1-(环己-3-烯基)丙-2-烯-1-醇 | 104550-66-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-(环己-3-烯基)丙-2-烯-1-醇
• 英文名称: 1-(cyclohex-3-en-1-yl)prop-2-en-1-ol
• 英文别名: 1-cyclohex-3-en-1-ylprop-2-en-1-ol
• CAS: 104550-66-5
• 化学式: C₉H₁₄O
• 分子量: 138.21
• InChiKey: IPKJWMLMLWWINZ-UHFFFAOYSA-N

物化性质

• 沸点：
  89-91 °C(Press: 6 Torr)
• 密度：
  0.9591 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 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-(环己-3-烯基)丙-2-烯-1-醇 在 Lindlar's catalyst 、 钯 potassium hydrogensulfate 、 氢气 作用下， 以 甲醇 为溶剂， 生成 正丙基环己烷
  参考文献：
  名称：

  Kugatova,G.P. et al., Journal of general chemistry of the USSR, 1961, vol. 31, p. 556 - 561

  摘要：

  DOI：
• 作为产物：
  描述：

  1-环己-3-烯基-丙-2-炔-1-醇 在 Lindlar's catalyst 氢气 作用下， 生成 1-(环己-3-烯基)丙-2-烯-1-醇
  参考文献：
  名称：

  Kugatova,G.P. et al., Doklady Chemistry, 1960, vol. 133, p. 789 - 791

  摘要：

  DOI：

文献信息

• Stereoselective Dehydroxyboration of Allylic Alcohols to Access (<i>E</i>)-Allylboronates by a Combination of C–OH Cleavage and Boron Transfer under Iron Catalysis
  作者：Wei Su、Ting-Ting Wang、Xia Tian、Jian-Rong Han、Xiao-Li Zhen、Shi-Ming Fan、Ya-Xin You、Yu-Kun Zhang、Rui-Xiao Qiao、Qiushi Cheng、Shouxin Liu

  DOI：10.1021/acs.orglett.1c03359

  日期：2021.12.3

  Iron-catalyzed direct SN2′ dehydroxyboration of allylic alcohols has been developed to access (E)-stereoselective allylboronates. Allylic alcohols with diverse structures and functional groups, especially derived from natural products, underwent smooth transformation. The six-membered ring transition state formed by allylic alcohols and iron–boron intermediate was indicated to be the key component

  铁催化的烯丙醇直接 S N 2' 脱羟基硼酸已被开发用于获得 ( E )-立体选择性烯丙基硼酸酯。具有多种结构和官能团的烯丙醇，特别是来自天然产物的烯丙醇，经历了平稳的转变。由烯丙醇和铁-硼中间体形成的六元环过渡态被证明是参与硼基团转移、C-OH键活化和立体选择性控制的关键成分。
• Iridium(I)-Catalyzed Stereospecific Decarboxylative Allylic Amidation of Chiral Branched Benzyl Allyl Imidodicarboxylates
  作者：Om V. Singh、Hyunsoo Han

  DOI：10.1021/ol702115h

  日期：2007.11.1

  Ir(I)-catalyzed decarboxylative allylic amidation of chiral branched benzyl allyl imidodicarboxylates has been shown to proceed with complete retention of enantiomeric purity and configuration. The transformation is stereospecific and appears to be quite general, accommodating a wide range of R groups.

  已显示手性支化的苄基烯丙基亚氨基二羧酸二甲酯的Ir（I）催化的脱羧烯丙基酰胺化反应可完全保留对映体的纯度和构型。该转化是立体特异性的，并且看起来是相当普遍的，可容纳各种各样的R基团。
• Aerobic Oxidative Coupling between Carbon Nucleophiles and Allylic Alcohols: A Strategy to Construct β-(Hetero)Aryl Ketones and Aldehydes through Hydrogen Migration
  作者：Liangbin Huang、Ji Qi、Xia Wu、Wanqing Wu、Huanfeng Jiang

  DOI：10.1002/chem.201302962

  日期：2013.11.11

  reaction: A highly efficient PdII‐catalyzed intermolecular oxidative‐coupling reaction is reported, inspired by the fundamental Heck and Wacker processes. The (hetero)aryl‐PdX species, originating from CH activation step or desulfonyl hydrazides, coupled with allylic alcohols by using oxygen as the sole oxidant (see scheme).

  Wacker的反应：受基本的Heck和Wacker过程的启发，据报道有一种高效的Pd II催化的分子间氧化偶联反应。（杂）芳基- PDX物种，选自C始发 ħ活化步骤或desulfonyl酰肼，通过使用氧作为唯一的氧化剂（参见方案）加上烯丙基醇。
• Ruthenium- and rhodium-catalyzed oxidative alkylation of C–H bonds: efficient access to β-aryl ketones
  作者：Ji Qi、Liangbin Huang、Zhaoyang Wang、Huanfeng Jiang

  DOI：10.1039/c3ob41590b

  日期：——

  Ruthenium- and rhodium-catalyzed oxidative couplings between versatile directed aromatic C–H bonds and allylic alcohols have been achieved. This method provides efficient synthesis of functional β-aryl ketones and aldehydes in good to excellent yields, and the carbonyl group in the desired products was a significant synthon for organic synthesis.

  通用的定向芳族碳氢键与烯丙基醇之间已实现了钌和铑催化的氧化偶联。该方法以良好至优异的产率提供了功能性β-芳基酮和醛的有效合成，并且所需产物中的羰基是有机合成的重要合成子。
• Synthesis of <i>β</i> ‐Isoxazole Carbonyl Derivatives and their Analogues <i>via</i> Palladium‐Catalyzed Sequential C( <i>sp</i> ² )−O/C( <i>sp</i> ² )−C( <i>sp</i> ³ ) Bond Formations
  作者：Wanqing Wu、Can Li、Fei Zhou、Jianxiao Li、Xiaoqing Xu、Huanfeng Jiang

  DOI：10.1002/adsc.201900391

  日期：2019.8.21

  An efficient Pd(II)‐catalyzed one‐pot tandem cyclization/alkylation reaction of internal alkynes has been reported. In this reaction, a wide range of structurally diverse β/;‐isoxazole aldehydes/ketones could be obtained in good to excellent yields from various alkynyl oxime ethers and allylic or homoallylic alcohols. The gram‐scale experiment and various transformations of the newly obtained products

  已经报道了有效的Pd（II）催化内部炔烃的一锅串联串联环化/烷基化反应。在该反应中，可以从各种炔基肟醚和烯丙基或均烯丙基醇以良好或优异的收率获得各种结构多样的β /;-异恶唑醛/酮。克级实验和对新获得产品的各种转化表明，该方法应该是一种通用且有用的合成工具。