2-bromo-1-methyl-4-vinylbenzene | 167960-11-4

• 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-bromo-1-methyl-4-vinylbenzene
• 英文别名: 2-Bromo-4-ethenyl-1-methylbenzene
• CAS: 167960-11-4
• 化学式: C₉H₉Br
• 分子量: 197.074
• InChiKey: XDMTVCPQOZZZPA-UHFFFAOYSA-N

物化性质

• 沸点：
  235.1±19.0 °C(Predicted)
• 密度：
  1.332±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  2-bromo-1-methyl-4-vinylbenzene 在 1,3-二溴-5,5-二甲基海因 、 水 作用下， 反应 3.0h， 生成 唑吡坦杂质
  参考文献：
  名称：

  由1,3-二溴-5,5-二甲基乙内酰脲（DBH）介导的苯乙烯衍生物合成2-氨基噻唑

  摘要：

  据报道，通过DBH介导的苯乙烯和硫脲的氧化环化合成2-氨基噻唑的有效方法。使用DBH作为溴源和氧化剂，通过两步一锅法成功地将各种烯烃成功转化为相应的2-氨基噻唑，产率为10-81％。该方法可以容易地以克为单位进行，并且成功地用于以苯乙烯为起始原料的抗炎药fanetizole的合成。

  DOI：

  10.1016/j.tet.2018.05.021
• 作为产物：
  描述：

  3'-溴-4'-甲基苯乙酮 在 potassium hydrogensulfate 、 lithium aluminium tetrahydride 、 对苯二酚 作用下， 以 乙醚 为溶剂， 20.0~102.0 ℃ 、399.97 Pa 条件下， 生成 2-bromo-1-methyl-4-vinylbenzene
  参考文献：
  名称：

  Preparation of polystyrene-supported soluble palladacycle catalyst for Heck and Suzuki reactions

  摘要：

  A polystyrene-supported palladium complex soluble in tetrahydrofuran and N,N-dimethylacetamide and precipitated in diethyl ether or acetonitrile was prepared from two routes as an excellent and recyclable palladacycle catalyst for carbon-carbon bond formation in Heck and Suzuki reactions to give high yields of the desired products. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.04.036

文献信息

• 1,3-Dibromo-5,5-dimethylhydantoin mediated oxidative amidation of terminal alkenes in water
  作者：Chunhua Ma、Guojie Fan、Ping Wu、Zhi Li、Yang Zhou、Qingjie Ding、Wei Zhang

  DOI：10.1039/c7ob02329d

  日期：——

  variety of terminal alkenes were converted to the corresponding amides in yields of 25 to 86% in water via treatment with 1,3-dibromo-5,5-dimethylhydantoin, followed by reaction with molecular iodine and aq. NH3 (or amine) in one pot. This metal- and organic solvent-free protocol is not only suitable for styrene derivatives, but also, for the first time, works well on terminal aliphatic alkenes.

  通过用1，3-二溴-5，5-二甲基乙内酰脲处理，然后与分子碘和HCl水溶液反应，将多种末端烯烃在水中以25-86％的产率转化为相应的酰胺。一锅中加入NH 3（或胺）。这种无金属和有机溶剂的方案不仅适用于苯乙烯衍生物，而且首次在末端脂族烯烃上效果很好。
• Cobalt‐Catalyzed Radical Hydroamination of Alkenes with <i>N</i> ‐Fluorobenzenesulfonimides
  作者：Tao Qin、Guowei Lv、Qi Meng、Ge Zhang、Tao Xiong、Qian Zhang

  DOI：10.1002/anie.202110178

  日期：2021.12

  N-fluorobenzenesulfonimide (NFSI) and its analogues as both nitrogen source and oxidant was successfully disclosed. A variety of alkenes, including aliphatic alkenes, styrenes, α, β-unsaturated esters, amides, acids, as well as enones, were all compatible to provide desired amination products. Mechanistic experiments suggest that the reaction underwent a metal-hydride-mediated hydrogen atom transfer (HAT) with alkene

  成功地公开了使用 Co(salen) 作为催化剂、N-氟苯磺酰亚胺 (NFSI) 及其类似物作为氮源和氧化剂的烯烃的有效和通用自由基加氢胺化。各种烯烃，包括脂肪族烯烃、苯乙烯、α, β-不饱和酯、酰胺、酸以及烯酮，都可以提供所需的胺化产物。机理实验表明，该反应与烯烃进行了金属氢化物介导的氢原子转移 (HAT)，然后是关键的催化剂控制原位生成的有机钴 (IV) 物质和氮基亲核试剂之间的类 SN 2 途径。此外，借助改性手性钴 (II)-salen 催化剂，还实现了前所未有的不对称版本，具有良好到出色的对映控制水平。
• The Catalytic Asymmetric Intermolecular Prins Reaction
  作者：C. David Díaz-Oviedo、Rajat Maji、Benjamin List

  DOI：10.1021/jacs.1c10245

  日期：2021.12.15

  Despite their significant potential, catalytic asymmetric reactions of olefins with formaldehyde are rare and metal-free approaches have not been previously disclosed. Here we describe an enantioselective intermolecular Prins reaction of styrenes and paraformaldehyde to form 1,3-dioxanes, using confined imino-imidodiphosphate (iIDP) Brønsted acid catalysts. Isotope labeling experiments and computations

  尽管它们具有巨大的潜力，但烯烃与甲醛的催化不对称反应是罕见的，并且以前没有公开过不含金属的方法。在这里，我们描述了苯乙烯和多聚甲醛的对映选择性分子间 Prins 反应以形成 1,3-二恶烷，使用受限的亚氨基-亚氨基二磷酸 ( i IDP) 布朗斯台德酸催化剂。同位素标记实验和计算表明酸活化甲醛低聚物向烯烃中的协同、高度异步添加。对映体富集的 1,3-二恶烷可以转化为相应的光学活性 1,3-二醇，它们是有价值的合成构件。
• Total Synthesis and Antibiotic Properties of Amino‐Functionalized Aromatic Terpenoids Related to Erogorgiaene and the Pseudopterosins
  作者：Christian Eric Schumacher、Marvin Rausch、Tobias Greven、Jörg‐Martin Neudörfl、Tanja Schneider、Hans‐Günther Schmalz

  DOI：10.1002/ejoc.202200058

  日期：2022.7.14

  An additional amino-alkyl side chain makes the difference: A series of amino-functionalized analogs of marine diterpenoids were prepared by stereoselective total synthesis and characterized with respect to their antibiotic properties. While the phenolic intermediates showed activity only against Gram-positive bacteria, the amines proved to be active also against Gram-negative bacterial strains.

  额外的氨基-烷基侧链产生了影响：通过立体选择性全合成制备了一系列氨基官能化的海洋二萜类似物，并对其抗生素特性进行了表征。虽然酚类中间体仅显示对革兰氏阳性细菌的活性，但胺证明对革兰氏阴性细菌菌株也有活性。
• Polystyrene-supported palladacycle catalysts
  申请人：Luo Fen-Tair

  公开号：US20060004216A1

  公开（公告）日：2006-01-05

  This invention relates to a recyclable palladacycle catalyst of formula in which each is a single bond or a double bond, provided that if one is a double bond, its neighboring is not a double bond; each of X and Z, independently, is —P(R′)—, —S—, —N(R′)—, or —N═, in which R′ is alkyl, aryl, cyclyl, heteroaryl, or heterocyclyl; each of Y 1 and Y 2 , independently, is an anion of an organic or inorganic acid; each of X 1 , X 2 , X 3 , Z 1 , Z 2 , and Z 3 , independently, is —C═, —CR″—, in which R″ is H, alkyl, aryl, cyclyl, heteroaryl, or heterocyclyl; and each of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 , independently, is H, alkyl, aryl, cyclyl, heteroaryl, or heterocyclyl, or R 1 , X, X 1 , and R 2 , together form a 3-8 membered ring, or R 2 , X 1 , X 2 , and R 3 , together form a 3-8 membered ring, or R 3 , X 2 , X 3 , and R 4 , together form a 3-8 membered ring, or R 5 , Z, Z 1 , and R 6 , together form a 3-8 membered ring, or R 6 , Z 1 , Z 2 , and R 7 , together form a 3-8 membered ring, or R 7 , Z 2 , Z 3 , and R 8 , together form a 3-8 membered ring; provided that one of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 , or the ring formed from R 1 , X, X 1 , and R 2 , or the ring formed from R 2 , X 1 , X 2 , and R 3 , or the ring formed from R 3 , X 2 , X 3 , and R 4 , or the ring formed from R 5 , Z, Z 1 , and R 6 , or the ring formed from R 1 , Z 1 , Z 2 , and R 7 , or the ring formed from R 7 , Z 2 , Z 3 , and R 8 is connected to a first polymer. Also included in this invention are a method of promoting a coupling reaction using the above-described palladacycle compound and a method of making it.

  本发明涉及一种可回收的钯环化合物催化剂，其化学式为其中每个是单键或双键，前提是如果其中一个是双键，则其相邻的不是双键；每个X和Z独立地是-P（R′）-，-S-，-N（R′）-或-N═，其中R′是烷基，芳基，环烷基，杂芳基或杂环烷基；每个Y1和Y2独立地是有机或无机酸的阴离子；每个X1、X2、X3、Z1、Z2和Z3独立地是-C═或-CR″-，其中R″是H，烷基，芳基，环烷基，杂芳基或杂环烷基；每个R1、R2、R3、R4、R5、R6、R7和R8独立地是H，烷基，芳基，环烷基，杂芳基或杂环烷基，或者R1、X、X1和R2一起形成一个3-8成员环，或者R2、X1、X2和R3一起形成一个3-8成员环，或者R3、X2、X3和R4一起形成一个3-8成员环，或者R5、Z、Z1和R6一起形成一个3-8成员环，或者R6、Z1、Z2和R7一起形成一个3-8成员环，或者R7、Z2、Z3和R8一起形成一个3-8成员环；前提是R1、R2、R3、R4、R5、R6、R7和R8中的一个，或由R1、X、X1和R2形成的环，或由R2、X1、X2和R3形成的环，或由R3、X2、X3和R4形成的环，或由R5、Z、Z1和R6形成的环，或由R1、Z1、Z2和R7形成的环，或由R7、Z2、Z3和R8形成的环之一连接到第一个聚合物。本发明还包括使用上述钯环化合物促进偶联反应的方法以及制备该化合物的方法。