γ-Phenyl-allylalkohol-methoxy-methylether | 91970-13-7

• 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: γ-Phenyl-allylalkohol-methoxy-methylether
• 英文别名: 3-(Methoxymethoxy)prop-1-enylbenzene
• CAS: 91970-13-7
• 化学式: C₁₁H₁₄O₂
• 分子量: 178.231
• InChiKey: WKWRCTSABBWVFC-UHFFFAOYSA-N

物化性质

• 沸点：
  92 °C(Press: 2 Torr)
• 密度：
  1.011±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  γ-Phenyl-allylalkohol-methoxy-methylether 在 2,2'-联吡啶 、 三氟甲磺酸三甲基硅酯 、 水 作用下， 以 二氯甲烷 、 乙醚 为溶剂， 反应 10.5h， 以81%的产率得到肉桂醇
  参考文献：
  名称：

  The reaction of acetal-type protective groups in combination with TMSOTf and 2,2′-bipyridyl; mild and chemoselective deprotection and direct conversion to other protective groups

  摘要：

  A mild and chemoselective deprotection method of various acetal-type protective groups, such as MOM, MEM, BOM, and SEM ethers, has been developed. The combination of TMSOTf and 2,2'-bipyridyl was very effective for the deprotection, and the reaction proceeded via the formation of pyridinium intermediates, which were hydrolyzed to the corresponding alcohols in good to high yields. The features of this method are mild (almost neutral) reaction conditions and the tolerability of acid-sensitive functional groups. This method is also applicable for the direct conversion of MOM ether to BOM or SEM ether using the appropriate alcohols instead of H2O. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.02.048
• 作为产物：
  描述：

  肉桂醇 、 氯甲基甲基醚 在 4-二甲氨基吡啶 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 γ-Phenyl-allylalkohol-methoxy-methylether
  参考文献：
  名称：

  Remarkable effect of 2,2′-bipyridyl: mild and highly chemoselective deprotection of methoxymethyl (MOM) ethers in combination with TMSOTf (TESOTf)–2,2′-bipyridyl

  摘要：

  2,2'-联吡啶的显著效果促成了甲氧基甲基（MOM）醚的温和且高度化学选择性的去保护方法的成功开发，该方法结合了TMSOTf（或TESOTf）和2,2'-联吡啶；该方法可以直接将MOM基团转化为其他醚类保护基团（例如苄氧基甲基）及相应的醇。

  DOI：

  10.1039/b907910f

文献信息

• Improved Zinc-Catalyzed Simmons–Smith Reaction: Access to Various 1,2,3-Trisubstituted Cyclopropanes
  作者：Éric Lévesque、Sébastien R. Goudreau、André B. Charette

  DOI：10.1021/ol500267w

  日期：2014.3.7

  The Simmons–Smith reaction of zinc carbenoids with alkenes is a powerful method to access cyclopropanes containing various substitution patterns. This work exploits the high reactivity of aryldiazomethanes toward zinc halides to generate aryl-substituted carbenoids catalytically. These carbenoids are able to cyclopropanate various alkenes diastereoselectively, including unfunctionalized substrates

  锌类胡萝卜素与烯烃的西蒙斯-史密斯反应是一种有效的方法，可用于获得含有各种取代模式的环丙烷。这项工作利用了芳基重氮甲烷对卤化锌的高反应活性，从而催化生成芳基取代的类胡萝卜素。这些类胡萝卜素能够非对映选择性地环化各种烯烃，包括未官能化的底物，如苯乙烯。可以修饰锌催化剂以容许使用游离的烯丙基醇。
• Continuous Flow Synthesis and Purification of Aryldiazomethanes through Hydrazone Fragmentation
  作者：Éric Lévesque、Simon T. Laporte、André B. Charette

  DOI：10.1002/anie.201608444

  日期：2017.1.16

  often contaminated with other reagents and by‐products, making it incompatible with many applications, especially in catalysis. Herein is reported a metal‐free continuous flow method for the production of aryldiazomethane solutions in a non‐coordinating solvent from easily prepared, bench‐stable sulfonylhydrazones. All by‐products are removed by an in‐line aqueous wash, leaving a clean, base‐free diazo

  富电子的重氮化合物（例如芳基重氮甲烷）是合成复杂结构的有力试剂，但与它们的毒性和不稳定性相关的风险通常会限制其使用。流动化学技术可以避免这些问题，因为可以在生产过程中使用危险中间体，从而避免了积累和处理。不幸的是，产生的物流经常被其他试剂和副产物污染，使其与许多应用不兼容，特别是在催化方面。本文报道了一种无金属连续流动法，该方法用于从易于制备的，台式稳定的磺酰基hydr在非配位溶剂中生产芳基重氮甲烷溶液。通过在线水洗除去所有副产物，留下干净的无碱重氮物流。
• High-valent [SnIV(Br8TPP)(OTf)2] as a highly efficient and reusable catalyst for selective methoxymethylation of alcohols and phenols: The effect of substituted bromines on the catalytic activity
  作者：Majid Moghadam、Shahram Tangestaninejad、Valiollah Mirkhani、Iraj Mohammadpoor-Baltork、Mostafa Khajehzadeh、Farshid Kosari、Mehdi Araghi

  DOI：10.1016/j.poly.2009.07.041

  日期：2010.1

  tin(IV)octabromotetraphenylporphyrinato trifluoromethanesulfonate, [SnIV(Br8TPP)(OTf)2], was used for selective methoxymethylation of alcohols and phenols with formaldehyde dimethyl acetal (FDMA) at room temperature. Different primary, secondary and tertiary alcohols as well as phenols were converted to their corresponding methoxymethyl ethers with FMDA in the presence of an electron deficient tin(IV) porphyrin

  摘要在室温下，高价锡（IV）八溴四苯基卟啉三氟甲烷磺酸盐[SnIV（Br8TPP）（OTf）2]用于用甲醛二甲基乙缩醛（FDMA）对醇和酚进行选择性甲氧基甲基化。在缺电子的锡（IV）卟啉存在下，使用FMDA将不同的伯，仲和叔醇以及苯酚转化为相应的甲氧基甲基醚。催化剂被重复使用了几次，而活性没有明显损失。
• Ionic liquid-induced conversion of methoxymethyl-protected alcohols into nitriles and iodides using [Hmim][NO3]
  作者：Jalil Noei、Arsalan Mirjafari

  DOI：10.1016/j.tetlet.2014.06.016

  日期：2014.8

  This Letter reports a one-pot efficient conversion of methoxymethyl-ethers into their corresponding nitriles and iodides using the ionic liquid, 1-methyl-3H-imidazolium nitrate ([Hmim][NO3]) under microwave irradiation. A variety of products were prepared in high yields using this method.

  这封信报道了在微波辐射下，使用离子液体1-甲基-3 H-咪唑鎓硝酸盐（[Hmim] [NO 3 ]）一锅有效地将甲氧基甲基醚转化为其相应的腈和碘化物。使用这种方法可以高收率制备各种产品。
• H3PW12O40–[bmim][FeCl4]: A novel and green catalyst-medium system for microwave-promoted selective interconversion of alkoxymethyl ethers into their corresponding nitriles, bromides and iodides
  作者：Iraj Mohammadpoor-Baltork、Majid Moghadam、Shahram Tangestaninejad、Valiolah Mirkhani、Arsalan Mirjafari

  DOI：10.1016/j.crci.2010.03.015

  日期：2010.12

  Résumé In the present work, the catalytic activity of 12-tungstophosphoric acid immobilized on [bmim][FeCl4] ionic liquid as a highly efficient and eco-friendly catalytic system for rapid and chemoselective direct conversion of MOM- or EOM-ethers into their corresponding nitriles, bromides and iodides under microwave irradiation is reported. In these reactions, the products are obtained in high yields. The catalyst exhibited remarkable reactivity and was reused several times.

  摘要 在本研究中，报道了将12-钨磷酸固定在[bmim][FeCl4]离子液体上的催化活性，作为一种高效且环保的催化体系，用于在微波辐照下快速且化学选择性地将MOM-或EOM-醚直接转化为相应的腈、溴化物和碘化物。在这些反应中，产物的得率很高。催化剂表现出显著的反应性，并且多次重复使用。