1-(1-cyclohexenyl)-3-buten-1-ol | 93743-28-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(1-cyclohexenyl)-3-buten-1-ol
• 英文别名: 1-(cyclohexen-1-yl)-3-buten-1-ol；1-cyclohex-1-enyl-but-3-en-1-ol；1-Cyclohexenyl-3-buten-1-ol；1-(cyclohexen-1-yl)but-3-en-1-ol
• CAS: 93743-28-3
• 化学式: C₁₀H₁₆O
• 分子量: 152.236
• InChiKey: ZEYVUBUCMZCWIN-UHFFFAOYSA-N

物化性质

• 沸点：
  83-86 °C(Press: 2.5 Torr)
• 密度：
  0.957±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  11
• 可旋转键数：
  3
• 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：

  1-(1-cyclohexenyl)-3-buten-1-ol 、 氢化钾 以69%的产率得到
  参考文献：
  名称：

  TSUJI, JIRO;SHIMIZU, ISAO;KOBAYASHI, YUICHI, ISRAEL J. CHEM., 1984, 24, N 2, 153-156

  摘要：

  DOI：
• 作为产物：
  描述：

  乙酸烯丙酯 、 1-cyclohexene-1-carboxaldehyde 在 rhodium(III) chloride hydrate 、 一氧化碳 、 水 、 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 70.0~80.0 ℃ 、206.85 kPa 条件下， 以78%的产率得到1-(1-cyclohexenyl)-3-buten-1-ol
  参考文献：
  名称：

  水煤气变换反应驱动的催化亲核烯丙基化

  摘要：

  钌与烯丙基亲核试剂的醛催化烯丙基化已被证明是在温和条件下形成碳-碳键的有效方法。此反应从最初的偶然发现到其一般合成范围的演变过程都进行了详细介绍，突出了水，一氧化碳和胺在更完整的催化循环生成中的作用。结果表明，使用不对称的烯丙基亲核亲核试剂可以通过调节反应条件来优先形成产物。（E）-肉桂酸乙酸酯和乙烯基环氧乙烷均有效地用于形成抗支链产物（抗/ syn最高> 20：1 ）和E-线性产物（最高> 20：1 E / s ）Z）分别与芳香族，α，β-不饱和和脂肪族醛形成高选择性。强调了使反应对映选择性的尝试，包括对苯甲醛高达75:25的对映富集。

  DOI：

  10.1021/acs.joc.7b02658

文献信息

• Pd-catalyzed nucleophilic allylic alkylation of aliphatic aldehydes by the use of allyl alcohols
  作者：Masanari Kimura、Masamichi Shimizu、Shuji Tanaka、Yoshinao Tamaru

  DOI：10.1016/j.tet.2005.02.005

  日期：2005.4

  Under catalysis of Pd(OAc)2-(P-n-Bu)3, Et2Zn promotes a variety of allyl alcohols to undergo nucleophilic allylation of aliphatic aldehydes and ketones at room temperature and provides homoallyl alcohols in 60–90 and ca. 60% isolated yield, respectively. The reaction is irreversible and kinetically controlled, and unique regio- and stereoselectivities observed for the allylation with unsymmetrically

  在Pd（OAc）2-（P- n- Bu）3的催化下，Et 2 Zn促进各种烯丙醇在室温下经历脂肪族醛和酮的亲核烯丙基化反应，并在60-90和90内提供均烯丙基醇。分离产率分别为60％。该反应是不可逆的并且是动力学控制的，并且讨论了用不对称取代的烯丙醇进行烯丙基化时观察到的独特的区域选择性和立体选择性。
• Method for Forming Allylic Alcohols
  申请人：Denmark Scott E.

  公开号：US20140031562A1

  公开（公告）日：2014-01-30

  A method of performing a chemical reaction includes reacting an allyl donor and a substrate in a reaction mixture, and forming a homoallylic alcohol in the reaction mixture. The substrate may be an aldehyde or a hemiacetal. The reaction mixture includes a ruthenium catalyst, carbon monoxide at a level of at least 1 equivalent relative to the substrate, and water at a level of at least 1 equivalent relative to the substrate, and an amine at a level of from 0 to 0.5 equivalent relative to the substrate. The reaction mixture may also include a halide, and the equivalents of the amine may be similar to those of the halide. The reacting includes maintaining the reaction mixture at a temperature of at least 40° C. The method may be catalytic in metal, environmentally benign, amenable to large-scale applications, and applicable to a wide range of substrates.

  一种进行化学反应的方法包括在反应混合物中反应烯丙基供体和底物，并在反应混合物中形成同烯丙基醇。底物可以是醛或半缩醛。反应混合物包括一种钌催化剂，一定量的一氧化碳（相对于底物至少1当量），一定量的水（相对于底物至少1当量）和一定量的胺（相对于底物从0到0.5当量）。反应混合物还可以包括卤化物，胺的当量可以与卤化物的当量类似。反应包括将反应混合物保持在至少40°C的温度下。该方法可能是金属催化的，对环境友好，适用于大规模应用，并适用于广泛的底物范围。
• Catalytic, Nucleophilic Allylation of Aldehydes with Allyl Acetate
  作者：Scott E. Denmark、Son T. Nguyen

  DOI：10.1021/ol8028725

  日期：2009.2.5

  A new catalytic allylation of aldehydes has been developed that employs allyl acetate as the allylating reagent. Under catalysis by ruthenium trichloride (3 mol %) in the presence of carbon monoxide (30 psi), water (1.5 equiv), and triethylamine (0.1 equiv), a wide range of aromatic, olefinic, and aliphatic aldehydes are efficiently allylated under mild conditions (70 degrees C, 24-48 h). The stoichiometric byproducts of this reaction are carbon dioxide and acetic acid.
• Nasarow; Sarezkaja, Zhurnal Obshchei Khimii, 1957, vol. 27, p. 624,633
  作者：Nasarow、Sarezkaja

  DOI：——

  日期：——
• [EN] METHOD FOR FORMING ALLYLIC ALCOHOLS<br/>[FR] PROCÉDÉ DE FORMATION D'ALCOOLS ALLYLIQUES
  申请人：UNIV ILLINOIS

  公开号：WO2010025366A2

  公开（公告）日：2010-03-04

  A method of performing a chemical reaction includes reacting an allyl donor and a substrate in a reaction mixture, and forming a homoallylic alcohol in the reaction mixture. The substrate may be an aldehyde or a hemiacetal. The reaction mixture includes a ruthenium catalyst, carbon monoxide at a level of at least 1 equivalent relative to the substrate, and water at a level of at least 1 equivalent relative to the substrate, and an amine at a level of from 0 to 0.5 equivalent relative to the substrate. The reaction mixture may also include a halide, and the equivalents of the amine may be similar to those of the halide. The reacting includes maintaining the reaction mixture at a temperature of at least 40°C. The method may be catalytic in metal, environmentally benign, amenable to large-scale applications, and applicable to a wide range of substrates.