methyl 3-iodo-4-((2-methylallyl)oxy)benzoate | 1104641-58-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 3-iodo-4-((2-methylallyl)oxy)benzoate
• 英文别名: 3-Iodo-4-(2-methyl-allyloxy)-benzoic acid methyl ester；methyl 3-iodo-4-(2-methylprop-2-enoxy)benzoate
• CAS: 1104641-58-8
• 化学式: C₁₂H₁₃IO₃
• 分子量: 332.138
• InChiKey: HLFLPAKNZBRZIE-UHFFFAOYSA-N

物化性质

• 熔点：
  51-52 °C
• 沸点：
  376.3±37.0 °C(Predicted)
• 密度：
  1.524±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  16
• 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：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 3-iodo-4-((2-methylallyl)oxy)benzoate 在 Pd(Q-Phos)₂ 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以92%的产率得到3-iodomethyl-3-methyl-2,3-dihydrobenzofuran-5-carboxylic acid methyl ester
  参考文献：
  名称：

  Palladium-Catalyzed Carboiodination of Alkenes: Carbon−Carbon Bond Formation with Retention of Reactive Functionality

  摘要：

  We report a palladium-catalyzed carbon carbon bond-forming reaction between aryl iodides and alkenes. In contrast to traditional cross-coupling reactions, two new bonds are formed, and all of the atoms in the starting materials are incorporated into the product. The use of a palladium catalyst with bulky phosphine ligands is found to be crucial for reactivity.

  DOI：

  10.1021/ja110377q
• 作为产物：
  描述：

  4-羟基-3-碘苯甲酸 在 硫酸 、 potassium carbonate 作用下， 以 丁酮 为溶剂， 反应 24.0h， 生成 methyl 3-iodo-4-((2-methylallyl)oxy)benzoate
  参考文献：
  名称：

  Heterocyclic modulators of cannabinoid receptors

  摘要：

  呈现了调节大麻素受体的杂环化合物。本文还描述了含有这些化合物的药物组合物、使用这些化合物作为大麻素受体调节剂的方法以及合成这些化合物的过程。

  公开号：

  US09339486B2

文献信息

• Palladium-Catalyzed Three-Component Carbocarbonation of Arynes: Expeditious Synthesis of <i>o</i>-Alkylated Arylacrylates and Stilbenes
  作者：Tuanli Yao、Jiazhe Hui、Tao Liu、Tao Li

  DOI：10.1021/acs.joc.0c02994

  日期：2021.4.16

  A palladium-catalyzed multicomponent reaction involving olefin-tethered aryl iodides, arynes, and electrophilic alkenes has been developed for straightforward synthesis of o-alkylated arylacrylates and stilbenes through tandem intramolecular Heck cyclization/aryne dicarbofunctionalization.

  已经开发了涉及烯烃系链的芳基碘化物，芳烃和亲电烯烃的钯催化的多组分反应，用于通过串联的分子内Heck环化/芳烃二碳官能化直接合成邻烷基化的芳基丙烯酸酯和对苯二甲酸酯。
• Ligand-Controlled Palladium-Catalyzed Chemoselective Multicomponent Reaction of Olefin-Tethered Aryl Halides, Isocyanides, and Carboxylic Acids: Diversified Synthesis of Imides
  作者：Tuanli Yao、Bo Wang、Dan He、Xiaofei Zhang、Xiang Li、Ran Fang

  DOI：10.1021/acs.orglett.0c02297

  日期：2020.9.4

  ligand-controlled chemoselective synthesis of imides has been achieved. An orthogonal set of conditions has been developed for multicomponent reaction of various olefin-tethered aryl iodides, isocyanides, and carboxylic acids. Alkylimides (“cyclization on” products) via arylimidation of tethered unactivated alkenes and aryl imides (“cyclization off” products) via direct imidation of aryl iodides were

  已经实现了钯的第一催化，配体控制的酰亚胺的化学选择性合成。已经开发出一套正交的条件，用于各种烯烃连接的芳基碘化物，异氰酸酯和羧酸的多组分反应。通过芳基碘化物的直接酰亚胺化，通过束缚的未活化烯烃的芳基酰亚胺（“环化”产物）和芳基酰亚胺（“环化”产物）的芳基化以良好或优异的收率获得了良好或优异的选择性。进行计算研究以深入了解所观察到的高化学选择性的起源。
• Efficient assembly of ynones <i>via</i> palladium-catalyzed sequential carbonylation/alkynylation
  作者：Miao Hu、Yang Gao、Wanqing Wu、Jianxiao Li、Chunsheng Li、Hao Zhang、Huanfeng Jiang

  DOI：10.1039/c8ob02092b

  日期：——

  Based on the intramolecular Heck-type reaction, a convenient and efficient strategy to construct functionalized ynones by a palladium-catalyzed cascade annulation reaction has been developed. This reaction possesses good functional group compatibility, a broad substrate scope, and high atom- and step-economy. Furthermore, this approach could also be extended to direct alkynylation that gave another

  基于分子内的Heck型反应，开发了一种方便有效的策略，通过钯催化的级联环化反应来构建功能化的炔酮。该反应具有良好的官能团相容性，广泛的底物范围以及较高的原子经济性和台阶经济性。此外，该方法还可以扩展到直接炔基化，这提供了另一种合成二氢苯并呋喃的途径。
• Palladium-Catalyzed Cascade Carbopalladation/Phenol Dearomatization Reaction: Construction of Diversely Functionalized Spirocarbocyclic Scaffolds
  作者：Xin-Xing Wu、Anjia Liu、Mou Mou、Hengfan Chen、Shufeng Chen

  DOI：10.1021/acs.joc.8b02363

  日期：2018.11.16

  A novel palladium-catalyzed cascade carbopalladation/phenol dearomatization reaction has been achieved. The process provides a variety of indolone-, dihydrobenzofuran-, dihydrobenzopyran- and hydroquinoline-containing spirofused molecules bearing two quaternary centers in moderate to good yields. The potential synthetic utility of this method is demonstrated by a gram-scale experiment and further transformations

  已经实现了新颖的钯催化的级联碳钯/苯酚脱芳香化反应。该方法以中等至良好的产率提供了带有两个四级中心的各种含吲哚酮，二氢苯并呋喃，二氢苯并吡喃和氢喹啉的螺合分子。通过克规模的实验和进一步的转化证明了该方法的潜在合成效用。
• Pd-Catalyzed Sequential Formation of C–C Bonds: A New Strategy for the Synthesis of (<i>E</i>)-α,β-Unsaturated Carbonyl Compounds from Sulfoxonium Ylides and 1-Iodo-2-((2-methylallyl)oxy)benzene Compounds
  作者：Miao Hu、Ziying Wu、Biao Yao、Jianxiao Li、Wanqing Wu、Huanfeng Jiang

  DOI：10.1021/acs.joc.1c01119

  日期：2021.9.3

  α,β-Unsaturated carbonyl compounds are significant moieties in many biological molecules and have attracted considerable attention in organic synthetic chemistry. A Pd-catalyzed cascade cyclization for the synthesis of (E)-α,β-unsaturated carbonyl compounds with the sequential formation of C–C bonds was developed. This method offers high efficiency, good functional group tolerance, and moderate to

  α,β-不饱和羰基化合物是许多生物分子中的重要组成部分，在有机合成化学中引起了相当大的关注。开发了 Pd 催化的级联环化反应，用于合成 ( E )-α,β-不饱和羰基化合物，并依次形成 C-C 键。该方法效率高、官能团耐受性好、产率中等至极好，通常显示出高立体选择性。