methyl (E)-3-(3-chlorophenyl)prop-2-enoate | 24583-84-4

• 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: methyl (E)-3-(3-chlorophenyl)prop-2-enoate
• 英文别名: methyl (E)-3-(3-chlorophenyl)acrylate；(E)-Methyl 3-(3-chlorophenyl)acrylate
• CAS: 24583-84-4
• 化学式: C₁₀H₉ClO₂
• mdl: MFCD02149457
• 分子量: 196.633
• InChiKey: QCCTYRQOMYMCCU-AATRIKPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 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：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 储存条件：
  2-8℃

反应信息

• 作为反应物：
  描述：

  methyl (E)-3-(3-chlorophenyl)prop-2-enoate 在 palladium on activated charcoal lithium aluminium tetrahydride 、 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 3-(3-氯苯基)-1-丙醇
  参考文献：
  名称：

  Synthesis of N-Glyoxyl Prolyl and Pipecolyl Amides and Thioesters and Evaluation of Their In Vitro and In Vivo Nerve Regenerative Effects

  摘要：

  The recent discovery that small molecule ligands for the peptidyl-prolyl isomerase (PPIase) FKBP12 possess powerful neuroprotective and neuroregenerative properties in vitro and in vivo suggests therapeutic utility for such compounds in neurodegenerative disease. The neurotrophic effects of these compounds are independent of the immunosuppressive pathways by which drugs such as FK506 and rapamycin operate. Previous work by ourselves and other groups exploring the structure-activity relationships (SAR) of small molecules that mimic only the FKBP binding domain portion of FK506 has focused on esters of proline and pipecolic acid. We have explored amide and thioester analogues of these earlier structures and found that they too are extremely potent in promoting recovery of lesioned dopaminergic pathways in a mouse model of Parkinson's disease. Several compounds were shown to be highly effective upon oral administration after lesioning of the dopaminergic pathway, providing further evidence of the potential clinical utility of a variety of structural classes of FKBP12 ligands.

  DOI：

  10.1021/jm010556c
• 作为产物：
  描述：

  三苯胂 在 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 反应 0.75h， 生成 methyl (E)-3-(3-chlorophenyl)prop-2-enoate
  参考文献：
  名称：

  通过由三苯ar介导的维蒂希反应合成烯烃。

  摘要：

  描述了用于合成烯烃的a介导的Wittig反应。在活化的烷基溴的存在下将三苯基ar加热30分钟后，所得ar盐在室温下仅用5分钟即可与醛缩合，以高收率得到烯烃。芳族，杂芳族和烷基醛都是适合该方法的底物。

  DOI：

  10.1016/j.tetlet.2017.02.051

文献信息

• Mizoroki–Heck Reaction of Unstrained Aryl Ketones via Ligand-Promoted C–C Bond Olefination
  作者：Mei-Ling Wang、Hui Xu、Han-Yuan Li、Biao Ma、Zhen-Yu Wang、Xing Wang、Hui-Xiong Dai

  DOI：10.1021/acs.orglett.1c00296

  日期：2021.3.19

  Mizoroki–Heck reaction of unstrained aryl ketone with acrylate/styrene is accomplished via palladium-catalyzed ligand-promoted C–C bond cleavage. Various (hetero)aryl ketones are compatible in the reaction, affording the alkene product in good to excellent yields. Further applications in the late-stage olefination of some drugs, natural products, and fragrance-derived aryl ketones demonstrate the synthetic utility

  未应变的芳基酮与丙烯酸酯/苯乙烯的Mizoroki-Heck反应是通过钯催化的配体促进的C-C键裂解实现的。各种（杂）芳基酮在反应中是相容的，从而以良好至优异的产率提供了烯烃产物。在某些药物，天然产物和香料衍生的芳基酮的后期烯烃聚合中的进一步应用证明了该方案的合成效用。通过采用酮作为导向基团和离去基团二者，1,2- bifunctionalization经由顺序实现邻-C-H的烷基化/本位-Heck烯。
• Phosphetane Oxides as Redox Cycling Catalysts in the Catalytic Wittig Reaction at Room Temperature
  作者：Lars Longwitz、Anke Spannenberg、Thomas Werner

  DOI：10.1021/acscatal.9b02456

  日期：2019.10.4

  renewable solvent. The intermediates of the Wittig reaction were analyzed by 31P NMR spectroscopy, and in situ NMR experiments confirmed phosphane oxide as the resting state of the catalyst. Further kinetic investigations revealed a striking influence of the base on the rate of phosphane oxide reduction.

  近来，磷氧化还原循环对于最初要求使用化学计量的磷试剂的许多转化已变得非常重要。尽管这些方法具有多种优势，但催化剂负载量高（≥10 mol％）和苛刻的反应条件（T≥100°C）通常会限制其通用性和适用性。在本文中，我们报道了不同取代的氧化膦作为有效的Wittig反应催化剂。磷脂骨架易于修饰，并且可以通过简单的两步合成获得多种催化剂。Wittig反应中的活性大大超过了先前报道的基于磷杂环戊烷的催化剂，并且即使在室温下，该反应也可以以低至1.0 mol％的催化剂负载量进行。此外，在这些温和条件下不再需要布朗斯台德酸添加剂即可实现高收率。甲基取代的氧化膦用于合成25种不同的烯烃，收率高达97％。该方法具有良好的官能团耐受性，该反应可以从烷基氯化物，溴化物，或碘化物。另外，可以在使用2-MeTHF作为可再生溶剂的催化Wittig反应中使用聚（甲基氢硅氧烷）作为末端还原剂。Wittig反应的中间体通过31
• Ozonolysis of some 8-alkoxyquinolines, and synthesis of a precursor to the non-sedating antihistamine Claritin
  作者：Mathias C. Eichler、David H. Grayson

  DOI：10.3998/ark.5550190.p008.843

  日期：——

  near-ambient conditions. The compou nds can be utilized as intermediates for syntheses of the tricyclic ketone 8-chloro-6,11-dih y ro-5H-benzo[5,6]cyclohepta[1,2b]pyridin11-one, a precursor to the important non-sedating a ntihistamine Claritin.

  3-甲酰基-2-甲氧基羰基吡啶和3-甲酰基吡啶-2-羧酸异丙酯均通过在接近环境条件下8-甲氧基或8-异丙氧基喹啉的臭氧分解而在一个步骤中有效地获得。该化合物可用作合成三环酮 8-chloro-6,11-dih y ro-5H-benzo[5,6]cyclohepta[1,2b]pyridin11-one 的中间体，这是重要的非- 镇静抗组胺药 Claritin。
• A Deacetylation-Diazotation-Coupling Sequence: Palladium- Catalyzed CC Bond Formation with Acetanilides as Formal Leaving Groups
  作者：Bernd Schmidt、René Berger

  DOI：10.1002/adsc.201200929

  日期：2013.2.1

  Acetanilides can be deacetylated and diazotized in situ, and subsequently used in Pd-catalyzed coupling reactions without isolation of the diazonium intermediate. Heck reactions, Suzuki cross-coupling reactions, and a Pd-catalyzed [2+2+1] cycloaddition have been investigated as terminating CC bond-forming steps of this one-flask sequence. The sequence does not require the exchange of solvents or removal

  乙酰苯胺可以原位脱乙酰化和重氮化，然后在不分离重氮中间体的情况下用于Pd催化的偶联反应中。Heck反应，Suzuki交叉偶联反应和Pd催化的[2 + 2 + 1]环加成反应已作为该一瓶序列的终止CC键形成步骤进行了研究。该顺序不需要在各个步骤之间交换溶剂或除去副产物，而是在适当的时候通过添加试剂和催化剂来进行。
• Selective Palladium-Catalyzed Carbonylation of Alkynes: An Atom-Economic Synthesis of 1,4-Dicarboxylic Acid Diesters
  作者：Jiawang Liu、Kaiwu Dong、Robert Franke、Helfried Neumann、Ralf Jackstell、Matthias Beller

  DOI：10.1021/jacs.8b05852

  日期：2018.8.15

  dialkoxycarbonylation of various aromatic and aliphatic alkynes affording a wide range of 1,4-dicarboxylic acid diesters in high yields and selectivities. Kinetic studies suggest the generation of 1,4-dicarboxylic acid diesters via cascade hydroesterification of the corresponding alkynes. Based on these investigations, the chemo- and regioselectivities of alkyne carbonylations can be controlled as shown by switching

  首次设计合成了一类带有吡啶取代基的新型二膦配体。所得的 L1 钯配合物允许对各种芳香族和脂肪族炔烃进行化学和区域选择性二烷氧基羰基化，以高产率和选择性提供范围广泛的 1,4-二羧酸二酯。动力学研究表明通过相应炔烃的级联加氢酯化生成 1,4-二羧酸二酯。基于这些研究，炔烃羰基化的化学和区域选择性可以通过将配体从 L1 切换到 L3 或 L9 以得到 α,β-不饱和酯来控制。