2-ethyl-5-methoxyindanone | 138090-26-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 2-ethyl-5-methoxyindanone
• 英文别名: 2-Ethyl-5-methoxy-2,3-dihydroinden-1-one
• CAS: 138090-26-3
• 化学式: C₁₂H₁₄O₂
• 分子量: 190.242
• InChiKey: IBRZNRUQGXAFGW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 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：

  2-ethyl-5-methoxyindanone 在 四氢吡咯 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成 9a-Ethyl-7-methoxy-1,2,9,9a-tetrahydro-fluoren-3-one
  参考文献：
  名称：

  The discovery of tetrahydrofluorenones as a new class of estrogen receptor β-subtype selective ligands

  摘要：

  Synthesis and derivatization of a series of substituted tetrahydrofluorenone analogs giving potent, ERbeta subtype selective ligands are described. Several analogs possessing ERbeta binding affinities comparable to 17beta-estradiol but with greater than 75-fold selectivity over ERalpha are reported.

  DOI：

  10.1016/j.bmcl.2006.03.098
• 作为产物：
  描述：

  5-甲氧基-1-茚酮 、 碘乙烷 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-ethyl-5-methoxyindanone
  参考文献：
  名称：

  The discovery of tetrahydrofluorenones as a new class of estrogen receptor β-subtype selective ligands

  摘要：

  Synthesis and derivatization of a series of substituted tetrahydrofluorenone analogs giving potent, ERbeta subtype selective ligands are described. Several analogs possessing ERbeta binding affinities comparable to 17beta-estradiol but with greater than 75-fold selectivity over ERalpha are reported.

  DOI：

  10.1016/j.bmcl.2006.03.098

文献信息

• 5,6,11,12-Tetrahydrochrysenes: synthesis of rigid stilbene systems designed to be fluorescent ligands for the estrogen receptor
  作者：Kwang Jin Hwang、James P. O'Neil、John A. Katzenellenbogen

  DOI：10.1021/jo00030a039

  日期：1992.2

  We have prepared a series of tetrahydrochrysenes as fluorescent ligands for the estrogen receptor. The stilbene chromophore in this tetracyclic system is held rigid and is adorned with an electron-donating hydroxyl group at C-8 that corresponds to the phenolic hydroxyl of estrogens and an electron acceptor at C-2 to give a donor-acceptor fluorophore. Additional substituents at C-5 and C-11 provide additional bulk that improves receptor binding affinity without distorting the planar conjugated system. The tetrahydrochrysene core was prepared by an acyloin condensation of alpha-alkyl m-methoxyhydrocinnamate esters, followed by a double dehydrative cyclization. The cis and trans isomers of the alkyl substituted systems could be separated and their stereochemistry ascertained by X-ray crystallographic analysis; the trans isomer has the higher receptor binding affinity, and the derivative with ethyl substituents at C-5 and C-11 has the best affinity. The donor-acceptor systems were prepared by functional group manipulations on one of the aromatic methoxy groups: conversion to the trifluoromethanesulfonate was followed by a palladium-mediated carbonylation to give the acetyl derivative and methoxycarbonylation to give the ester. The ester was further elaborated to the amide and nitrile. The nitro compound was prepared by nitration of protio system, itself prepared by hydrogenolysis of the trifluoromethanesulfonate. As will be described later, these tetrahydrochrysenes provide a favorable combination of estrogen receptor binding affinity and long wavelength, high quantum yield fluorescence to make them useful as fluorescent ligands for the estrogen receptor.
• [DE] MITTEL ZUM BEEINFLUSSEN DER WIRKUNGEN VON ORGANOPHOSPHORVERBINDUNGEN UND VERWENDUNG VON GALANTHAMIN, DESSEN DERIVATEN UND ANALOGA ZUM HERSTELLEN SOLCHER MITTEL<br/>[EN] COMPOSITIONS FOR INFLUENCING THE EFFECTS OF ORGANOPHOSPHORUS COMPOUNDS AND USE OF GALANTHAMINE, ITS DERIVATIVES AND ANALOGUES FOR PRODUCING SUCH COMPOSITIONS<br/>[FR] AGENT SERVANT À INFLUENCER LES EFFETS DE COMPOSÉS ORGANOPHOSPHORÉS ET UTILISATION DE GALANTHAMINE, DE SES DÉRIVÉS ET ANALOGUES POUR LA FABRICATION D'UN TEL AGENT
  申请人：SANOCHEMIA LTD

  公开号：WO2008022365A2

  公开（公告）日：2008-02-28

  [EN] The use of galanthamine of the formula and derivatives or analogues of galanthamine for controlling the effect of toxic organic phosphorus compounds such as parathion, paraxon, sarin, soman or tabun is described, wherein a composition comprising the said compound or a combination of at least two of the said compounds is administered before and/or after contact of a human with the toxic organic phosphorus compound.
  [FR] L'invention concerne l'utilisation de galanthamine de formule (I) et de dérivés ou d'analogues de galanthamine pour lutter contre les effets de composés de phosphore organiques toxiques, tels que la parathione, la paraxone, le sarin, le soman ou le tabun. Selon l'invention, un agent contenant ledit composé ou une combinaison d'au moins deux desdits composés est administré avant et/ou après le contact d'un humain avec le composé de phosphore organique toxique.
  [DE] Beschrieben wird die Verwendung von Galanthamin der Formel (I) und Derivaten oder Analoga des Galanthamins zum Bekämpfen der Wirkung von giftigen organischen Phosphorverbindungen, wie Parathion, Paraxon, Sarin, Soman oder Tabun, indem ein die genannte Verbindung oder eine Kombination aus wenigstens zwei der genannten Verbindungen enthaltendes Mittel vor und/oder nach dem Kontakt eines Menschen mit der giftigen organischen Phosphorverbindung verabreicht wird.
• The discovery of tetrahydrofluorenones as a new class of estrogen receptor β-subtype selective ligands
  作者：R.R. Wilkening、R.W. Ratcliffe、E.C. Tynebor、K.J. Wildonger、A.K. Fried、M.L. Hammond、R.T. Mosley、P.M.D. Fitzgerald、N. Sharma、B.M. McKeever、S. Nilsson、M. Carlquist、A. Thorsell、L. Locco、R. Katz、K. Frisch、E.T. Birzin、H.A. Wilkinson、S. Mitra、S. Cai、E.C. Hayes、J.M. Schaeffer、S.P. Rohrer

  DOI：10.1016/j.bmcl.2006.03.098

  日期：2006.7

  Synthesis and derivatization of a series of substituted tetrahydrofluorenone analogs giving potent, ERbeta subtype selective ligands are described. Several analogs possessing ERbeta binding affinities comparable to 17beta-estradiol but with greater than 75-fold selectivity over ERalpha are reported.