1-(4-methoxy-phenyl)-5-methyl-hexan-3-one | 15540-09-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-(4-methoxy-phenyl)-5-methyl-hexan-3-one
• 英文别名: 1-(4-Methoxy-phenyl)-5-methyl-hexan-3-on；1-(4-methoxyphenyl)-5-methylhexan-3-one
• CAS: 15540-09-7
• 化学式: C₁₄H₂₀O₂
• 分子量: 220.312
• InChiKey: QGARRKMFDNQJSE-UHFFFAOYSA-N

物化性质

• 沸点：
  165-167 °C(Press: 11 Torr)
• 密度：
  0.9999 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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-(4-methoxy-phenyl)-5-methyl-hexan-3-one 在 锌 吡啶 、 sodium tetrahydroborate 、 四溴化碳 、 三氯化铁 、 铜 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三苯基膦 、 sodium iodide 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 41.67h， 生成 2-Diazo-4-[2-(4-methoxy-phenyl)-ethyl]-6-methyl-heptanoic acid ethyl ester
  参考文献：
  名称：

  Cyclopentane Construction by Rh-Catalyzed Intramolecular C−H Insertion:  Relative Reactivity of a Range of Catalysts

  摘要：

  The preparation and Rh-mediated cyclization of the alpha-diazoester 1 are outlined, and its utility in determining the elements that contribute to the reactivity of the intermediate Rh-carbenoid is presented. The rate of disappearance of diazo ester 1 catalyzed by several representative Rh(II) complexes was determined. The observed relative rate constants for the reaction of the Rh(II) complexes with 1 varied over a range of >10(7). The reactivity of the Rh-carbenoid intermediate was explored using the ratio of the sum of (3 + 4 + 5) to 2 (cyclization vs elimination), the ratio of 3 to the sum of (4 + 5) (chemo selectivity), and the ratio of 4 to 5 (diastereoselectivity). It is striking that these four measures of reactivity were found to be independent of each other.

  DOI：

  10.1021/jo0303766
• 作为产物：
  描述：

  4-甲基-2-戊酮 在 palladium on activated charcoal 氢气 、 对甲苯磺酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 5.33h， 生成 1-(4-methoxy-phenyl)-5-methyl-hexan-3-one
  参考文献：
  名称：

  Cyclopentane Construction by Rh-Catalyzed Intramolecular C−H Insertion:  Relative Reactivity of a Range of Catalysts

  摘要：

  The preparation and Rh-mediated cyclization of the alpha-diazoester 1 are outlined, and its utility in determining the elements that contribute to the reactivity of the intermediate Rh-carbenoid is presented. The rate of disappearance of diazo ester 1 catalyzed by several representative Rh(II) complexes was determined. The observed relative rate constants for the reaction of the Rh(II) complexes with 1 varied over a range of >10(7). The reactivity of the Rh-carbenoid intermediate was explored using the ratio of the sum of (3 + 4 + 5) to 2 (cyclization vs elimination), the ratio of 3 to the sum of (4 + 5) (chemo selectivity), and the ratio of 4 to 5 (diastereoselectivity). It is striking that these four measures of reactivity were found to be independent of each other.

  DOI：

  10.1021/jo0303766

文献信息

• Inhibitors of hepatitis C virus RNA-dependent RNA polymerase, and compositions and treatments using the same
  申请人：Borchardt Allen

  公开号：US20050176701A1

  公开（公告）日：2005-08-11

  The invention relates to compounds of the formula 1 and to pharmaceutically acceptable salts, solvates, prodrugs and metabolites thereof, wherein W, Z, R 1 and R 2 , are as defined herein. The invention also relates to methods of treating Hepatitis C virus in mammals by administering the compounds of formula 1, and to pharmaceutical compositions for treating such disorders, which contain the compounds of formula 1. The invention also relates to methods of preparing the compounds of formula 1.

  这项发明涉及公式1的化合物，以及其药学上可接受的盐、溶剂化合物、前药和代谢物，其中W、Z、R1和R2如本文所定义。该发明还涉及通过给哺乳动物施用公式1的化合物来治疗丙型肝炎病毒的方法，以及用于治疗这类疾病的含有公式1化合物的药物组合物。该发明还涉及制备公式1化合物的方法。
• A novel ketone synthesis by a palladium-catalyzed reaction of thiol esters and organozinc reagents
  作者：Hidetoshi Tokuyama、Satoshi Yokoshima、Tohru Yamashita、Tohru Fukuyama

  DOI：10.1016/s0040-4039(98)00456-0

  日期：1998.5

  A variety of ketones have been prepared by a palladium-catalyzed reaction of ethanethiol esters with organozinc reagents. Various functional groups, including esters, ketones, aromatic halides and aldehydes, tolerate the reaction conditions. The reaction can also be applied to the synthesis of α-amino ketones using the corresponding L-α-amino thiol esters without racemization.

  通过乙硫醇酯与有机锌试剂的钯催化反应已制备了多种酮。包括酯，酮，芳族卤化物和醛在内的各种官能团可耐受反应条件。该反应也可用于使用相应的L-α-氨基硫醇酯而无需外消旋作用的合成α-氨基酮。
• INHIBITORS OF HEPATITIS C VIRUS RNA-DEPENDENT RNA POLYMERASE, AND COMPOSITIONS AND TREATMENTS USING THE SAME
  申请人：Borchardt Allen

  公开号：US20060189681A1

  公开（公告）日：2006-08-24

  The invention relates to compounds of the formula 1 and to pharmaceutically acceptable salts, solvates, prodrugs and metabolites thereof, wherein W, Z, R 1 and R 2 , are as defined herein. The invention also relates to methods of treating Hepatitis C virus in mammals by administering the compounds of formula 1, and to pharmaceutical compositions for treating such disorders, which contain the compounds of formula 1. The invention also relates to methods of preparing the compounds of formula 1.

  本发明涉及式1的化合物以及其药学上可接受的盐、溶剂合物、前药和代谢物，其中W、Z、R1和R2如本文所定义。本发明还涉及通过给哺乳动物投予式1的化合物来治疗丙型肝炎病毒的方法，以及包含式1的化合物的用于治疗此类疾病的制药组合物。本发明还涉及制备式1的化合物的方法。
• Studies in sesquiterpenes—XXIV
  作者：M.V.R. Koteswara Rao、G.S. Krishna Rao、Sukh Dev

  DOI：10.1016/s0040-4020(01)82270-5

  日期：1966.1

  A total synthesis of (±)-4-isopropyl-trans-decalin-1,6-dione, a key intermediate in the cadinane series, and its conversion into (±)-cadinene dihydrochloride, is reported.

  据报道，全合成的（±）-4-异丙基-反式-癸烷-1,6-二酮是卡丁烷系列中的关键中间体，并已转化为（±）-卡丹烯二盐酸盐。
• [EN] INHIBITORS OF HEPATITIS C VIRUS RNA-DEPENDENT RNA POLYMERASE, AND COMPOSITIONS AND TREATMENTS USING THE SAME<br/>[FR] INHIBITEURS DE L'ARN POLYMERASE ARN-DEPENDANTE DU VIRUS DE L'HEPATITE C, ET COMPOSITIONS ET TRAITEMENTS FAISANT APPEL A CET INHIBITEUR
  申请人：PFIZER

  公开号：WO2004074270A3

  公开（公告）日：2004-12-23