1-((1-cyclohexylbut-3-enyloxy)methyl)benzene | 137438-47-2

• 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: 1-((1-cyclohexylbut-3-enyloxy)methyl)benzene
• 英文别名: (1-benzyloxy-but-3-enyl)cyclohexane；1-cyclohexyl-1-(benzyloxy)-3-butene；benzyl 4-cyclohexylbuten-1-yl ether；1-Cyclohexylbut-3-enoxymethylbenzene
• CAS: 137438-47-2
• 化学式: C₁₇H₂₄O
• 分子量: 244.377
• InChiKey: VOQMSEGZFGBRGG-UHFFFAOYSA-N

物化性质

• 沸点：
  332.2±21.0 °C(Predicted)
• 密度：
  0.963±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-((1-cyclohexylbut-3-enyloxy)methyl)benzene 在 sodium hydroxide 、 臭氧 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.83h， 以57%的产率得到methyl 3-cyclohexyl-3-(benzyloxy)propanoate
  参考文献：
  名称：

  Oxidative cleavage of mono-, di-, and trisubstituted olefins to methyl esters through ozonolysis in methanolic sodium hydroxide

  摘要：

  The ozonolysis of alkenes in methanolic NaOH or NaOMe with CH2Cl2 as cosolvent leads directly to methyl esters. The procedure has been used to prepare various alpha-, beta, and omega-alkoxy esters, acyloxy esters, and alpha- and beta-N-acyl and N-sulfonyl esters from the appropriate unsaturated ethers, esters, and amides. Other examples include the formation of dimethyl octanedioate from cyclooctene (75% yield), dimethyl nonanedioate and methyl nonanoate from methyl oleate (77 and 78%, respectively), and tetradecanoic acid gamma-lactone from 2-methyl-2-hexadecen-6-ol (80% yield).

  DOI：

  10.1021/jo00066a019
• 作为产物：
  描述：

  phenylmethanol 在 氢氧化钾 、 三氟化硼乙醚 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 生成 1-((1-cyclohexylbut-3-enyloxy)methyl)benzene
  参考文献：
  名称：

  Highly Diastereoselective Intramolecular Allylation Reactions of Mixed Silyl-Substituted Acetals

  摘要：

  The reaction of preformed mixed acetals derived from (alpha-hydroxyalkyl)dimethylallylsilane with a number of aromatic and aliphatic aldehydes in the presence of Lewis acids results in a highly diastereoselective intramolecular allylation reaction. The reaction proceeds through a cyclic synclinal S-E' addition of the allylsilane to an intermediate oxocarbenium ion. The reaction occurs exclusively by an intramolecular process as determined by means of a cross-over experiment. The relative stereochemistry was determined by the conversion of one of the allylation products to a known (stereodefined) aldol-type product. A greater degree of diastereoselectivity is obtained by in-situ formation of an oxocarbenium ion from (alpha-hydroxyhexyl)dimethylallylsilane and an aldehyde in the presence of boron trifluoride etherate. The diastereoselectivity of the in-situ allylation reaction typically exceeds 100:1 in favor of the syn adduct. However, reactions with electron rich aryl aldehydes resulted in a diminished degree of diastereoselectivity. The initial product of the in-situ reaction is an unstable silyl fluoride which is readily hydrolyzed to a silanol derivative upon reaction with methanolic potassium hydroxide. The overall yield of the two-step process is greater than 80%. A method for the synthesis of more highly substituted (alpha-alkoxyalkyl)dimethylallylsilanes by allyl anion displacement of methoxide from silicon is also described. The methyl siloxane derivatives were obtained by ozonolytic cleavage of an unsubstituted allyl group in methanol.

  DOI：

  10.1021/jo9517048

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。
• Iron(III) Chloride-Catalyzed Convenient One-Pot Synthesis of Homoallyl Benzyl Ethers Starting from Aldehydes
  作者：Tsutomu Watahiki、Yusuke Akabane、Seiji Mori、Takeshi Oriyama

  DOI：10.1021/ol035019w

  日期：2003.8.1

  Iron(III) chloride-catalyzed effective allylation reactions of acetals with allyltrimethylsilane proceeded smoothly in high to excellent yields. In addition, this method could be applied to the one-pot synthesis of homoallyl benzyl ethers by a combination of dibenzyl acetalization of aldehydes and consecutive allylation of dibenzyl acetals.

  [反应：见正文]乙二醛与烯丙基三甲基硅烷的氯化铁催化的有效烯丙基化反应以高收率顺利进行。另外，该方法可以通过醛的二苄基乙缩醛化和二苄基乙缩醛的连续烯丙基化的组合而用于一锅合成高烯丙基苄基醚。
• The silyl modified sakurai (SMS) reaction. An efficient and versatile one-pot synthesis of homoallylic ethers
  作者：Abdelaziz Mekhalfia、István E Markó

  DOI：10.1016/s0040-4039(00)92306-2

  日期：1991.1

  An efficient and versatile preparation of homoallylic ethers from trimethylsilyl ethers, allyltrimethylsilane and carbonyl compounds is described. Some preliminary experiments, aimed at controlling the diastereofacial selection in the SMS reaction, are also reported.

  描述了由三甲基甲硅烷基醚，烯丙基三甲基硅烷和羰基化合物有效和通用地制备均烯丙基醚的方法。还报道了一些旨在控制SMS反应中非对映体选择的初步实验。
• Brønsted Acid-Catalyzed Three-Component Hosomi–Sakurai Reactions
  作者：Daniela Kampen、Arnaud Ladépêche、Gerrit Claßen、Benjamin List

  DOI：10.1002/adsc.200800036

  日期：2008.5.5

  Aldehydes react with silyl ethers or the corresponding alcohols and allylsilanes in the presence of catalytic amounts of 2,4-dinitrobenzenesulfonic acid (DNBA) to provide a wide range of homoallylic ethers in moderate to high yields.

  醛在催化量的2,4-二硝基苯磺酸（DNBA）的存在下与甲硅烷基醚或相应的醇和烯丙基硅烷反应，以中等至高收率提供各种均聚物。
• Novel Reactions of Ethylene Acetals with Silyl-Substituted Nucleophiles. A Mild and Efficient Procedure for the Synthesis of Homoallyl Alkyl Ethers and Unsymmetrical Dialkyl Ethers
  作者：Takeshi Suzuki、Takeshi Oriyama

  DOI：10.1080/00397919908086101

  日期：1999.4

  Abstract Efficient one-pot synthesis of homoallyl alkyl ethers and dialkyl ethers was performed by the allylation and reduction of ethylene acetals with allyltrimethylsilane and f-butyldimethylsilane, respectively, in the presence of alkoxytrimethylsilane.

  摘要 在烷氧基三甲基硅烷存在下，通过乙烯缩醛分别与烯丙基三甲基硅烷和叔丁基二甲基硅烷进行烯丙基化和还原反应，高效地一锅法合成高烯丙基烷基醚和二烷基醚。