2-(1-phenylbut-3-enyloxy)ethanol | 162613-62-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(1-phenylbut-3-enyloxy)ethanol
• 英文别名: 3-oxo-4-phenyl-6-hepten-1-ol；4-Phenyl-3-oxahept-6-en-1-ol；2-(1-Phenylbut-3-enoxy)ethanol
• CAS: 162613-62-9
• 化学式: C₁₂H₁₆O₂
• 分子量: 192.258
• InChiKey: MJZZSXPXDVRODZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(1-phenylbut-3-enyloxy)ethanol 在 草酰氯 、 二甲基亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以98%的产率得到4-Phenyl-3-oxahept-6-enal
  参考文献：
  名称：

  Stereoselectivity of intramolecular cyclisations of nitrones derived from 3-oxahept-6-enals

  摘要：

  分子内[1,3]-双极环加成的亚硝基 33 来自 3-oxahept-6-enals 7，在 4 位或 5 位被取代，采用多种方法制备，可得到收率很高甚至非常好的环加成物 34-37，具有良好的立体选择性，尤其是当取代基邻近烯时。环化似乎是通过定义明确的过渡态构象进行的，这应该具有预测价值。

  DOI：

  10.1039/a905802h
• 作为产物：
  描述：

  4-Phenyl-3-oxahept-6-enoic acid 在 lithium aluminium tetrahydride 、 potassium carbonate 作用下， 以 乙醚 、 丙酮 为溶剂， 反应 22.0h， 生成 2-(1-phenylbut-3-enyloxy)ethanol
  参考文献：
  名称：

  Stereoselectivity of intramolecular cyclisations of nitrones derived from 3-oxahept-6-enals

  摘要：

  分子内[1,3]-双极环加成的亚硝基 33 来自 3-oxahept-6-enals 7，在 4 位或 5 位被取代，采用多种方法制备，可得到收率很高甚至非常好的环加成物 34-37，具有良好的立体选择性，尤其是当取代基邻近烯时。环化似乎是通过定义明确的过渡态构象进行的，这应该具有预测价值。

  DOI：

  10.1039/a905802h

文献信息

• Silicomolybdic acid supported on silica gel: an efficient catalyst for Hosomi–Sakurai reactions
  作者：Kaliyappan Murugan、Sankareswaran Srimurugan、Chinpiao Chen

  DOI：10.1016/j.tet.2011.05.093

  日期：2011.8

  Silicomolybdic acid that is supported on silica gel (50 wt %) efficiently catalyzes the high-yielding Hosomi–Sakurai allylation of carbonyl compounds by allyltrimethylsilane in the presence of benzyl alcohol. The reaction rates of inactive substrates and the yields were greatly increased when preformed acetals were used as substrates.

  在苄醇存在下，负载在硅胶上的硅钼酸（50 wt％）有效地催化了烯丙基三甲基硅烷对羰基化合物的高产率Hosomi-Sakurai烯丙基化。当使用预制的乙缩醛作为底物时，非活性底物的反应速率和产率大大提高。
• 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。
• Catalytic ring-opening allylation of cyclic acetals with allylsilanes using silica-alumina
  作者：Ken Motokura、Hirokazu Yoneda、Akimitsu Miyaji、Toshihide Baba

  DOI：10.1039/c005033d

  日期：——

  Ring-opening allylation of cyclic acetals has required stoichiometric amounts of Lewis acids. In this paper, catalytic ring-opening allylation in the presence of silica-alumina is reported. This ring-opening allylation showed high atom economy. Consecutive allylation/hydrolysis using silica-alumina afforded homoallyloxyalcohols in good to high yields.

  环状缩醛的开环烯基化反应需要使用计量量的路易斯酸。本文报道了在硅铝土的存在下进行催化的开环烯基化反应。该开环烯基化反应显示出高原子经济性。使用硅铝土进行连续的烯基化/水解反应能够以良至高的产率合成同烯基醇。
• Stereoselectivity of intramolecular cyclisations of nitrones derived from 3-oxahept-6-enals
  作者：Michael B. Gravestock、David W. Knight、Jennifer S. Lovell、Steven R. Thornton

  DOI：10.1039/a905802h

  日期：——

  Intramolecular [1,3]-dipolar cycloadditions of nitrones 33, derived from 3-oxahept-6-enals 7, substituted at either the 4- or 5-position and prepared using a variety of approaches, give good to excellent yields of the cycloadducts 34–37, with good levels of stereoselectivity, especially when the substituent is adjacent to the alkene. The cyclisations appear to proceed via well-defined transition state conformations which should be of predictive value.

  分子内[1,3]-双极环加成的亚硝基 33 来自 3-oxahept-6-enals 7，在 4 位或 5 位被取代，采用多种方法制备，可得到收率很高甚至非常好的环加成物 34-37，具有良好的立体选择性，尤其是当取代基邻近烯时。环化似乎是通过定义明确的过渡态构象进行的，这应该具有预测价值。