5-(2-iodophenyl)-2-pentanone | 501346-70-9

• 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: 5-(2-iodophenyl)-2-pentanone
• 英文别名: 5-(2-iodophenyl)pentan-2-one
• CAS: 501346-70-9
• 化学式: C₁₁H₁₃IO
• 分子量: 288.128
• InChiKey: TXQWDOAYRXEMFH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-(2-iodophenyl)-2-pentanone 在 silver orthophosphate 、 2-羟基-3,5-二硝基吡啶 、 六氟异丙醇 、 palladium diacetate 、 聚甘氨酸 、 三氟乙酸 作用下， 反应 24.0h， 以41%的产率得到1-(bicyclo[4.2.0]octa-1,3,5-trien-7-yl)propan-2-one
  参考文献：
  名称：

  Pd(II)-催化β-亚甲基选择性C(sp3)-H芳基化与瞬态导向基团合成苯并环丁烯

  摘要：

  亚甲基选择性 C-H 官能化是 Pd(II) 催化领域仍有待解决的重大障碍。我们报告了通过酮的亚甲基选择性 C(sp 3 )-H 芳基化合成苯并环丁烯的 Pd(II) 催化。该反应利用甘氨酸作为瞬态导向基团和 2-吡啶酮配体，这可以通过在协同金属化-去质子化过程中与底物形成紧密的分子结合来控制亚甲基的选择性。该反应被证明对分子内亚甲基 C(sp 3 )-H 芳基化具有高度选择性，因此能够实现连续的 C(sp 3 )-H 官能化。

  DOI：

  10.1021/jacs.1c09368
• 作为产物：
  描述：

  2-acetyl-4-(2-iodophenyl)butyrate 在 sodium hydroxide 、 硫酸 作用下， 以 水 为溶剂， 反应 29.0h， 以0.44 g的产率得到5-(2-iodophenyl)-2-pentanone
  参考文献：
  名称：

  Intramolecular Pd-Mediated Processes of Amino-Tethered Aryl Halides and Ketones:  Insight into the Ketone α-Arylation and Carbonyl-Addition Dichotomy. A New Class of Four-Membered Azapalladacycles

  摘要：

  An exploration of the scope and limitations of Pd(0)-catalyzed intramolecular coupling reactions of amino-tethered aryl halides and ketones has been conducted. Two different and competitive reaction pathways starting from omega-(2-haloanilino) alkanones, enolate arylation and addition to the carbonyl group, have been observed, while (omega-(2-halobenzylamino) alkanones exclusively underwent the enolate arylation process. The dichotomy between ketone alpha-arylation and carbonyl-addition in the reactions of omega-(2-haloanilino) alkanones has been rationalized by the intermediacy of unprecedented four-membered azapalladacycles, from which X-ray data and chemical behavior are reported.

  DOI：

  10.1021/ja029114w

文献信息

• [EN] TETRAHYDRO-NAPHTHALENE DERIVATIVES AS GLUCOCORTICOID RECEPTOR MODULATORS<br/>[FR] DÉRIVÉS DE TÉTRAHYDRONAPHTHALÈNE SERVANT DE MODULATEURS DU RÉCEPTEUR DES GLUCOCORTICOÏDES
  申请人：GLAXO GROUP LTD

  公开号：WO2006015870A1

  公开（公告）日：2006-02-16

  The present invention is directed to compounds of formula (I): wherein R represents a methyl or an ethyl group X represents N, C-H or C-CH3 when X represents C-H or C-CH3, Y represents N when X represents N, Y represents C-H and physiologically functional derivatives thereof, pharmaceutical compositions comprising the compounds, the use of the compounds for the manufacture of medicaments particularly for the treatment of inflammatory and/or allergic conditions, processes for the preparation of the compounds, and chemical intermediates in the processes for the manufacture of the compounds.

  本发明涉及以下式（I）的化合物：其中R代表甲基或乙基基团，X代表N、C-H或C-CH3，当X代表C-H或C- 时，Y代表N，当X代表N时，Y代表C-H以及其生理功能衍生物，包括该化合物的药物组合物，该化合物用于制备药物，特别用于治疗炎症和/或过敏症状，该化合物的制备方法以及用于制备该化合物的化学中间体。
• Chromium(II)-catalyzed enantioselective arylation of ketones
  作者：Gang Wang、Shutao Sun、Ying Mao、Zhiyu Xie、Lei Liu

  DOI：10.3762/bjoc.12.275

  日期：——

  The chromium-catalyzed enantioselective addition of carbo halides to carbonyl compounds is an important transformation in organic synthesis. However, the corresponding catalytic enantioselective arylation of ketones has not been reported to date. Herein, we report the first Cr-catalyzed enantioselective addition of aryl halides to both arylaliphatic and aliphatic ketones with high enantioselectivity in an intramolecular version, providing facile access to enantiopure tetrahydronaphthalen-1-ols and 2,3-dihydro-1H-inden-1-ols containing a tertiary alcohol.

  铬催化的卤代烃对羰基化合物的不对称加成是有机合成中的重要转化。然而，到目前为止，尚未报道酮的相应催化不对称芳基化。在这里，我们报告了第一个铬催化的对芳基卤代烃对芳基脂肪族和脂肪族酮的不对称加成，具有高对映选择性的分子内版本，提供了易于获得的对映纯四氢萘-1-醇和含有三级醇的2,3-二氢-1H-茚-1-醇。
• Tetrahydro-Naphthalene Derivatives as Glucocorticoid Receptor Modulators
  申请人：Edwards Christine

  公开号：US20070224130A1

  公开（公告）日：2007-09-27

  The present invention is directed to compounds of formula (I): wherein R represents a methyl or an ethyl group X represents N, C—H or C—CH 3 when X represents C—H or C—CH 3 , Y represents N when X represents N, Y represents C—H and physiologically functional derivatives thereof, pharmaceutical compositions comprising the compounds, the use of the compounds for the manufacture of medicaments particularly for the treatment of inflammatory and/or allergic conditions, processes for the preparation of the compounds, and chemical intermediates in the processes for the manufacture of the compounds.

  本发明涉及化合物公式(I)：其中R代表甲基或乙基基团，X代表N、C-H或C-CH3，当X代表C-H或C- 时，Y代表N，当X代表N时，Y代表C-H及其生理功能衍生物，包括该化合物的制药组合物，用于制造药物的化合物，特别是用于治疗炎症和/或过敏症状的药物，制备该化合物的过程以及制造该化合物的化学中间体。
• Tetrahydro-naphthalene derivatives as glucocorticoid receptor modulators
  申请人：Glaxo Group Limited

  公开号：US07902224B2

  公开（公告）日：2011-03-08

  The present invention is directed to compounds of formula (I): wherein R represents a methyl or an ethyl group X represents N, C—H or C—CH3 when X represents C—H or C—CH3, Y represents N when X represents N, Y represents C—H and physiologically functional derivatives thereof, pharmaceutical compositions comprising the compounds, the use of the compounds for the manufacture of medicaments particularly for the treatment of inflammatory and/or allergic conditions, processes for the preparation of the compounds, and chemical intermediates in the processes for the manufacture of the compounds.

  本发明涉及以下式子的化合物(I)：其中，R代表甲基或乙基基团，X代表N、C-H或C-CH3，当X代表C-H或C- 时，Y代表N；当X代表N时，Y代表C-H，以及其生理功能衍生物，包含该化合物的制药组合物，使用该化合物制造药物，特别是用于治疗炎症和/或过敏症的药物，制备该化合物的过程以及制造该化合物的化学中间体。
• Nonsteroidal Glucocorticoid Agonists: Tetrahydronaphthalenes with Alternative Steroidal A-Ring Mimetics Possessing Dissociated (Transrepression/Transactivation) Efficacy Selectivity
  作者：Keith Biggadike、Mohamed Boudjelal、Margaret Clackers、Diane M. Coe、Derek A. Demaine、George W. Hardy、Davina Humphreys、Graham G. A. Inglis、Michael J. Johnston、Haydn T. Jones、David House、Richard Loiseau、Deborah Needham、Philip A. Skone、Iain Uings、Gemma Veitch、Gordon G. Weingarten、Iain M. McLay、Simon J. F. Macdonald

  DOI：10.1021/jm070778w

  日期：2007.12.27

  The synthesis and biological activity of tetrahydronaphthalene derivatives coupled to various heterocycles are described. These compounds are potent glucocorticoid receptor agonists with efficacy selectivity in an NF kappa B glucocorticoid receptor (GR) agonist assay (representing transrepression effects) over an MMTV GR agonist assay (representing transactivation effects). Quinolones, indoles, and C- and N-linked quinolines are some of the heterocycles that provide efficacy selectivity. For example, the isoquinoline 49D1E2 has NF kappa B agonism with pIC(50) of 8.66 (89%) and reduced efficacy in MMTV agonism (6%), and the quinoline 55D1E1 has NF kappa B agonism with pIC(50) of 9.30 (101%) and reduced efficacy in MMTV agonism with pEC(50) of 8.02 (47%). A description of how a compound from each class is modeled in the active site of the receptor is given.