2-benzyl-3-(4-chlorophenyl)acrylic acid methyl ester | 177838-00-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 2-benzyl-3-(4-chlorophenyl)acrylic acid methyl ester
• 英文别名: methyl (E)-2-benzyl-3-(4-chlorophenyl)acrylate；(E)-methyl 2-benzyl-3-(4-chlorophenyl)acrylate；(E)-2-benzyl-3-(4-chlorophenyl)-acrylic acid methyl ester；methyl (E)-2-benzyl-3-(4-chlorophenyl)prop-2-enoate
• CAS: 177838-00-5
• 化学式: C₁₇H₁₅ClO₂
• 分子量: 286.758
• InChiKey: XOHTUYJEXCQSQA-NTCAYCPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-benzyl-3-(4-chlorophenyl)acrylic acid methyl ester 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 作用下， 以 四氯化碳 为溶剂， 反应 6.0h， 生成
  参考文献：
  名称：

  蒙脱石 K10 粘土催化合成来自 Baylis-Hillman 加合物的取代 1-芳基茚

  摘要：

  使用 Mont. 从 Baylis-Hillman 加合物合成 1-芳基茚的环保方法。K10和微波组合作为催化剂体系和合成β-苯基-底物的方法...

  DOI：

  10.1246/cl.2005.1494
• 作为产物：
  描述：

  2-[(4-氯苯基)-羟基甲基]-丙烯酸甲酯 、 苯硼酸 在 chloro(1,5-cyclooctadiene)rhodium(I) dimer 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以71%的产率得到2-benzyl-3-(4-chlorophenyl)acrylic acid methyl ester
  参考文献：
  名称：

  Baylis–Hillman adducts in rhodium-catalyzed 1,4-additions: unusual reactivity

  摘要：

  在铑催化剂的作用下，未活化的 BaylisâHillman 加合物与芳基硼酸发生反应，生成三取代烯烃，且收率很高。这种高效反应（有氧条件、低温）被认为是通过一种意想不到的机制进行的，其中涉及 1,4-加成/δ-羟基消除步骤，而不是Ï-烯丙基型铑中间体。

  DOI：

  10.1039/b402928c

文献信息

• Silica Chloride-Catalyzed One-Pot Isomerization - Chlorination, Arylation, and Etherification of Baylis - Hillman Adducts
  作者：Ponnusamy Shanmugam、Baby Viswambharan、Vadivel Vaithiyanathan

  DOI：10.1071/ch07123

  日期：——

  silica chloride, an eco-friendly heterogeneous catalyst, silica chloride–arenes, and silica chloride–saturated and unsaturated alcohols as reagent systems are reported. These reactions furnished highly functionalized isomerized Baylis–Hillman derivatives in good yield. The efficiency and necessity of silica chloride catalyst was compared with thionyl chloride. A plausible mechanism of the reaction is proposed

  报道了一种方便有效的一锅异构化-氯化、芳基化和醚化几种 Baylis-Hillman 加合物与氯化硅、环保非均相催化剂、氯化硅-芳烃和氯化硅-饱和和不饱和醇作为试剂系统. 这些反应以良好的收率提供了高度官能化的异构化 Baylis-Hillman 衍生物。将氯化硅催化剂的效率和必要性与亚硫酰氯进行了比较。提出了一种似是而非的反应机理。
• Fe³⁺-K-10 Montmorillonite Clay Catalyzed Friedel–Crafts Reaction of Unactivated Baylis–Hillman Adducts: An Efficient Stereoselective Synthesis of Trisubstituted Alkenes Containing a Benzyl Substituent
  作者：Biswanath Das、Anjoy Majhi、Joydeep Banerjee、Nikhil Chowdhury、Katta Venkateswarlu

  DOI：10.1246/cl.2005.1492

  日期：2005.11

  The stereoselective synthesis of trisubstituted alkenes containing a benzyl substituent has been achieved by employing Friedel-Craft reaction of aromatic compounds with unactivated Baylis-Hillman adducts in the presence of Fe 3 + -K-10 montmorillonite clay as a heterogeneous catalyst. The catalyst can be recovered and reused.

  在 Fe 3 + -K-10 蒙脱石粘土作为非均相催化剂存在下，通过使用芳族化合物与未活化的 Baylis-Hillman 加合物的 Friedel-Craft 反应，实现了含有苄基取代基的三取代烯烃的立体选择性合成。催化剂可以回收再利用。
• The Friedel-Crafts reaction of the Baylis-Hillman adducts
  作者：Deevi Basavaiah、Marimganti Krishnamacharyulu、Rachakonda Suguna Hyma、Subramanian Pandiaraju

  DOI：10.1016/s0040-4039(97)00266-9

  日期：1997.3

  A simple and convenient methodology for the stereoselective construction of 2-benzyl substituted trisubstituted olefins via sulfuric acid catalyzed Fredel-Crafts reaction of benzene with Baylis-Hillman adducts is described.

  描述了一种简单方便的方法，用于通过硫酸催化苯与Baylis-Hillman加合物的立体催化构造2-苄基取代的三取代的烯烃。
• Rhodium Fluorapatite Catalyst for the Synthesis of Trisubstituted Olefins via Cross Coupling of Baylis−Hillman Adducts and Arylboronic Acids
  作者：M. Lakshmi Kantam、K. B. Shiva Kumar、B. Sreedhar

  DOI：10.1021/jo701982m

  日期：2008.1.1

  [GRAPHICS]For R-2 = CN, Z-isomer (99%) was obtained.Treatment of fluorapatite (prepared by incorporating basic species F- in apatite in situ by coprecipitation) with an aqueous solution of RhCl3 resulted in rhodium-exchanged fluorapatite catalyst (RhFAP), which successfully promoted cross coupling of Baylis-Hillman adducts with arylboronic acids to yield trisubstituted olefins. A variety of arylboronic acids and Baylis-Hillman adducts were converted to the corresponding trisubstituted olefins, demonstrating the versatility of the reaction. The reaction is highly stereoselective. RhFAP was recovered quantitatively by simple filtration and reused with almost consistent activity.
• Palladium-Catalyzed Cross-Coupling of Baylis−Hillman Acetate Adducts with Organosilanes
  作者：George W. Kabalka、Gang Dong、Bollu Venkataiah、Chunlan Chen

  DOI：10.1021/jo051177k

  日期：2005.11.1

  A cross-coupling reaction between acetates of Baylis-Hillman adducts and organosilanes is described. A nonconventional solvent poly(ethylene glycol) (PEG) is used as the reaction medium.