1-(2-碘-5-甲氧基苯基)乙酮 | 110718-87-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-(2-碘-5-甲氧基苯基)乙酮
• 英文名称: 1-(2-iodo-5-methoxyphenyl)ethanone
• 英文别名: 2-iodo-5-methoxyacetophenone
• CAS: 110718-87-1
• 化学式: C₉H₉IO₂
• 分子量: 276.074
• InChiKey: GZVPTJZTIXQBFW-UHFFFAOYSA-N

物化性质

• 沸点：
  304.2±32.0 °C(Predicted)
• 密度：
  1.652±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 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：

  1-(2-碘-5-甲氧基苯基)乙酮 在 sodium perborate 、 lithium aluminium tetrahydride 、 正丁基锂 、 四甲基乙二胺 、 碘 、 sodium hydride 、 (-)-diisopinocamphenylborane chloride 作用下， 以 四氢呋喃 为溶剂， 反应 46.5h， 生成 (S)-bis(acetato-O)[2-(1-methoxyethyl)-6-methoxyphenyl]iodine
  参考文献：
  名称：

  New Chiral Hypervalent Iodine Compounds in Asymmetric Synthesis

  摘要：

  The synthesis of new chiral hypervalent iodine compounds 3 and their use in asymmetric oxidative functionalizations are described. The substituents in the chiral moiety and the stereoelectronic properties of the reagents 3, as well as the reaction conditions, have been optimized. Chiral hypervalent iodine compounds 3 have been investigated in the asymmetric dioxytosylation of styrene and in the alpha-oxytosylation of propiophenone as test reactions. X-ray structural analysis of some reagents shows an interaction between the chiral moiety and the iodine resulting in stereoselectivities up to 53% ee in the products.

  DOI：

  10.1021/jo980475x
• 作为产物：
  描述：

  1-(2-氨基-5-甲氧基苯基)-乙酮 在 盐酸 、 potassium iodide 、 sodium nitrite 作用下， 以75%的产率得到1-(2-碘-5-甲氧基苯基)乙酮
  参考文献：
  名称：

  New Chiral Hypervalent Iodine Compounds in Asymmetric Synthesis

  摘要：

  The synthesis of new chiral hypervalent iodine compounds 3 and their use in asymmetric oxidative functionalizations are described. The substituents in the chiral moiety and the stereoelectronic properties of the reagents 3, as well as the reaction conditions, have been optimized. Chiral hypervalent iodine compounds 3 have been investigated in the asymmetric dioxytosylation of styrene and in the alpha-oxytosylation of propiophenone as test reactions. X-ray structural analysis of some reagents shows an interaction between the chiral moiety and the iodine resulting in stereoselectivities up to 53% ee in the products.

  DOI：

  10.1021/jo980475x

文献信息

• Cu(0)/Selectfluor System-Mediated Mild Synthesis of Fluorinated Fluorenones from Nonaromatic Precursors (1,6-Enynes) Involving C–C Single Bond Cleavage
  作者：Jian Zhang、Heng Wang、Shaobo Ren、Wei Zhang、Yunkui Liu

  DOI：10.1021/acs.orglett.5b01110

  日期：2015.6.19

  A novel and facile method for the mild construction of fluorinated fluorenones from nonaromatic precursors (1,6-enynes) mediated by a Cu(0)/Selectfluor system has been successfully achieved. Preliminary mechanistic investigations indicate that the reaction may proceed via an unprecedented annulation/C–C single bond cleavage/fluorination sequence.

  从Cu（0）/ Selectfluor系统介导的非芳香族前体（1,6-炔烃）轻柔地构造氟化芴酮的温和构造的新型，简便方法已成功实现。初步的机理研究表明，该反应可能通过空前的环化/ CC单键裂解/氟化过程进行。
• Palladium-catalyzed <i>ortho</i>-halogen-induced deoxygenative approach of alkyl aryl ketones to 2-vinylbenzoic acids
  作者：Shankar Ram、Ajay Kumar Sharma、Arvind Singh Chauhan、Pralay Das

  DOI：10.1039/d0cc02941f

  日期：——

  polymer chemistry and are key precursors for the synthesis of important bioactive molecules. Herein, an ortho-halogen-induced deoxygenative approach for the generation of 2-vinylbenzoic acids from alkyl aryl ketones by palladium catalysis is discovered and explored. This approach requires no base or stoichiometric additives and can be carried out through a simple one-step process. Furthermore, the present

  2-乙烯基苯甲酸在聚合物化学领域具有广泛的应用，并且是合成重要生物活性分子的关键前体。在这里，一个邻-卤素诱导的脱氧方法，通过钯催化从烷基芳基酮生成2-乙烯基苯甲酸。该方法不需要碱或化学计量的添加剂，可以通过简单的一步过程进行。此外，本反应可扩展至一克规模。市售的碳载钯（5 wt％）用作多相催化剂，显示出极好的可回收性（<5倍），而催化活性没有明显损失。令人满意地，在我们的优化条件下，α烷基取代的2-碘苯乙酮表现出良好的非对映选择性，并且以良好的至优异的产率获得了主要的（E）-2-乙烯基苯甲酸。
• ——
  作者：M. Dellagreca、A. Fiorentino、P. Monaco、G. Pinto、L. Previtera、A. Zarrelli

  DOI：10.1023/a:1005624304413

  日期：——

  mimics of natural compounds with strong antialgal activity, have been synthesized through cross-coupling by zerovalent Ni of 1-(2-iodo-5-methoxy)-phenylethanol or 2-iodo-5-methoxyacetophenone with iodoxylenes. The synthetic compounds had a hydroxyl or a methoxyl group at C-2 and two methyls in the C ring. Assays on the green alga Selenastrum capricornutum showed that all the compounds, except 2-methoxy-5

  9，10-二氢菲和菲是具有强抗藻活性的天然化合物的模拟物，是通过零价Ni与1-（2-碘-5-甲氧基）-苯基乙醇或2-碘-5-甲氧基苯乙酮与零价镍交叉偶联而合成的碘代二甲苯。合成化合物在C-2处具有羟基或甲氧基，并且在C环中具有两个甲基。绿藻硒硒的测定表明，除2-甲氧基-5,7-二甲基菲外，所有化合物均对10（-4）M处的藻类生长产生强烈抑制作用。2-羟基-7,8-二甲基-9， 10-二氢菲和2-甲氧基-5,6-二甲基菲完全抑制了10（-5）M的生长。
• Solvent directed electrophilic iodination and phenylselenenylation of activated alkyl aryl ketones
  作者：Barbara Panunzi、Lucia Rotiroti、Marco Tingoli

  DOI：10.1016/j.tetlet.2003.10.037

  日期：2003.12

  A mixture of molecular iodine and phenyliodine(III) bis(trifluoroacetate) (BTI) in CH3CN (or CH3OH) iodinates the aromatic ring of some activated alkyl aryl ketones. A different outcome results if PhSeSePh is used instead of I2 in the presence of BTI. In CH3CN the aromatic phenylselenenylation is still observed while in CH3OH the formation of α-phenylseleno ketones occurs followed by the conversion

  CH 3 CN（或CH 3 OH）中的分子碘和苯基碘（III）双（三氟乙酸盐）（BTI）的混合物碘化了一些活化的烷基芳基酮的芳环。如果在存在BTI的情况下使用PhSeSePh代替I 2，则会得到不同的结果。在CH 3 CN中，仍然观察到芳族苯基硒烯化，而在CH 3 OH中，发生α-苯基硒酮的形成，然后将这些中间体以中等至良好的产率转化为相应的α，α-二甲氧基羰基化合物。
• A Conjunctive Carboiodination: Indenes by a Double Carbopalladation-Reductive Elimination Domino Process
  作者：Xiaodong Jia、David A. Petrone、Mark Lautens

  DOI：10.1002/anie.201204716

  日期：2012.9.24

  Something gained, nothing lost: A Pd0‐catalyzed domino intermolecular/intramolecular process terminated by carbohalogenation is reported. In this reaction, two new CC bonds, one new CI bond and one five‐membered ring are formed in a single step, and all of the atoms in the starting materials are incorporated into the product (see scheme).

  有所收获，没有任何损失：据报道，Pd 0催化的多米诺骨质分子间/分子内过程因碳卤化作用而终止。在该反应中，一个步骤中形成了两个新的CC键，一个新的CI键和一个五元环，并且原料中的所有原子都掺入了产物中（参见方案）。