2-烯丙基-1,3-二甲基苯 | 1587-05-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-烯丙基-1,3-二甲基苯
• 英文名称: 2-allyl-1,3-dimethylbenzene
• 英文别名: 3-(2,6-Dimethylphenyl)-1-propene；1,3-dimethyl-2-prop-2-enylbenzene
• CAS: 1587-05-9
• 化学式: C₁₁H₁₄
• mdl: MFCD09801219
• 分子量: 146.232
• InChiKey: DPIFGUSZRIMEPH-UHFFFAOYSA-N

物化性质

• 沸点：
  78 °C(Press: 12 Torr)
• 密度：
  0.878±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• 海关编码：
  2902909090

反应信息

• 作为反应物：
  描述：

  2-烯丙基-1,3-二甲基苯 在 三(五氟苯基)硼烷 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以98%的产率得到(E)-1,3-dimethyl-2-(prop-1-en-1-yl)benzene
  参考文献：
  名称：

  B(C6F5)3-催化烯烃的E选择性异构化

  摘要：

  Move along !：在此，我们报道了 B(C 6 F 5 ) 3 -催化的E -烯烃选择性异构化。不含过渡金属的方法适用于各种易于获得的底物，可获得范围广泛的合成有用产品，其中包含多功能立体定义的内部烯烃。合成和计算机理研究表明，异构化沿着竞争性 1,2-氢化物转移和氢化物提取途径进行。

  DOI：

  10.1002/chem.202202454
• 作为产物：
  描述：

  2,6-二甲基苯酚 在 bis-triphenylphosphine-palladium(II) chloride 、 三苯基膦 、 lithium chloride 2,4,6-三甲基吡啶 、 2,6-二叔丁基-4-甲基苯酚 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 2-烯丙基-1,3-二甲基苯
  参考文献：
  名称：

  Palladium-catalyzed cross-coupling reactions of highly hindered, electron-rich phenol triflates and organostannanes

  摘要：

  The palladium-catalyzed cross-coupling reaction of highly hindered, electron-rich phenol triflates and organostannanes (Stille reaction) has been studied in a systematic manner. The following are its salient features: (1) electron-rich phenol triflates require triphenylphosphine to undergo palladium-catalyzed cross-couplings; (2) in general, efficient reactions take place only when larger-than-usual amounts (10-15%) of palladium are employed. On the reagent side, alkyl- (methyl only), allyl-, vinyl- and alkinylstannanes undergo efficient cross-couplings with the title substrates. However, some limitations to this novel entry to 2-substituted resorcinols exist in regard to both substrates and reagents. Thus, conformationally rigid (hexasubstituted) aryl triflates behave poorly, demethylation being an important side reaction. Moreover, alkyl groups other than methyl cannot be introduced because beta-elimination occurs more rapidly. The potentially powerful synthesis of hindered biaryls has also been studied briefly. In the present conditions, the reaction appears to be limited by the presence of ortho substituents on the arylstannane moiety.

  DOI：

  10.1021/jo00028a051

文献信息

• A Highly Effective (Triphenyl phosphite)palladium Catalyst for a Cross?Coupling Reaction of Allylic Alcohols with Organoboronic Acids
  作者：Yoshihito Kayaki、Takashi Koda、Takao Ikariya

  DOI：10.1002/ejoc.200400621

  日期：2004.12

  reaction of aryl and vinyl boronic acids and allylic alcohols proceeded smoothly in toluene or dioxane in the presence of a (triphenyl phosphite)palladium catalyst to give the corresponding allylbenzene derivatives and 1,4-dienes. Neither cocatalysts for promoting C−O bond cleavage of allylic alcohols nor bases for activation of organoboron reagents are required for promoting the coupling process. (© Wiley-VCH

  在（亚磷酸三苯酯）钯催化剂存在下，芳基和乙烯基硼酸与烯丙醇在甲苯或二恶烷中的交叉偶联反应顺利进行，得到相应的烯丙基苯衍生物和1,4-二烯。促进偶联过程不需要用于促进烯丙醇的 CO 键断裂的助催化剂和用于活化有机硼试剂的碱。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
• Linear Hydroaminoalkylation Products from Alkyl‐Substituted Alkenes
  作者：Michael Warsitz、Sven Doye

  DOI：10.1002/chem.202003223

  日期：2020.11.26

  alkyl‐substituted alkenes into linear hydroaminoalkylation products represents a strongly desirable synthetic transformation. In particular, such conversions of N‐methylamine derivatives are of great scientific interest, because they would give direct access to important amines with unbranched alkyl chains. Herein, we present a new one‐pot procedure that includes an initial alkene hydroaminoalkylation with an

  烷基取代的烯烃向线性氢氨基烷基化产物的区域选择性转化代表了非常理想的合成转化。特别是N的这种转换甲胺衍生物具有极大的科学意义，因为它们可以直接获得具有直链烷基链的重要胺。在本文中，我们提出了一种新的单锅法，其中包括使用α-甲硅烷基化的胺底物进行的初始烯烃加氢烷基化反应和随后的原去烷基化反应，该反应可从简单的烷基取代的烯烃中以较高的选择性提供线性的加氢氨基烷基化产物。为此，已经开发出了新型的钛催化剂，它们能够激活更具挑战性的α-硅烷化胺底物的α-CH键。另外，描述了新催化剂的配体结构与所获得的区域选择性之间的直接关系。
• Metal‐Free Photochemical Olefin Isomerization of Unsaturated Ketones via 1,5‐Hydrogen Atom Transfer
  作者：Rajendran Manikandan、Ravindra S. Phatake、N. Gabriel Lemcoff

  DOI：10.1002/chem.202200634

  日期：2022.5.19

  Bring on the Light: An efficient photochemical metal/catalyst-free system has been uncovered for the selective one-bond olefin migration of unsaturated ketones. Diverse substrate scope, functional group tolerance and its application for dehomologation and one-carbon selective olefin migration processes in linear alkenes highlights the usefulness of this method.

  带来光明：已经发现了一种有效的光化学无金属/催化剂体系，用于不饱和酮的选择性单键烯烃迁移。多种底物范围、官能团耐受性及其在线性烯烃中的去同源化和单碳选择性烯烃迁移过程中的应用突出了该方法的实用性。
• Diastereoselective Access to anti-β-Hydroxy Sulfoxides from ­Chiral Epoxides and Prochiral Sulfenate Anions: Mechanistic ­Insights, Scope, and Limitation
  作者：Ken Ohmori、Jian Zhang、Vipul V. Betkekar、Keisuke Suzuki

  DOI：10.1055/a-2196-5592

  日期：——

  route to anti-β-hydroxy sulfoxides through the reaction of epoxides with sulfenate anions. Extensive experimental/computational studies revealed the dual special roles of MgBr2·OEt2, serving to generate the bromohydrin alkoxide intermediate, which undergoes nucleophilic attack on the prochiral sulfenate in a diastereoselective manner. The present study has opened a general stereoselective synthetic

  本文报道了通过环氧化物与磺酸根阴离子的反应获得抗β-羟基亚砜的立体选择性途径。广泛的实验/计算研究揭示了 MgBr2·OEt2 的双重特殊作用，用于生成溴醇醇盐中间体，该中间体以非对映选择性方式对前手性次磺酸盐进行亲核攻击。本研究开辟了抗β-羟基亚砜的通用立体选择性合成路线。
• Palladium Nanoparticles in Glycerol: A Versatile Catalytic System for CX Bond Formation and Hydrogenation Processes
  作者：Faouzi Chahdoura、Christian Pradel、Montserrat Gómez

  DOI：10.1002/adsc.201300753

  日期：2013.12.16

  AbstractPalladium nanoparticles stabilised by tris(3‐sulfophenyl)phosphine trisodium salt in neat glycerol have been synthesised and fully characterised, starting from both Pd(II) and Pd(0) species. The versatility of this innovative catalytic colloidal solution has been proved by its efficient application in CX bond formation processes (X=C, N, P, S) and CC multiple bond hydrogenation reactions. The catalytic glycerol phase could be recycled more than ten times, preserving its activity and selectivity. The scope of each of these processes has demonstrated the power of the as‐prepared catalyst, isolating the corresponding expected products in yields higher than 90%. The dual catalytic behaviour of this glycerol phase, associated to the metallic nanocatalysts used in wet medium (molecular‐ and surface‐like behaviour), has allowed attractive applications in one‐pot multi‐step transformations catalysed by palladium, such as CC coupling followed by hydrogenation, without isolation of intermediates using only one catalytic precursor.magnified image