2-(1-cyclohexen-1-yl)propan-1-ol | 115998-86-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(1-cyclohexen-1-yl)propan-1-ol
• 英文别名: 2-(cyclohex-1-enyl)propan-1-ol；2-cyclohex-1-enyl-propan-1-ol；2-(Cyclohexen-1-yl)propan-1-ol
• CAS: 115998-86-2
• 化学式: C₉H₁₆O
• 分子量: 140.225
• InChiKey: HHCZERSSFOOAHP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 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-(1-cyclohexen-1-yl)propan-1-ol 在 thallium(III) nitrate 作用下， 以 正戊烷 为溶剂， 反应 48.0h， 以63%的产率得到4-methyl-2-oxaspiro[4,4]nonan-1-one
  参考文献：
  名称：

  Reaction of 3-Alkenols with Thallium Trinitrate: An Unexpected and Useful Ring Contraction

  摘要：

  The first thallium trinitrate (TTN) mediated ring contraction of cyclic homoallylic alcohols, using a 1:1 mixture of AcOH and H2O as solvent, is described. The reaction or two of these alcohols with excess of TTN in pentane gave alpha-spirocyclopentyl-gamma-butirolactones in reasonable yields.

  DOI：

  10.1080/00397910008087377
• 作为产物：
  描述：

  2-cyclohex-1-enyl-propionic acid 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以94%的产率得到2-(1-cyclohexen-1-yl)propan-1-ol
  参考文献：
  名称：

  Thallium Trinitrate Mediated Oxidation of 3-Alkenols:  Ring Contraction vs Cyclization

  摘要：

  The reaction of a series of six-membered ring 3-alkenols with thallium trinitrate (TTN) in three different experimental conditions was studied. Either cyclization products or ring contraction products were obtained, depending on the structure of the substrate as well as the nature of the solvent. The reaction of a seven-membered ring 3-alkenol with TTN led to the ring contraction product exclusively.

  DOI：

  10.1021/jo011178m

文献信息

• Dynamic Kinetic Resolution of β-Substituted α-Diketones via Asymmetric Transfer Hydrogenation
  作者：Ting Chen、Wenjun Liu、Wei Gu、Shengtong Niu、Shouang Lan、Zhifei Zhao、Fan Gong、Jinggong Liu、Shuang Yang、Andrej Emanuel Cotman、Jinshuai Song、Xinqiang Fang

  DOI：10.1021/jacs.2c11149

  日期：2023.1.11

  the highly regio- and enantioselective semihydrogenation of unsymmetrical α-diketones are two formidable challenges in the field of contemporary asymmetric (transfer) hydrogenation. In this work, we report the highly regio- and stereoselective asymmetric semi-transfer hydrogenation of unsymmetrical α-diketones through a unique DKR mode, which features the reduction of the carbonyl group distal from the

  开发创新的动态动力学拆分 (DKR) 模式和实现不对称 α-二酮的高度区域选择性和对映选择性半氢化是当代不对称（转移）氢化领域的两个艰巨挑战。在这项工作中，我们报告了通过独特的 DKR 模式对不对称 α-二酮进行高度区域选择性和立体选择性的不对称半转移氢化，该模式的特点是将远离不稳定立体中心的羰基还原，而近端羰基保持不变。此外，该协议还提供了各种富含 α-羟基-α′-C(sp 2)-官能团，代表已知技术中未提供的新产品类别。产品的效用已在一系列进一步的转化中得到证明，包括药物分子的快速合成。还进行了密度泛函理论计算和大量控制实验，以获得对高选择性半氢化的更多机理见解。
• Barluenga, Jose; Alvarez, Flora; Concellon, Jose M., Journal of Chemical Research, Miniprint, 1987, # 12, p. 3265 - 3285
  作者：Barluenga, Jose、Alvarez, Flora、Concellon, Jose M.、Yus, Miguel

  DOI：——

  日期：——
• Bicyclic β-Hydroxytetrahydrofurans as Precursors of Medium Ring Keto-Lactones
  作者：Helena M. C. Ferraz、Luiz S. Longo

  DOI：10.1021/jo0626109

  日期：2007.4.1

  The reaction of a series of cis-fused bicyclic beta-hydroxytetrahydrofurans with ruthenium tetraoxide, generated in situ from ruthenium trichloride and sodium periodate, afforded 9- and 10-membered keto-lactones in moderate to good yields, in a clean and straightforward fashion. The starting beta-hydroxyethers were obtained from the corresponding 3-alkenols by two alternative procedures, depending on their pattern of substitution: (a) epoxidation by dimethyldioxirane, followed by base-catalyzed cyclization of the resulting epoxyalcohol, and (b) thallium trinitrate-mediated cyclization of the 3-alkenols, a method already described by our group.
• BARLUENGA, JOSE;ALVAREZ, FLORA;CONCELLON, JOSE M.;YUS, MIGUEL, J. CHEM. RES. (S),(1987) N 12, C. 402-403
  作者：BARLUENGA, JOSE、ALVAREZ, FLORA、CONCELLON, JOSE M.、YUS, MIGUEL

  DOI：——

  日期：——
• Thallium Trinitrate Mediated Oxidation of 3-Alkenols:  Ring Contraction vs Cyclization
  作者：Helena M. C. Ferraz、Luiz S. Longo、Julio Zukerman-Schpector

  DOI：10.1021/jo011178m

  日期：2002.5.1

  The reaction of a series of six-membered ring 3-alkenols with thallium trinitrate (TTN) in three different experimental conditions was studied. Either cyclization products or ring contraction products were obtained, depending on the structure of the substrate as well as the nature of the solvent. The reaction of a seven-membered ring 3-alkenol with TTN led to the ring contraction product exclusively.