 3-methyl-3-cyclohexenol
• 英文别名: 1-methylcyclohex-3-en-1-ol；1-Methyl-3-cyclohexenol；4-Hydroxi-4-methyl-cyclohexen；1-Methyl-3-cyclohexen-1-OL
• CAS: 33061-16-4
• 化学式: C₇H₁₂O
• 分子量: 112.172
• InChiKey: TYTCCHDSBUCLPV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 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：

  1-甲基环己-3-烯-1-醇 以30%的产率得到
  参考文献：
  名称：

  RAMALAH, F.;RAO, A. S., TETRAHEDRON LETT., 29,(1987) N 17, 2119-2120

  摘要：

  DOI：
• 作为产物：
  描述：

  1-methyl-7-oxa-bicyclo[4.1.0]hept-3-ene 生成 1-甲基环己-3-烯-1-醇
  参考文献：
  名称：

  Conformational aspects of the directive effect of the homoallylic hydroxyl group in the Simmons-Smith reaction

  摘要：

  DOI：

  10.1021/jo00970a015

文献信息

• Reductive Radical Annulation Strategy toward Bicyclo[3.2.1]octanes: Synthesis of <i>ent</i>-Kaurane and Beyerane Diterpenoids
  作者：Junming Zhuo、Chunlin Zhu、Jinbao Wu、Zijian Li、Chao Li

  DOI：10.1021/jacs.1c11623

  日期：2022.1.12

  Here we report a general [3 + 2] radical annulation that allows the facile construction of bicyclo[3.2.1]octane motifs in ent-kaurane- and beyerane-type diterpenoids. This radical annulation is difficult to control but was realized by harnessing an unprecedented and counterintuitive effect of TEMPO. Eleven natural products with a wide array of oxidation states are easily prepared, demonstrating the

  在这里，我们报告了一个通用的 [3 + 2] 自由基环化，它允许在ent -kaurane- 和 beyerane 型二萜中轻松构建双环 [3.2.1] 辛烷基序。这种激进的环化很难控制，但通过利用 TEMPO 前所未有的和违反直觉的效果来实现。11 种具有多种氧化态的天然产物很容易制备，证明了这种简单合成策略的强大效用。
• Mechanism of the 1,3-Sigmatropic Shift of 2-Vinylcyclobutanol Alkoxides
  作者：Nathan J. Harris、Joseph J. Gajewski

  DOI：10.1021/ja00093a009

  日期：1994.7

  The rate of rearrangement of 2-vinylcyclobutanol was studied in dimethyl sulfoxide and tetrahydrofuran solvents. Rearrangement to 3-cyclohexenol in 1% aqueous DMSO is catalyzed by lithium hydroxide. When lithium bromide is added to this medium, the rate is diminished by a factor of 17, due to the effect of added lithium cation on the ion-pairing equilibrium. Disappearance of the potassium salt (E isomer) in THF at -22 degrees C shows first-order behavior over four half-lives, but the first-order rate constant varies inversely with starting alkoxide concentration, suggesting that an ion pair dissociation equilibrium precedes rearrangement. The rearrangement of the potassium salt in 10:1 THF/HMPA is accelerated ii-fold over the rate in pure THF, due to specific solvation of the cation by HMPA. At 2 degrees C in THF the sodium salt of (Z)-2-vinylcyclobutanol epimerizes to the E isomer at a rate 36-fold faster than the E alkoxide rearranges to the product. The potassium (E)-2-(2-propenyl)cyclobutoxide salt rearranges 17 times slower than potassium 2-vinylcyclobutoxide, in agreement with a previous comparison of rates of fragmentations of homoallylic alkoxides. Secondary deuterium kinetic isotope effect (kie) measurements were made by rearranging mixtures of deuterated and nondeuterated potassium vinylcyclobutoxides at 0 degrees C in diethyl ether and analyzing the extent of reaction by GC and the isotopic content of the mixture by proton NMR. The large normal kie (k(H)/k(D2) = 1.34 +/- 0.04) at the terminal vinyl positions and the small normal kie at the carbinol position (k(H)/k(D) = 1.12 +/- 0.06) are explainable if an allyl anion/aldehyde intermediate species is formed. Ab initio calculations suggest that such an intermediate can exist in several possible conformations and should be nearly as stable in the gas phase as the starting vinylcyclobutoxide.
• Synthesis of Z-allylic acetates via fragmentation of cyclic homoallylic alcohols
  作者：P Ramaiah、A.S Rao

  DOI：10.1016/s0040-4039(00)87850-8

  日期：——
• Hydroxylation of Alkenes with Ozone on Silica Gel
  作者：Ehud KEINAN、Yehuda MAZUR

  DOI：10.1055/s-1976-24104

  日期：——
• RAMALAH, F.;RAO, A. S., TETRAHEDRON LETT., 29,(1987) N 17, 2119-2120
  作者：RAMALAH, F.、RAO, A. S.

  DOI：——

  日期：——