(E)-1-styrylcyclohexanol | 33493-90-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-1-styrylcyclohexanol
• 英文别名: 1-Styryl-cyclohexan-1-ol；1-[(E)-2-phenylethenyl]cyclohexan-1-ol
• CAS: 33493-90-2
• 化学式: C₁₄H₁₈O
• 分子量: 202.296
• InChiKey: VASYLTAMYIGPOM-FMIVXFBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  (E)-1-styrylcyclohexanol 在 硫酸 作用下， 以 四氢呋喃 为溶剂， 生成 (E)-(2-(cyclohex-1-en-1-yl)vinyl)benzene
  参考文献：
  名称：

  A Conformational Study of Two Jet-Cooled Conjugated Styryl Cyclohexenes

  摘要：

  The S-1 <-- S-0 resonance-enhanced ionization spectra are presented for two jet-cooled cyclohexene compounds, 2-(trans-beta-styryl)-1,3,3-trimethylcyclohexene and 1-(trans-beta-styryl)-cyclohexene, in which the cyclohexene ring is formally conjugated to a styryl group. In the trimethyl-substituted derivative, strong steric interactions between the cyclohexene ring and styryl group are present, similar to those found in the retinal system, which significantly influence the ground-state molecular conformation. Both of these styryl cyclohexenes exhibit spectra that are dominated by an intense origin transition, indicating little change in molecular geometry between the two electronic states. In 2-(trans-beta-styryl)-1,3,3-trimethylcyclohexene, two peaks at 34 441 and 34 452 cm(-1) are assigned as origin transitions of different molecular conformations on the basis of power saturation experiments. A relationship between the origin transition energy and the torsional angle of the cyclohexene ring is derived and then used to determine the ground-state equilibrium torsional geometry for both compounds. The two conformations of 2-(trans-beta-styryl)-1,3,3-trimethylcyclohexene are determined to have the cyclohexene ring tilted +/-73 degrees out of the plane of the conjugated styryl system while in 1-(trans-beta-styryl)cyclohexene the cyclohexene double bond is found to be 14-21 degrees from a planar, fully conjugated conformation.

  DOI：

  10.1021/j100066a008
• 作为产物：
  描述：

  2'-benzyl-2'-(phenylsulfinyl)spiro 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 以87%的产率得到(E)-1-styrylcyclohexanol
  参考文献：
  名称：

  通过α，β-环氧亚砜由羰基化合物合成环氧化物和烯丙醇的新方法

  摘要：

  在-100°C下用1当量的正丁基锂轻松处理由羰基化合物制得的α，β-环氧亚砜，可得到高收率的脱硫环氧化物。在-70℃下用过量的正丁基锂处理时，在α位具有芳基甲基的相似的α，β-环氧亚砜得到3-芳基烯丙基醇。

  DOI：

  10.1016/s0040-4039(00)84534-7

文献信息

• Silver-catalyzed decarboxylative C(sp²)–C(sp³) coupling reactions <i>via</i> a radical mechanism
  作者：Zhongxue Fang、Chenlong Wei、Jing Lin、Zhenhua Liu、Wei Wang、Chenshu Xu、Xuemin Wang、Yu Wang

  DOI：10.1039/c7ob02455j

  日期：——

  A silver catalyzed decarboxylative C(sp2)–C(sp3) coupling of vinylic carboxylic acids with alcohols, alkylbenzenes, cycloalkanes and cyclic ethers was developed by using DTBP as an oxidant. This reaction tolerates a wide range of substrates, and products are obtained in good to excellent yields. The reaction also shows good stereoselectivity, and only trans-isomers are obtained. In addition, a radical

  通过使用DTBP作为氧化剂，开发了乙烯基羧酸与醇，烷基苯，环烷烃和环醚的银催化脱羧C（sp 2）-C（sp 3）偶联反应。该反应可耐受多种底物，并且以良好至极好的产率获得产物。该反应还显示出良好的立体选择性，并且仅获得反式异构体。此外，自由基途径将参与促进这种脱羧的C（sp 2）–C（sp 3）偶联反应。
• Preparation of oxetanes by 4-endo trig electrophilic cyclisations of cinnamic alcohols
  作者：Sébastien Albert、Sylvie Robin、Gérard Rousseau

  DOI：10.1016/s0040-4039(01)00226-x

  日期：2001.3

  The reaction of substituted cinnamic alcohols with bis(sym-collidine)bromine(I) hexafluorophosphate was examined. In general no oxetane was obtained when a substituent was fixed on the carboncarbon double bond. However, oxetanes were formed in high yields when two substituents were present in α of the alcohol function.

  取代的肉桂醇与双反应（符号-collidine）溴（I）六氟磷酸盐进行了研究。通常，当取代基固定在碳碳双键上时，没有得到氧杂环丁烷。然而，当在醇官能团的α中存在两个取代基时，以高产率形成氧杂环丁烷。
• Stereospecific Desulfinylation of α,β-Epoxy Sulfoxides with Butyllithium. A New Synthesis of Epoxides and Allylic Alcohols from Carbonyl Compounds
  作者：Tsuyoshi Satoh、Youhei Kaneko、Koji Yamakawa

  DOI：10.1246/bcsj.59.2463

  日期：1986.8

  easily prepared from carbonyl compounds and 1-chloroalkyl phenyl sulfoxide, with 1 equivalent of butyllithium at low temperature gave epoxides in good yields. The similar α,β-epoxy sulfoxides having an arylmethyl group at the α-position gave 3-aryl-allylic alcohols upon treatment with excess butyllithium at −70 °C. These reactions offer a simple and useful approach to the synthesis of epoxides and 3-aryl-allylic

  α,β-环氧亚砜很容易由羰基化合物和 1-氯代烷基苯基亚砜制备，在低温下用 1 当量的丁基锂脱亚硫基得到环氧化物，产率很高。在-70℃下用过量丁基锂处理后，在α-位具有芳甲基的类似α,β-环氧亚砜得到3-芳基-烯丙醇。这些反应为从羰基化合物合成环氧化物和 3-芳基-烯丙醇提供了一种简单而有用的方法。
• N-Heterocyclic Carbene-Catalyzed Hydrosilylation of Styryl and Propargylic Alcohols with Dihydrosilanes
  作者：Qiwu Zhao、Dennis P. Curran、Max Malacria、Louis Fensterbank、Jean-Philippe Goddard、Emmanuel Lacôte

  DOI：10.1002/chem.201101822

  日期：2011.8.29

  Reducing alkenes to tears: Addition of structurally diverse N‐heterocyclic carbenes (NHCs) to silicon allows the reduction of propargylic and styryl alcohols through an organocatalyzed silylation/direct hydride transfer tandem reaction (see scheme). Catalytic turnover is enabled by the switch to and from hypervalent silicon. This provides a new synthetic application of NHC–main group element complexes

  减少烯烃的眼泪：在硅上添加结构多样的N杂环卡宾（NHC），可通过有机催化的甲硅烷基化/直接氢化物转移串联反应还原炔丙醇和苯乙烯醇（参见方案）。切换到高价硅可以实现催化转换。这为NHC-主族元素配合物提供了新的合成应用。
• Stereo-controlled <i>anti</i>-hydromagnesiation of aryl alkynes by magnesium hydrides
  作者：Bin Wang、Derek Yiren Ong、Yihang Li、Jia Hao Pang、Kohei Watanabe、Ryo Takita、Shunsuke Chiba

  DOI：10.1039/d0sc01773f

  日期：——

  anti-hydromagnesiation of aryl alkynes was established using 1 : 1 molar combination of sodium hydride (NaH) and magnesium iodide (MgI2) without the aid of any transition metal catalysts. The resulting alkenylmagnesium intermediates could be trapped with a series of electrophiles, thus providing facile accesses to stereochemically well-defined functionalized alkenes. Mechanistic studies by experimental

  在不借助任何过渡金属催化剂的情况下，使用氢化钠（NaH）和碘化镁（MgI 2）的1：1摩尔结合物建立了芳基炔烃抗氢放大的简明方案。所得的烯基镁中间体可以被一系列亲电试剂捕获，从而提供了对立体化学上定义明确的官能化烯烃的便捷通道。通过实验和理论方法进行的机理研究表明，从氢化镁（MgH 2）中添加极性氢化物是该过程的原因。