(E)-4-(2-溴苯基)-2-丁烯酸乙酯 | 452055-99-1

• 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: (E)-4-(2-溴苯基)-2-丁烯酸乙酯
• 英文名称: ethyl (E)-4-(2-bromophenyl)-2-butenoate
• 英文别名: (E)-4-(2-Bromophenyl)-2-butenoic acid ethyl ester；ethyl (E)-4-(2-bromophenyl)but-2-enoate
• CAS: 452055-99-1
• 化学式: C₁₂H₁₃BrO₂
• 分子量: 269.138
• InChiKey: BSCTVRNJMRNDNN-WEVVVXLNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  copper(l) cyanide 、 (E)-4-(2-溴苯基)-2-丁烯酸乙酯 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以85%的产率得到1-aminonaphthalene-2-carboxylic acid ethyl ester
  参考文献：
  名称：

  CuCN-Mediated Cascade Cyclization of 4-(2-Bromophenyl)-2-butenoates: A High-Yield Synthesis of Substituted Naphthalene Amino Esters

  摘要：

  A new method of CuCN-mediated one-pot cyclization of 4-(2-bromophenyl)-2-butenoates leading to efficient synthesis of substituted naphthalene amino esters including phenanthrene aromatic structural units is described. Deuterium labeling studies establish that this one-pot cascade cyclization proceeds through isomerization of olefin, intramolecular C-C bond cyclization, and aromatization as the key intermediates, all occurring in a single step.

  DOI：

  10.1021/jo400244h
• 作为产物：
  描述：

  1-bromo-2-(2-methoxyvinyl)benzene 在 盐酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 5.0h， 生成 (E)-4-(2-溴苯基)-2-丁烯酸乙酯
  参考文献：
  名称：

  CuCN-Mediated Cascade Cyclization of 4-(2-Bromophenyl)-2-butenoates: A High-Yield Synthesis of Substituted Naphthalene Amino Esters

  摘要：

  A new method of CuCN-mediated one-pot cyclization of 4-(2-bromophenyl)-2-butenoates leading to efficient synthesis of substituted naphthalene amino esters including phenanthrene aromatic structural units is described. Deuterium labeling studies establish that this one-pot cascade cyclization proceeds through isomerization of olefin, intramolecular C-C bond cyclization, and aromatization as the key intermediates, all occurring in a single step.

  DOI：

  10.1021/jo400244h

文献信息

• Synthesis of Substituted Naphthalenes and Carbazoles by the Palladium-Catalyzed Annulation of Internal Alkynes
  作者：Qinhua Huang、Richard C. Larock

  DOI：10.1021/jo034449x

  日期：2003.9.1

  An efficient synthesis of highly substituted naphthalenes has been developed by the palladium-catalyzed annulation of a variety of internal alkynes, in which two new carbon-carbon bonds are formed in a single step under relatively mild reaction conditions. This method has also been used to synthesize carbazoles, although a higher reaction temperature is necessary. The process involves arylpalladation

  通过钯催化的各种内部炔烃的环化反应，已开发出高效取代的萘的有效合成方法，其中，在相对温和的反应条件下，一个步骤即可形成两个新的碳-碳键。尽管需要更高的反应温度，但是该方法也已经用于合成咔唑。该方法涉及炔烃的芳基palladation，随后是分子内的Heck烯烃化和双键异构化。该方法可容纳各种官能团，并以良好或优异的收率提供预期的高度取代的萘和咔唑。
• A General and Highly Selective Chelate-Controlled Intermolecular Oxidative Heck Reaction
  作者：Jared H. Delcamp、Alexandria P. Brucks、M. Christina White

  DOI：10.1021/ja804120r

  日期：2008.8.27

  chelate-controlled intermolecular oxidative Heck reaction is reported that proceeds with a wide range of nonresonance stabilized alpha-olefin substrates and organoboron reagents to afford internal olefin products in good yields and outstanding regio- and E: Z stereoselectivities. Pd-H isomerization, common in many Heck reactions, is not observed under these mild, oxidative conditions. This is evidenced

  据报道，一种新型螯合物控制的分子间氧化 Heck 反应与各种非共振稳定的 α-烯烃底物和有机硼试剂一起进行，以良好的收率和出色的区域和 E:Z 立体选择性提供内烯烃产品。在许多 Heck 反应中常见的 Pd-H 异构化在这些温和的氧化条件下未观察到。这可以通过出色的 E:Z 选择性（在所有检查的情况下 >20:1）、近端立体中心的光学纯度没有侵蚀以及对未受保护的醇的耐受性来证明。值得注意的是，单一金属/配体组合，Pd/双-亚砜配合物 1，在广泛的偶联伙伴上催化该反应。鉴于高选择性和广泛的范围，
• Synthesis of Substituted Naphthalenes by the Palladium-Catalyzed Annulation of Internal Alkynes
  作者：Qinhua Huang、Richard C. Larock

  DOI：10.1021/ol026128y

  日期：2002.7.1

  [reaction: see text] A variety of substituted naphthalenes have been prepared by the palladium-catalyzed carboannulation of internal alkynes. This method (1) forms two new carbon-carbon bonds in a single step, (2) accommodates a variety of functional groups, and (3) affords excellent yields of highly substituted naphthalenes.

  [反应：见正文]通过钯催化内部炔烃的碳环化反应，已经制备了各种取代的萘。该方法（1）在一个步骤中形成两个新的碳-碳键；（2）容纳各种官能团；（3）提供高产率的高度取代的萘。
• PYRROLIDINE DERIVATIVES USEFUL AS BACE INHIBITORS
  申请人：Rogel Olivier

  公开号：US20090247577A1

  公开（公告）日：2009-10-01

  Novel 3-mono-, 3,4-di- and 3,4,4,-tri-substituted pyrrolidine compounds, these compounds for use in the diagnostic and therapeutic treatment of a warm-blooded animal, especially for the treatment of a disease (disorder) that depends on the activity of beta-secretase and/or the generation of beta-amyloid and the subsequent aggregation into oligomers and fibrils; the use of a compound of that class for the preparation of a pharmaceutical formulation for the treatment of a disease that depends on the activity of beta-secretase and/or the generation of beta-amyloid and the subsequent aggregation into oligomers and fibrils; pharmaceutical formulations comprising a said substituted pyrrolidine compound, and/or a method of treatment comprising administering a said substituted pyrrolidine compound. The substituted pyrrolidine compounds are especially of the formula I, wherein the substituents are as defined in the specification.

  小说3-单取代、3,4-双取代和3,4,4-三取代吡咯烷化合物，这些化合物用于诊断和治疗温血动物，特别是用于治疗依赖于β-分泌酶活性和/或β-淀粉样蛋白生成及其后续寡聚体和纤维聚集的疾病（紊乱）；该类化合物的使用用于制备用于治疗依赖于β-分泌酶活性和/或β-淀粉样蛋白生成及其后续寡聚体和纤维聚集的疾病的药物配方；包括所述取代的吡咯烷化合物的药物配方和/或包括给予该取代的吡咯烷化合物的治疗方法。所述取代的吡咯烷化合物特别是公式I的，其中取代基如规范中所定义。
• Cu-Mediated Annulation for the Production of 1-Amino-2-Naphthalenecarboxylic Acid Derivatives
  申请人：Council of Scientific & Industrial Research

  公开号：US20150011781A1

  公开（公告）日：2015-01-08

  Invention provides a cheaper and practical protocol for the construction of a wide variety of 1-Amino-2-naphthalene-carboxylic acid derivatives and their structural analogues that proceeds with high yields in a single step via intramolecular cascade cyano ene reaction.

  该发明提供了一种更便宜、实用的方案，用于构建各种1-氨基-2-萘甲酸衍生物及其结构类似物，通过分子内级联氰基烯反应一步高产得到。