5-Chlor-2-hydroxy-zimtsaeure-methylester | 20884-00-8

• 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: 5-Chlor-2-hydroxy-zimtsaeure-methylester
• 英文别名: Methyl 3-(5-chloro-2-hydroxyphenyl)prop-2-enoate
• CAS: 20884-00-8
• 化学式: C₁₀H₉ClO₃
• 分子量: 212.633
• InChiKey: WNOPDBFXHXNUJN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-Chlor-2-hydroxy-zimtsaeure-methylester 生成 6-氯-2H-色烯-2-酮
  参考文献：
  名称：

  Carboxylic esters radical leaving groups: a new and efficient gas-phase synthesis of benzofurans

  摘要：

  邻烯丙基肉桂酸酯的闪速真空热解（FVP）可通过苯氧自由基的环化和随后的羧基酯功能裂解，得到高产率的苯并呋喃；相应苯酚的 FVP 可得到香豆素。

  DOI：

  10.1039/c39930000959
• 作为产物：
  描述：

  4-氯-2-碘苯酚 、 丙烯酸甲酯（MA） 在 silver trifluoroacetate 、 palladium dichloride 作用下， 以70 %的产率得到5-Chlor-2-hydroxy-zimtsaeure-methylester
  参考文献：
  名称：

  Ligand-free Pd-catalyzed highly selective arylation of activated and unactivated alkenes via oxidative and reductive heck coupling

  摘要：

  我们开发了一种无溶剂、温和、高效的 Heck-Mizoroki 反应规程，该规程可在露天超声波辐照下使用一系列基质，具有可预测性和稳健性。

  DOI：

  10.1039/d3ra08186a

文献信息

• Planar Chiral [2.2]Paracyclophane-Based Bisoxazoline Ligands: Design, Synthesis, and Use in Cu-Catalyzed Inter- and Intramolecular Asymmetric O–H Insertion Reactions
  作者：Shinji Kitagaki、Shunsuke Murata、Kisaki Asaoka、Kenta Sugisaka、Chisato Mukai、Naoko Takenaga、Keisuke Yoshida

  DOI：10.1248/cpb.c18-00519

  日期：2018.10.1

  insertion reactions of α-diazo esters. The reactivities and enantioselectivities of Cu complexes of the synthesized bisoxazoline ligands were lower than those of ligands without central chirality. However, planar chiral [2.2]paracyclophane-based bisoxazoline ligands with an inserted benzene spacer that had a sterically demanding isopropyl substituent showed good enantioselectivities in inter- and intramolecular

  合成了直接连接到平面手性[2.2]对环环烷骨架上的中心手性双恶唑啉，并在Cu催化的α-重氮酯的分子间乙醇氢插入反应中将其作为不对称配体进行了评估。合成的双恶唑啉配体的Cu配合物的反应性和对映选择性低于没有中心手性的配体。然而，具有手性要求高的异丙基取代基的带有插入的苯间隔基的平面手性[2.2]对环环烷基双恶唑啉配体在分子间和分子内芳族OH插入反应中没有良好的对映选择性，而没有中心手性。
• Electronically unfavorable addition of electron-deficient olefins to isochromenylium tetrafluoroborates initiated by C-1 O-glycosylation
  作者：Shu-Yan Yu、Zhi-Long Hu、Hao Zhang、Shaozhong Wang、Zhu-Jun Yao

  DOI：10.1016/j.tetlet.2012.03.106

  日期：2012.5

  and electron-deficient olefins have been studied and achieved by assistance of a phenolic hydroxyl group in the olefin substrates, providing the corresponding 2-oxabicyclo[3.3.1]nonane derivatives diastereoselectively in moderate to satisfactory yields. The new methodology is initiated by an intermolecular C-1 O-glycosylation, and completed with an intramolecular Michael addition and an aldol condensation

  已经研究并通过在烯烃底物中的酚羟基的帮助下实现了异氟氰化四氟硼酸酯与缺电子烯烃之间的电子不利反应，并以中等至令人满意的收率选择性地非对映地提供了相应的2-氧杂双环[3.3.1]壬烷衍生物。新的方法是由分子间的C-1 O-糖基化引发的，并以分子内迈克尔加成反应和级联方式的羟醛缩合反应完成。
• Acylation, methylation, and carboxyalkylation of olefins by Group VIII metal derivatives
  作者：Richard F. Heck

  DOI：10.1021/ja01022a034

  日期：1968.9
• An Efficient Large Scale Synthesis of Coumarins by a Dealkylative Boron-Mediated Ring Closure of 3-(Ortho-methoxyaryl)propenoic Esters
  作者：T. Dubuffet、A. Loutz、G. Lavielle

  DOI：10.1080/00397919908086054

  日期：1999.3

  Various substituted coumarins 3 were prepared via a dealkylative boron-mediated ring closure of ortho-methoxycinnamates 2.
• Organocatalyzed Asymmetric Synthesis of Dihydrodibenzofurans Based on a Dienamine Process
  作者：Zi-Yu Wang、Wing-Tak Wong、Dan Yang

  DOI：10.1021/ol402288y

  日期：2013.10.4

  The first organocatalyzed asymmetric method for the synthesis of dihydrodibenzofurans based on a dienamine process has been developed. This two-step protocol works with a broad range of substrates and delivers only the cis-diastereomer in good yield with up to 91% ee. The enantioenriched products have been transformed to highly functionalized and partially hydrogenated dibenzofurans in excellent diastereoselectivities.