phenyl trans-p-chlorocinnamate | 444666-99-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: phenyl trans-p-chlorocinnamate
• 英文别名: phenyl 4-chlorocinnamate；(E)-3-(4-chlorophenyl)acrylic acid phenyl ester；(E)-phenyl 3-(4-chlorophenyl)acrylate；4-chloro-trans-cinnamic acid phenyl ester；4-Chlor-trans-zimtsaeure-phenylester；phenyl (E)-3-(4-chlorophenyl)prop-2-enoate
• CAS: 444666-99-3
• 化学式: C₁₅H₁₁ClO₂
• 分子量: 258.704
• InChiKey: RHASUMGLHNXWEW-DHZHZOJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  phenyl trans-p-chlorocinnamate 生成 1-氯-4-[(e)-2-苯基乙烯基]苯
  参考文献：
  名称：

  Skraup; Beng, Chemische Berichte, 1927, vol. 60, p. 946

  摘要：

  DOI：
• 作为产物：
  描述：

  对氯肉桂酸 在 三氯化磷 作用下， 生成 phenyl trans-p-chlorocinnamate
  参考文献：
  名称：

  Skraup; Beng, Chemische Berichte, 1927, vol. 60, p. 946

  摘要：

  DOI：

文献信息

• Palladium-Catalyzed Hydroesterification of Alkynes Employing Aryl Formates without the Use of External Carbon Monoxide
  作者：Yuko Katafuchi、Tetsuaki Fujihara、Tomohiro Iwai、Jun Terao、Yasushi Tsuji

  DOI：10.1002/adsc.201000750

  日期：2011.2.11

  highly efficient hydroesterification of alkynes employing aryl formates has been developed without the use of external carbon monoxide and at ambient pressure. The reaction in the presence of a palladium-xantphos catalyst system selectively affords α,β-unsaturated esters in good to high yields. Use of an aryl formate is crucial and alkyl formates did not react at all. The hydroesterification of norbornene

  已经开发了在不使用外部一氧化碳的情况下并且在环境压力下使用芳基甲酸酯的炔烃的高效加氢酯化。在钯-黄磷催化剂体系存在下的反应以良好至高收率选择性地提供α，β-不饱和酯。甲酸芳基酯的使用至关重要，烷基甲酸酯根本不反应。降冰片烯和末端烯烃的加氢酯化也容易在相似的反应条件下进行。机理研究表明，加氢酯化过程中发生了芳基甲酸酯向一氧化碳和苯酚衍生物的转化。Xantphos作为芳基甲酸酯的转化和加氢酯化反应的配体都是非常有效的。
• Silver-Catalyzed Cross-Olefination of Donor and Acceptor Diazo Compounds: Use of<i>N</i>-Nosylhydrazones as Diazo Surrogate
  作者：Zhaohong Liu、Binbin Liu、Xue-Feng Zhao、Yan-Bo Wu、Xihe Bi

  DOI：10.1002/ejoc.201601610

  日期：2017.1.26

  The cross-olefination reaction of donor and acceptor diazo compounds is reported. The use of N-nosylhydrazones as the diazo surrogates and the dependence on silver catalysis are crucial for the reaction development. A variety of (hetero)aryl N-nosylhydrazones and α-diazo esters, amides, and phosphonates were compatible, affording functionalized alkenes in good-to-high yields with moderate Z/E selectivity

  报道了供体和受体重氮化合物的交叉烯烃化反应。使用 N-nosylhydrazones 作为重氮替代物和对银催化的依赖对于反应发展至关重要。各种（杂）芳基 N-nosylhydrazones 和 α-重氮酯、酰胺和膦酸酯是相容的，以良好到高的产率提供功能化烯烃，Z/E 选择性适中。实验和 DFT 计算结果表明交叉选择性是由于银催化剂对供体重氮化合物的选择性活化。
• Lipophilic NHC assisted one-pot synthesis of syncarpamide analogues in aqueous medium
  作者：Pavithira Suresh、Subramaniapillai Selva Ganesan

  DOI：10.1039/c9nj00134d

  日期：——

  Lipophilic NHC catalysis in aqueous medium was reported for the synthesis of biologically relevant (a)symmetrically substituted and unsymmetrically substituted syncarpamide analogues. All the reported reactions were performed in the absence of any expensive metal salts or additives. A diverse array of syncarpamide analogues was obtained in good yields. Lipophilic NHC catalysis was also extended to

  据报道在水性介质中的亲脂性NHC催化可合成生物学上相关的（a）对称取代和非对称取代的syncarpamide类似物。所有报道的反应均在不存在任何昂贵的金属盐或添加剂的情况下进行。以高收率获得了各种各样的辛卡酰胺类似物。亲脂性NHC催化也扩展到化学选择性酯交换反应。
• Dinuclear Zinc Catalyzed Asymmetric Spirannulation Reaction: An Umpolung Strategy for Formation of α-Alkylated-α-Hydroxyoxindoles
  作者：Barry M. Trost、Keiichi Hirano

  DOI：10.1021/ol300577y

  日期：2012.5.18

  A highly diastereo- and enantioselective formal [3 + 2] cycloaddition of α,β-unsaturated esters and 3-hydroxyoxindoles catalyzed by a dinuclear zinc-ProPhenol complex is reported. The stereoselective Michael additions of 3-hydroxyoxindoles and the subsequent transesterifications afford spirocyclic δ-lactones.

  据报道，由双核锌-ProPhenol配合物催化的α，β-不饱和酯和3-羟基羟吲哚的高度非对映体和对映体选择性的[3 + 2]环加成反应。3-羟基羟吲哚的立体选择性迈克尔加成和随后的酯交换反应提供螺环δ-内酯。
• Axially dissymmetric binaphthyldiimine chiral salen-type ligands for copper-catalyzed asymmetric aziridination
  作者：Min Shi、Chuan-Jiang Wang、Albert S.C. Chan

  DOI：10.1016/s0957-4166(01)00534-1

  日期：2001.12

  chiral salen-type ligands 1–4 and 7 were prepared from the reaction of (R)-(+)-1,1′-binaphthyl-2,2′-diamine with 2,6-dichlorobenzaldehyde, 2,3-dichlorobenzaldehyde, 3,4-dichlorobenzaldehyde or salicylaldehyde in high yields, respectively. The catalytic asymmetric aziridination of alkenes has been examined using these novel chiral ligands. Excellent enantioselectivity in the aziridination of cinnamates

  轴向不对称的手性Salen型配体1 - 4和7从（的反应制备- [R ）- （+） - 1,1'-联萘-2,2'-二胺与2,6-二氯苯甲醛，2,3-分别以高收率得到二氯苯甲醛，3,4-二氯苯甲醛或水杨醛。使用这些新型手性配体已经研究了烯烃的催化不对称叠氮化。使用C 2对称手性配体1可以实现肉桂酸酯叠氮的出色对映选择性。