1-phenylhex-1,5-dien-3-ol | 13891-95-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: 1-phenylhex-1,5-dien-3-ol
• 英文别名: 1-phenylhexa-1,5-dien-3-ol；1-phenyl-1,5-hexadien-3-ol
• CAS: 13891-95-7
• 化学式: C₁₂H₁₄O
• 分子量: 174.243
• InChiKey: YQIKOSMMGKCOFA-UHFFFAOYSA-N

物化性质

• 沸点：
  110-111 °C(Press: 1 Torr)
• 密度：
  1.0021 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 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-phenylhex-1,5-dien-3-ol 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 vinylbenzalacetone
  参考文献：
  名称：

  一锅法氧化/烯丙基化/氧化顺序，直接从伯醇制备β，γ-不饱和酮

  摘要：

  已经开发了一种一锅法氧化/烯丙基化/氧化方法，用于将伯醇转化为β，γ-不饱和酮。该方法已经应用于多种醇，并且在某些情况下，已经进行异构化以产生相应的α，β-不饱和酮。

  DOI：

  10.1016/j.tetlet.2011.03.033
• 作为产物：
  描述：

  (3-(methoxymethoxy)hexa-1,5-dien-1-yl)benzene 在 五氯化铌 作用下， 以 乙腈 为溶剂， 反应 1.5h， 以80%的产率得到1-phenylhex-1,5-dien-3-ol
  参考文献：
  名称：

  NbCl 5介导的甲氧基甲基醚的脱保护

  摘要：

  描述了使用NbCl 5有效裂解甲氧基甲基醚。该协议可与烷基，烯丙基，炔丙基，苄醇和苯酚衍生物的MOM醚有效地协同工作。还发现在当前条件下MOM酯可被有效地裂解。

  DOI：

  10.1016/j.tetlet.2009.03.171

文献信息

• Porous and Robust Lanthanide Metal-Organoboron Frameworks as Water Tolerant Lewis Acid Catalysts
  作者：Yan Liu、Ke Mo、Yong Cui

  DOI：10.1021/ic400598x

  日期：2013.9.16

  number of isolated Lewis acid B(III) and Ln(III) sites on the pore surfaces. The Nd-MOF assisted with sodium dodecylsulfate was found to be highly effective, recyclable, and reusable heterogeneous catalyst for the carbonyl allylation reaction, the Diels–Alder reaction, and the Strecker-type reaction in water. The transformations were cocatalyzed by Nd(III) and B(III) Lewis acids, with activities much

  多孔且坚固的12连接金属-有机骨架（MOF）是通过将四核镧系（Ln）碳酸酯簇与有机硼衍生的三羧酸酯桥联配体连接而构建的。高连接性的Ln-MOF具有出色的热稳定性和水解稳定性，并且在孔表面具有大量的孤立的路易斯酸B（III）和Ln（III）位。发现Nd-MOF辅以十二烷基硫酸钠可用于水中的羰基烯丙基化反应，Diels-Alder反应和Strecker型反应，是高效，可回收和可重复使用的非均相催化剂。Nd（III）和B（III）Lewis酸可共同催化转化，其活性远高于有机硼和镧系元素对应物及其混合物的活性。
• Strong Lewis Acids of Air-Stable Metallocene Bis(perfluorooctanesulfonate)s as High-Efficiency Catalysts for Carbonyl-Group Transformation Reactions
  作者：Renhua Qiu、Xinhua Xu、Lifeng Peng、Yalei Zhao、Ningbo Li、Shuangfeng Yin

  DOI：10.1002/chem.201103874

  日期：2012.5.14

  that 2 a and 2 b were thermally stable at 300 and 180 °C, respectively. These complexes exhibited unusually high solubility in polar organic solvents. Conductivity measurement showed that the complexes (2 a and 2 b) were ionic dissociation in CH3CN solution. X‐ray analysis result confirmed 2 a⋅3 H2O⋅THF was a cationic organometallic Lewis acid. UV/Vis spectra showed a significant red shift due to the

  强路易斯酸空气中稳定的金属茂双（全氟辛烷磺酸盐）S [M（CP）2 ] [OSO 2 C ^ 8 ˚F 17 ] 2 ⋅ Ñ ħ 2 O⋅THF（M = Zr的（2 ⋅3ħ 2 O⋅THF ），M =的Ti（图2b ⋅2ħ 2 O⋅THF））由[M（CP）的反应合成2 ]氯2（M = Zr的（1），M =的Ti（图1b）），与n BuLi和C 8 F 17 SO 3 H（2当量）或与C 8 F 17 SO 3Ag（2当量）。这些配合物的水合物数（n）是可变的，取决于条件从0变为4。与众所周知的茂金属三氟甲磺酸盐相反，这些络合物在露天环境中一年没有变化。热重-差示扫描量热（TG-DSC）分析表明，2和图2b分别为300和180℃，是热稳定的。这些配合物在极性有机溶剂中显示出异常高的溶解度。电导率测量表明，络合物（2a和2b）在CH 3 CN溶液中呈离子离解。X射线分析结果确认为2 a⋅3H
• Allylation of aldehydes by dual photoredox and nickel catalysis
  作者：Andrea Gualandi、Giacomo Rodeghiero、Adriana Faraone、Filippo Patuzzo、Marianna Marchini、Francesco Calogero、Rossana Perciaccante、Thomas Paul Jansen、Paola Ceroni、Pier Giorgio Cozzi

  DOI：10.1039/c9cc03344k

  日期：——

  Here we report the application of dual nickel/photoredox catalysis to the allylation of aliphatic, aromatic and heteroaromatic aldehydes by using commercially available reagents. The process utilizes the combination of a Ni(II) complex, [Ru(bpy)3]2+ as a photoredox catalyst, and allylacetate under blue LED irradiation, and allows the synthesis of a large variety of homoallylic alcohols.

  在这里，我们报道了通过使用可商购的试剂，镍/光氧化还原双重催化在脂肪族，芳香族和杂芳香族醛的烯丙基化中的应用。该方法利用了Ni（II）配合物，[Ru（bpy）3 ] 2+作为光氧化还原催化剂和乙酸烯丙酯在蓝色LED照射下的组合，可以合成多种均烯丙基醇。
• Palladium-catalyzed intramolecular carbonyl allylation via Claisen rearrangement
  作者：Yoshiro Masuyama、Yumiko Nimura、Yasuhiko Kurusu

  DOI：10.1016/s0040-4039(00)79019-8

  日期：1992.10

  Palladium-catalyzed intramolecular carbonyl allylation with SnCl2 by 5-substituted 4-methylene-5-(2-tetrahydropranyloxy)pentanals, prepared by Claisen rearrangement of 2-[1-(2-tetrahydropyranyloxy)alkyl]allyl vinyl ethers, occurred radioselectively at ambient temperature in DMI/H2O to give 2-substituted 3-methylenecyclopentanols in good yields.

  通过2- [1-（2-（4-四氢吡喃氧基）烷基]烯丙基乙烯基醚的克莱森重排制备的5-取代的4-亚甲基-5-（2-四氢戊氧基）戊醛与SnCl 2进行钯催化的分子内羰基烯丙基化反应，于在DMI / H 2 O中的室温下以良好的产率得到2-取代的3-亚甲基环戊醇。
• Facile Preparation of Allylzinc Species from Allyl Bromides and Unactivated Zinc Induced by a Catalytic Amount of Aluminum Chloride and Their Reactions with Carbonyl Compounds and Acetals.
  作者：Hatsuo MAEDA、Kazushige SHONO、Hidenobu OHMORI

  DOI：10.1248/cpb.42.1808

  日期：——

  The effects of Lewis acids (ZnCl2, AlCl3, BF3, and TiCl4) on the generation of allylzinc species from allyl bromide and unactivated zinc powder in dry tetrahydrofuran (THF) were examined by trapping the organozinc compound with benzaldehyde, that is, Grignard-type allylation of the aldehyde. Among the Lewis acids employed, AlCl3, was found to be the promoter of choice. The allylzinc species preformed in the presence of a catalytic amount of AlCl3 effectively allylated carbonyl compounds. Various aromatic and aliphatic aldehydes as well as ketones were converted into homoallylic alcohols in good to excellent yields. Under the reaction conditions employed, ester, hydroxy, acetal, and aromatic nitro and halide groups were tolerated. In the case of α, β-unsaturated carbonyl compounds, selective 1, 2-addition was observed. Substituted allyl bromides such as prenyl, crotyl, cinnamyl, and 2-cyclohexenyl bromides were smoothly converted to the corresponding allylzinc compounds, which reacted with carbonyl compounds to give substituted homoallylic alcohols in excellent yields. The diastereoselectivity in crotylation, cinnamylation, and 2-cyclohexenylation depended upon the structures of both the organic metals and the electrophiles. The origin of the observed selectivity is discussed. The allylation of dimethyl and cyclic acetals accompanied with carbon-oxygen bond cleavege also proceeded in excellent yields provided that two equivalents of AlCl3 was present.

  在干燥的四氢呋喃（THF）中，研究了路易斯酸（ZnCl2、AlCl3、BF3和TiCl4）对烯丙基溴和未活化的锌粉生成烯丙基锌物种的影响，并通过苯甲醛捕获有机锌化合物，即醛的格氏型烯丙基化反应。在所用的路易斯酸中，AlCl3被发现是最优的促进剂。在催化量的AlCl3存在下预形成的烯丙基锌物种能有效地烯丙基化羰基化合物。各种芳香族和脂肪族醛以及酮被转化为同烯丙基醇，产率良好至优秀。在所采用的反应条件下，酯、羟基、缩醛以及芳香族硝基和卤素基团均被容忍。对于α,β-不饱和羰基化合物，观察到了选择性的1,2-加成。取代的烯丙基溴如香叶基、巴豆基、肉桂基和2-环己烯基溴均能顺利转化为相应的烯丙基锌化合物，这些化合物与羰基化合物反应生成取代的同烯丙基醇，产率极佳。在巴豆基化、肉桂基化和2-环己烯基化中的立体选择性取决于有机金属和亲电试剂的结构。讨论了观察到的选择性的起源。在AlCl3的两当量存在下，伴随着碳-氧键断裂的二甲基和环状缩醛的烯丙基化也以极佳的产率进行。