2-(2-碘苯基)乙酸乙酯 | 90794-29-9

• 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: 2-(2-碘苯基)乙酸乙酯
• 中文别名: 2-碘苯乙酸乙酯；邻碘苯乙酸乙酯
• 英文名称: ethyl (2-iodophenyl)acetate
• 英文别名: ethyl 2-(2-iodophenyl)acetate
• CAS: 90794-29-9
• 化学式: C₁₀H₁₁IO₂
• 分子量: 290.101
• InChiKey: XBKDPADMOCFNED-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  存储条件：2-8°C，避免光照，密封保存。

反应信息

• 作为反应物：
  描述：

  2-(2-碘苯基)乙酸乙酯 在 四丁基氯化铵 、 potassium acetate 、 palladium diacetate 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 60.0h， 生成 diethyl 2-tert-butyl-3-methyl-1H-indene-1,1-dicarboxylate
  参考文献：
  名称：

  Synthesis of Indenes by the Palladium-Catalyzed Carboannulation of Internal Alkynes

  摘要：

  [GRAPHICS]A number of highly substituted indenes have been prepared in good yields by treating functionally substituted aryl halides with various internal alkynes in the presence of a palladium catalyst. The reaction is believed to proceed by regioselective arylpalladation of the alkyne and subsequent nucleophilic displacement of the palladium in the resulting vinylpalladium intermediate.

  DOI：

  10.1021/ol051907a
• 作为产物：
  描述：

  2-碘苯基乙腈 在 盐酸 作用下， 反应 48.0h， 生成 2-(2-碘苯基)乙酸乙酯
  参考文献：
  名称：

  4,6-O-[1-Cyano-2-(2-iodophenyl)ethylidene] Acetals. Improved Second-Generation Acetals for the Stereoselective Formation of β-d-Mannopyranosides and Regioselective Reductive Radical Fragmentation to β-d-Rhamnopyranosides. Scope and Limitations

  摘要：

  The [1-cyano-2-(2-iodophenyl)]ethylidene group is introduced as an acetal-protecting group for carbohydrate thioglycoside donors. The group is easily introduced under mild conditions, over short reaction times, and in the presence of a wide variety of other protecting groups by the reaction of the 4,6-diol with triethyl (2-iodophenyl)orthoacetate and camphorsulfonic acid, followed by trimethylsilyl cyanide and boron trifluoride etherate. The new protecting group conveys strong beta-selectivity with thiomannoside donors and undergoes a tin-mediated radical fragmentation to provide high yields of the synthetically challenging beta-rhamnopyranosides. The method is also applicable to the glucopyranosides when high beta-selectivity is observed in the coupling reaction and alpha-quinovosides are formed selectively in the radical fragmentation step. In the galactopyranoside series, beta-glycosides are formed selectively on coupling to donors protected by the new system, but the radical fragmentation is unselective and gives mixtures of the 4- and 6-deoxy products. Variable-temperature NMR studies for the glycosylation step, which helped define an optimal protocol, are described.

  DOI：

  10.1021/jo0526688

文献信息

• Synthesis of Indene Derivatives via Electrophilic Cyclization
  作者：Zulfiqar Ali Khan、Thomas Wirth

  DOI：10.1021/ol8024956

  日期：2009.1.1

  iodonium-promoted 5-endo-dig carbocyclization of 2-substituted ethynylmalonates. Various 2-substituted ethynylmalonates bearing aryl-, alkyl- and ether-protected propargyl alcohols were successfully converted to cyclized products. Their use in subsequent reactions as substrate and catalyst was investigated.

  3-碘1H -茚衍生物是通过碘鎓促进的5-合成内切-挖2-取代ethynylmalonates的carbocyclization。带有芳基，烷基和醚保护的炔丙醇的各种2-取代的乙炔基丙二酸酯已成功转化为环化产物。研究了它们在后续反应中作为底物和催化剂的用途。
• Electrochemical‐Induced Ring Transformation of Cyclic α‐( <i>ortho</i> ‐Iodophenyl)‐β‐oxoesters
  作者：Julia Strehl、Christoph Kahrs、Thomas Müller、Gerhard Hilt、Jens Christoffers

  DOI：10.1002/chem.201905570

  日期：2020.3.12

  cycloalkanone carboxylic esters. The reaction sequence started by electrochemical reduction of the iodoarene moiety. In a mechanistic rationale, the resulting carbanionic species was adding to the carbonyl group under formation of a strained, tricyclic benzocyclobutene intermediate, which underwent carbon-carbon bond cleavage and rearrangement of the carbon skeleton by retro-aldol reaction. The scope of

  环状α-（邻碘苯基）-β-氧酸酯经扩环转化而得到苯并环化的环烷酮羧酸酯。反应序列通过碘代芳烃部分的电化学还原开始。从机理上讲，生成的碳负离子物质是在形成应变的三环苯并环丁烯中间体的情况下加到羰基上的，该中间体经历了碳-碳键的断裂和碳骨架通过逆醛醇缩合反应的重排。通过转化具有不同环尺寸的环状氧代酯以中等至良好的产率产生苯并环庚酮，-壬酮和-癸酮衍生物来研究反应序列的范围。此外，无环起始原料和在碘苯基环上带有其他取代基的环状化合物已进入该反应顺序。该转化的起始原料可通过将β-氧代酸酯与苯基碘代双（三氟乙酸酯）转化而直接获得。
• Synthesis of Indenes by the Transition Metal-Mediated Carboannulation of Alkynes
  作者：Daohua Zhang、Zhijian Liu、Eul K. Yum、Richard C. Larock

  DOI：10.1021/jo0620563

  日期：2007.1.1

  The synthesis of highly substituted indenes has been achieved by three different transition metal-mediated methods. The first method involves the palladium-catalyzed carboannulation of internal alkynes. The second method utilizes a two-step approach, which involves first the palladium/copper-catalyzed cross-coupling of terminal alkynes with appropriately functionalized aryl halides, followed by copper-catalyzed

  通过三种不同的过渡金属介导的方法可以实现高度取代的茚的合成。第一种方法涉及内部炔烃的钯催化碳环化反应。第二种方法采用两步法，其中首先涉及末端炔烃与适当官能化的芳基卤化物的钯/铜催化交叉偶联，然后进行铜催化的分子内环化。第三种方法涉及在第二种方法的第一步中形成的芳基炔烃的分子间钯催化的芳基化。
• [EN] 1-HETEROCYCLYL-1,5-DIHYDRO-PYRAZOLO[3,4-D] PYRIMIDIN-4-ONE DERIVATIVES AND THEIR USE AS PDE9A MODULATORS<br/>[FR] DÉRIVÉS DE 1-HÉTÉROCYCLYL-1,5-DIHYDRO-PYRAZOLO[3,4-D]PYRIMIDIN-4-ONE ET LEURS UTILISATIONS À TITRE DE MODULATEURS DE PDE9A
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2009121919A1

  公开（公告）日：2009-10-08

  The invention relates to novel 1,6-disubstituted pyrazolopyrimidinones, Formula (I) with Hc is a mono-, bi- or tricyclic heterocyclyl group, the ring members of which are carbon atoms and at least 1, preferably 1, 2 or 3, heteroatom(s), which are selected from the group of nitrogen, oxygen and sulphur, which is in the form of -S(O)r - with r being 0, 1 or 2, and - said heterocyclyl group is or comprises 1 non-aromatic, saturated, or partly unsaturated monocyclic ring which comprises at least 1 heteroatom as ring member and - said heterocyclyl group is bound to the scaffold by said 1 non- aromatic, saturated, or partly unsaturated monocyclic ring which comprises at least 1 heteroatom as ring member. According to one aspect of the invention the new compounds are for the manufacture of medicaments, in particular medicaments for the treatment of conditions concerning deficits in perception, concentration, learning or memory. The new compounds are also for the manufacture of medicaments for the treatment of Alzheimer's disease.

  该发明涉及新型1,6-二取代吡唑吡嘧啶酮，化学式（I），其中Hc是一个单环、双环或三环杂环基团，其环成员为碳原子和至少1个，优选1个、2个或3个来自氮、氧和硫的杂原子，其以-S(O)r-的形式存在，其中r为0、1或2，所述杂环基团是或包括1个非芳香、饱和或部分不饱和的单环环，其中至少包含1个杂原子作为环成员，所述杂环基团通过所述至少包含1个杂原子作为环成员的非芳香、饱和或部分不饱和的单环环与支架相结合。根据该发明的一个方面，新化合物用于制造药物，特别是用于治疗感知、注意力、学习或记忆缺陷相关疾病的药物。新化合物还用于制造治疗阿尔茨海默病的药物。
• Synthesis of Ring-Fused Oxazolo- and Pyrazoloisoquinolinones by a One-Pot Pd-Catalyzed Carboxamidation and Aldol-Type Condensation Cascade Process
  作者：Gagan Chouhan、Howard Alper

  DOI：10.1021/jo9010574

  日期：2009.8.21

  three-component cascade process is described for the synthesis of ring-fused oxazolo- and pyrazoloisoquinolinones by a one-pot carboxamidation/aldol-type condensation reaction. The cascade process involves Pd-catalyzed carboxamidation of an aryl halide/active methylene compound with oxazolidinone or pyrazolidinone, and subsequent intramolecular base-catalyzed cyclization/dehydration through an aldol-type

  描述了通过单锅羧酰胺化/醛醇缩合反应合成环稠合的恶唑啉和吡唑异喹啉酮的三组分级联方法。级联过程涉及芳基卤化物/活性亚甲基化合物与恶唑烷酮或吡唑烷酮的钯催化羧酰胺化，以及随后的分子内碱催化的醛醇缩合环化/脱水，以产生环稠合的恶唑啉代和吡唑并异喹啉酮。这种方法为这些重要的含氮杂环类化合物提供了一种简单的一步方法，并且可以耐受各种官能团，包括酯，腈，甲氧基和卤化物。