2-(cyclohexylidenemethyl)tetrahydro-2H-pyran | 1010081-67-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 2-(cyclohexylidenemethyl)tetrahydro-2H-pyran
• 英文别名: 2-(Cyclohexylidenemethyl)oxane；2-(cyclohexylidenemethyl)oxane
• CAS: 1010081-67-0
• 化学式: C₁₂H₂₀O
• 分子量: 180.29
• InChiKey: FFFWICQQZFRXIW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(cyclohexylidenemethyl)tetrahydro-2H-pyran 在 iron p-toluenesulfonate 作用下， 以 1,2-二氯乙烷 为溶剂， 以67%的产率得到2-(cyclohex-1-en-1-ylmethyl)tetrahydro-2H-pyran
  参考文献：
  名称：

  Chemoselective Activities of Fe(III) Catalysts in the Hydrofunctionalization of Allenes

  摘要：

  A range of tetrahydropyrans and piperidines were produced by Fe(III)-catalyzed intramolecular hydroalkoxylation and hydroamination reactions of allenes. Various Fe catalysts with different counterions were tested. Their activities toward allene and alkene activation depended sensitively on their counterion and reaction conditions. Mechanistic study of the reaction intermediates found a new reaction pattern involving the Fe catalysts and diene substrates.

  DOI：

  10.1021/ol303021d
• 作为产物：
  描述：

  (E)-1-(6-hydroxyhex-1-enyl)-cyclohexanol 在 三苯基膦氯金 4 A molecular sieve 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以91%的产率得到2-(cyclohexylidenemethyl)tetrahydro-2H-pyran
  参考文献：
  名称：

  Au-Catalyzed Cyclization of Monoallylic Diols

  摘要：

  The Ph3PAuCl/AgOTf-catalyzed cyclization of monoallylic diols to form tetrahydropyrans is reported. The reactions proceed rapidly at temperatures as low as -78 degrees C with catalyst loadings as low as 0.1 mol % to provide the products in 79-99% yield. A broad range of structurally diverse substrates perform well in the reaction. When 2,6-disubstituted tetrahydropyrans are produced, the reaction is highly diastereoselective for the 2,6-cis product.

  DOI：

  10.1021/ol703002p

文献信息

• Aerobic Allylation of Alcohols with Non-Activated Alkenes Enabled by Light-Driven Selenium-π-Acid Catalysis
  作者：Alexander Breder、Katharina Rode、Martina Palomba、Stefan Ortgies、Rene Rieger

  DOI：10.1055/s-0037-1609938

  日期：2018.10

  acyclic ethers is accessed with very high functional group tolerance and excellent regioselectivity. A new organocatalytic protocol for the aerobic dehydrogenative allylation of alcohols using non-activated alkenes as the allylating reagent and ambient air as the terminal oxidant is established. Mechanistically, the procedure relies on the interplay of a diselane and a photo­redox catalyst by means of

  摘要 建立了一种新的有机催化方案，用于使用非活化烯烃作为烯丙基化试剂和环境空气作为末端氧化剂对酒精进行好氧脱氢烯丙基化。从机械上讲，该程序依赖于二癸烷和光氧化还原催化剂通过光诱导的电子转移过程的相互作用。在优化的条件下，可以获得非常高的官能团耐受性和出色的区域选择性的各种环状和无环醚。 建立了一种新的有机催化方案，用于使用非活化烯烃作为烯丙基化试剂和环境空气作为末端氧化剂对酒精进行好氧脱氢烯丙基化。从机械上讲，该程序依赖于二癸烷和光氧化还原催化剂通过光诱导的电子转移过程的相互作用。在优化的条件下，可以获得非常高的官能团耐受性和出色的区域选择性的各种环状和无环醚。
• Au-Catalyzed Cyclization of Monoallylic Diols
  作者：Aaron Aponick、Chuan-Ying Li、Berenger Biannic

  DOI：10.1021/ol703002p

  日期：2008.2.1

  The Ph3PAuCl/AgOTf-catalyzed cyclization of monoallylic diols to form tetrahydropyrans is reported. The reactions proceed rapidly at temperatures as low as -78 degrees C with catalyst loadings as low as 0.1 mol % to provide the products in 79-99% yield. A broad range of structurally diverse substrates perform well in the reaction. When 2,6-disubstituted tetrahydropyrans are produced, the reaction is highly diastereoselective for the 2,6-cis product.
• Chemoselective Activities of Fe(III) Catalysts in the Hydrofunctionalization of Allenes
  作者：Min Seok Jung、Won Sun Kim、Ye Ho Shin、Ha Jeong Jin、Young Sam Kim、Eun Joo Kang

  DOI：10.1021/ol303021d

  日期：2012.12.21

  A range of tetrahydropyrans and piperidines were produced by Fe(III)-catalyzed intramolecular hydroalkoxylation and hydroamination reactions of allenes. Various Fe catalysts with different counterions were tested. Their activities toward allene and alkene activation depended sensitively on their counterion and reaction conditions. Mechanistic study of the reaction intermediates found a new reaction pattern involving the Fe catalysts and diene substrates.