2-hexyl-1-phenyl-3-buten-1-ol | 63922-86-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-hexyl-1-phenyl-3-buten-1-ol
• 英文别名: 2-ethenyl-1-phenyloctan-1-ol
• CAS: 63922-86-1
• 化学式: C₁₆H₂₄O
• 分子量: 232.366
• InChiKey: YWMSYNSYSYNBRH-UHFFFAOYSA-N

物化性质

• 沸点：
  337.4±11.0 °C(Predicted)
• 密度：
  0.936±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1,2-壬二烯 、 苯甲醛 在 dichloroalane 、 苯硼酸 作用下， 生成 2-hexyl-1-phenyl-3-buten-1-ol
  参考文献：
  名称：

  艾伦烯的区域选择性氢铝化及其合成应用

  摘要：

  使用 [TiCl2(Cp)2]、TiCl4、TiCl3、ZrCl4 和 [ZrCl2(Cp)2] 催化剂在 THF 中用 LiAlH4 对末端丙二烯、1,2-壬二烯进行加氢铝化，通过淬灭提供了多种氘化物质用 D2O 加氢铝化产物，而 PhB(OH)2 催化加氢铝化用 AlHCl2 在乙醚中以高产率得到>95% 纯度的 1-壬烯-3-d 作为主要产物 (92%)。使用PhB(OH) 2 催化的氢铝化产物使苯甲醛烯丙基化表明所得的氢铝化产物可能是烯丙基铝化合物，2-壬烯基二氯化铝。使用这种烯丙基铝化合物进行反式肉桂醛的烯丙基化反应具有高区域选择性，酮官能团保持完整。环氧化物的烯丙基化开环反应的区域选择性较小。

  DOI：

  10.1246/bcsj.66.3783

文献信息

• Regioselective reaction of allylbenzotriazoles with aldehydes and ketones in the presence of lithium
  作者：Alan R. Katritzky、Clara N. Fali、Ming Qi

  DOI：10.1016/s0040-4039(97)10601-3

  日期：1998.1

  The reactions of α- and γ-substituted allylbenzotriazoles 2, 3 and 4 with an excess of lithium in THF at −78 °C generate various allyllithiums, which react readily with aldehydes and ketones with high regioselectivity to give predominantly the branched products 5 in excellent yields.

  α和γ取代的烯丙基苯并三唑2、3和4与过量锂在THF中在-78°C的反应生成各种烯丙基锂，这些烯丙基锂易于与醛和酮反应，并具有较高的区域选择性，从而以优异的纯度得到主要的支链产物5产量。
• Synthesis of Pinacol Allylic Boronic Esters via Olefin Cross-Metathesis between Pinacol Allylboronate and Terminal or Internal Alkenes
  作者：Yasunori Yamamoto、Miki Takahashi、Norio Miyaura

  DOI：10.1055/s-2002-19356

  日期：——

  The ruthenium-catalyzed olefin cross-metathesis between pinacol allylboronate, CH2=CHCH2B(O2C2Me4), and RCH=CH2 giving RCH=CHCH2B(O2C2Me4) was carried out in refluxing CH2Cl2 in the presence of an alkylidene-ruthenium complex (3 mol%).

  频哪醇烯丙基硼酸酯、CH2=CH B(O2C2Me4) 和 RCH= 之间的钌催化烯烃交叉复分解反应在亚烷基-钌络合物 (3 mol%) 存在下在回流 Cl2 中进行，得到 RCH=CH B(O2C2Me4) 。
• Chiral Phosphoric Acid-Catalyzed Enantio- and Diastereoselective Allylboration of Aldehydes with β,γ-Substituted Allylboronates
  作者：Jinping Yuan、Pankaj Jain、Jon C. Antilla

  DOI：10.1021/acs.joc.2c00764

  日期：2022.6.17

  The catalytic asymmetric addition of β,γ-substituted allylboronates to aldehydes has been described. Promoted by 5 mol % chiral phosphoric acid, the reactions were broadly applicable, scalable, and efficient, allowing for the formation of 3,4-anti/syn-homoallylic alcohols bearing adjacent tertiary or quaternary stereogenic centers in a highly enantio- and diastereoselective manner (≤99% ee and dr >20:1)

  已经描述了 β,γ-取代的烯丙基硼酸酯对醛的催化不对称加成。在 5 mol% 手性磷酸的促进下，该反应具有广泛的适用性、可扩展性和高效性，允许以高度对映和非对映选择性的方式形成带有相邻叔或季立体中心的 3,4-反/同-高烯丙醇（≤99% ee 和 dr >20:1）。涉及手性磷酸的刚性椅子状过渡态有助于高度控制的反应。
• Unsaturated Fatty Alcohol Derivatives as a Source of Substituted Allylzirconocene
  作者：Nicka Chinkov、Anat Levin、Ilan Marek

  DOI：10.1002/anie.200501946

  日期：2006.1.9
• Selective mono- and polymethylene homologations of copper reagents using (iodomethyl)zinc iodide
  作者：AchyuthaRao Sidduri、Michael J. Rozema、Paul Knochel

  DOI：10.1021/jo00062a010

  日期：1993.5

  A wide range of unsaturated aryl-, alkenyl-, alkynylcopper compounds can be selectively homologated by a methylene unit using (iodomethyl)zinc iodide or bis(iodomethyl)zinc. These reactions allow the generation of mixed allylic zinc-copper compounds which can be efficiently trapped with carbonyl compounds. An application to a general preparation of functionalized alpha-methylene-gamma-butyrolactones is described. The homologation of alkynylcoppers with (iodomethyl)zinc iodide allows a one-pot preparation of propargylic copper reagents which in the presence of a carbonyl compound provide various homopropargylic alcohols in excellent yields. In the absence of an electrophile, a clean quadruple methylene homologation of alkynylcoppers occurs to furnish dienic copper reagents. The homologation of other types of copper reagents is also possible, and carbanions at the alpha-position to amines as well as homoenolates of aldehydes or ketones can also be prepared by this method.