α-(2-propynyl)-3-cyclohexene-1-methanol | 59639-79-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: α-(2-propynyl)-3-cyclohexene-1-methanol
• 英文别名: 1-(cyclohex-3-en-1-yl)but-3-yn-1-ol；1-Cyclohex-3-en-1-ylbut-3-yn-1-ol
• CAS: 59639-79-1
• 化学式: C₁₀H₁₄O
• 分子量: 150.221
• InChiKey: VRVOYEWDJPDYGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  α-(2-propynyl)-3-cyclohexene-1-methanol 在 咪唑 、 4-二甲氨基吡啶 、 正丁基锂 、 偶氮二异丁腈 、 三甲基溴硅烷 、 氢氟酸 、 三正丁基氢锡 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 、 苯 为溶剂， 反应 0.58h， 生成 1-(3-hydroxy-2,3,3a,4,5,7a-hexahydro-1H-inden-1-yl)propan-2-one
  参考文献：
  名称：

  Approaches to bicyclic ring systems via 1,5 allylic abstraction cyclisation

  摘要：

  A new 1, 5 allylic abstraction, cyclisation sequence has been developed and applied to the synthesis of fused bicyclic systems. Initial studies directed towards the synthesis of the bicyclo[3.3.0] octane skeleton are described. vinyl bromide 4 was subjected to standard cyclisation conditions to give 5 as a single isomer. Further studies were directly related to the development of the rearrangement sequence: vinyl bromide 10 was subject to cyclisation conditions to give 12 in moderate yield. A significant improvement in the rate and efficiency of this type of conversion was achieved by introducing an electron withdrawing group on the acceptor alkene, thus compound 17 gives 18 in excellent yield.

  DOI：

  10.1016/s0040-4020(01)88361-7
• 作为产物：
  描述：

  3-溴丙炔 、 3-环己烯甲醛 在 magnesium 、 mercury dichloride 作用下， 以 乙醚 为溶剂， 生成 α-(2-propynyl)-3-cyclohexene-1-methanol
  参考文献：
  名称：

  无配体金纳米颗粒催化的温和条件下共轭异戊烯向呋喃的环化异构化

  摘要：

  负载在TiO 2（1 mol％）上的Au纳米颗粒在非常温和的条件下催化共轭异戊烯向呋喃的定量环异构化。通过加入乙酸（1当量）可加快反应速度，但该酸不像相应的Au（III）催化的转化反应那样参与原脱氧步骤。该方法是纯均相的，因此允许在几次运行中有效地回收和再利用催化剂。

  DOI：

  10.1021/acs.orglett.9b01869

文献信息

• Stereoselective Barbier-Type Allylations and Propargylations Mediated by CpTiCl₃
  作者：Josefa L. López-Martínez、Irene Torres-García、Ignacio Rodríguez-García、Manuel Muñoz-Dorado、Miriam Álvarez-Corral

  DOI：10.1021/acs.joc.8b02643

  日期：2019.1.18

  CpTiCl2, prepared in situ by manganese reduction of CpTiCl3, is an excellent new system for the Barbier-type allylation and propargylation of carbonyl compounds. It can be used in catalytic amounts when combined with Et3N·HBr/TMSBr, which acts as a regenerating system. The high regio- and stereoselectivity shown by this system makes it useful for prenylation and crotylation processes in the synthesis

  CpTiCl 2，由锰还原CpTiCl的原位制备3，是用于羰基化合物的巴比尔型烯丙基炔丙基和优异的新系统。与再生系统Et 3 N·HBr / TMSBr结合使用时，可以催化量使用。该系统显示的高区域选择性和立体选择性使其可用于天然产物合成中的异戊二烯化和丁二酰化过程。
• Cycloisomerization of Conjugated Allenones into Furans under Mild Conditions Catalyzed by Ligandless Au Nanoparticles
  作者：Leandros Zorba、Marios Kidonakis、Iakovos Saridakis、Manolis Stratakis

  DOI：10.1021/acs.orglett.9b01869

  日期：2019.7.19

  Au nanoparticles supported on TiO2 (1 mol %) catalyze the quantitative cycloisomerization of conjugated allenones into furans under very mild conditions. The reaction rate is accelerated by adding acetic acid (1 equiv), but the acid does not participate in the protodeauration step as in the corresponding Au(III)-catalyzed transformation. The process is purely heterogeneous, allowing thus the recycling

  负载在TiO 2（1 mol％）上的Au纳米颗粒在非常温和的条件下催化共轭异戊烯向呋喃的定量环异构化。通过加入乙酸（1当量）可加快反应速度，但该酸不像相应的Au（III）催化的转化反应那样参与原脱氧步骤。该方法是纯均相的，因此允许在几次运行中有效地回收和再利用催化剂。
• Approaches to bicyclic ring systems via 1,5 allylic abstraction cyclisation
  作者：A.D. Borthwick、S. Caddick、P.J. Parsons

  DOI：10.1016/s0040-4020(01)88361-7

  日期：1992.11

  A new 1, 5 allylic abstraction, cyclisation sequence has been developed and applied to the synthesis of fused bicyclic systems. Initial studies directed towards the synthesis of the bicyclo[3.3.0] octane skeleton are described. vinyl bromide 4 was subjected to standard cyclisation conditions to give 5 as a single isomer. Further studies were directly related to the development of the rearrangement sequence: vinyl bromide 10 was subject to cyclisation conditions to give 12 in moderate yield. A significant improvement in the rate and efficiency of this type of conversion was achieved by introducing an electron withdrawing group on the acceptor alkene, thus compound 17 gives 18 in excellent yield.