5,11-二乙基-5,6,11,12-四氢-2,8-屈二醇 | 138090-06-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 中文名称: 5,11-二乙基-5,6,11,12-四氢-2,8-屈二醇
• 中文别名: 8-[[4-(1,1-二甲基乙基)-2-磺酸根苯基]氨基]-9,10-二氢-1-羟基-5-[(1-甲基乙基)氨基]-9,10-二羰基蒽-2-磺化二钠；(5R,11R)-rel-5,11-二乙基-5,6,11,12-四氢-2,8-屈二醇
• 英文名称: (R,R)-cis-diethyl tetrahydro-2,8-chrysenediol
• 英文别名: (5R,11R)-5,11-diethyl-5,6,11,12-tetrahydrochrysene-2,8-diol
• CAS: 138090-06-9；221368-54-3
• 化学式: C₂₂H₂₄O₂
• 分子量: 320.431
• InChiKey: MASYAWHPJCQLSW-ZIAGYGMSSA-N

物化性质

• 熔点：
  >189°C (dec)
• 沸点：
  519.0±50.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)
• 溶解度：
  二甲基亚砜：20 毫克/毫升

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• WGK Germany：
  3
• 安全说明：
  S22

制备方法与用途

cis-5,11-二乙基-5,6,11,12-二氢-2,8-蔥二醇是一种用于雌激素受体的荧光配体。一系列四氢蔥衍生物也被制备出来，用作雌激素受体的荧光配体。

反应信息

• 作为产物：
  描述：

  rac-2,8-dimethoxy-5,11-diethyl-5,6,11,12-tetrahydrochrysene 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 生成 5,11-二乙基-5,6,11,12-四氢-2,8-屈二醇
  参考文献：
  名称：

  雌激素受体亚型选择性配体：顺式和反式-5,11-二烷基-5,6,11，12-四氢瓜氨酸的不对称合成和生物学评估。

  摘要：

  我们最近报道，外消旋5,11-顺二乙基-5,6,11，12-四氢丙烯-2,8-二醇（THC，rac-2b）充当雌激素受体α（ERalpha）的激动剂和雌激素受体β（ERbeta）的完全拮抗剂（Sun et al。Endocrinology 1999，140，800-804）。为了进一步研究这种新颖的ER亚型选择性雌激素活性，我们合成了一系列顺式和反式二烷基四氢大麻酚。通过对映体纯的α-烷基-β-芳基丙酸酯的酰基糊精缩合，然后在温度下，在路易斯酸介导的双环化下，以高度对映和非对映选择性的方式制备顺式-二甲基，-二乙基和-二丙基THC 2a-c。最小差向异构的条件。ERalpha和ERbeta的顺式和反式异构体的二甲基，二乙基，在竞争性结合试验中测定了二丙基四氢大麻酚的含量，在哺乳动物细胞中通过报道基因测定了它们的转录活性。发现几乎所有检查的THC对ERbeta都具有亲和力。所有这些THC都是

  DOI：

  10.1021/jm990101b

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.
• SCREEN FOR INHIBITORS OF FILOVIRUS AND USES THEREFOR
  申请人：Wisconsin Alumni Research Foundation (WARF)

  公开号：US20160115518A1

  公开（公告）日：2016-04-28

  The invention provides methods to identify agents useful to prevent, inhibit or treat viral infections, e.g., filovirus infections, as well as compositions having one or more agents to prevent, inhibit or treat viral infection.
• US9222118B2
  申请人：——

  公开号：US9222118B2

  公开（公告）日：2015-12-29
• [EN] SCREEN FOR INHIBITORS OF FILOVIRUS AND USES THEREFOR<br/>[FR] CRIBLAGE D'INHIBITEURS DE FILOVIRUS ET LEURS UTILISATIONS
  申请人：KAWAOKA YOSHIHIRO

  公开号：WO2010053573A2

  公开（公告）日：2010-05-14

  The invention provides methods to identify agents useful to prevent, inhibit or treat viral infections, e.g., filovirus infections, as well as compositions having one or more agents to prevent, inhibit or treat viral infection.
• Estrogen Receptor Subtype-Selective Ligands:  Asymmetric Synthesis and Biological Evaluation of <i>cis</i>- and <i>trans</i>-5,11-Dialkyl- 5,6,11,12-tetrahydrochrysenes
  作者：Marvin J. Meyers、Jun Sun、Kathryn E. Carlson、Benita S. Katzenellenbogen、John A. Katzenellenbogen

  DOI：10.1021/jm990101b

  日期：1999.7.1

  activity, we have synthesized a series of cis- and trans-dialkyl THCs. cis-Dimethyl, -diethyl, and -dipropyl THCs 2a-c were prepared in a highly enantio- and diastereoselective manner by the acyloin condensation of enantiomerically pure alpha-alkyl-beta-arylpropionic esters, followed by a Lewis acid-mediated double cyclization under conditions of minimal epimerization. ERalpha and ERbeta binding affinity

  我们最近报道，外消旋5,11-顺二乙基-5,6,11，12-四氢丙烯-2,8-二醇（THC，rac-2b）充当雌激素受体α（ERalpha）的激动剂和雌激素受体β（ERbeta）的完全拮抗剂（Sun et al。Endocrinology 1999，140，800-804）。为了进一步研究这种新颖的ER亚型选择性雌激素活性，我们合成了一系列顺式和反式二烷基四氢大麻酚。通过对映体纯的α-烷基-β-芳基丙酸酯的酰基糊精缩合，然后在温度下，在路易斯酸介导的双环化下，以高度对映和非对映选择性的方式制备顺式-二甲基，-二乙基和-二丙基THC 2a-c。最小差向异构的条件。ERalpha和ERbeta的顺式和反式异构体的二甲基，二乙基，在竞争性结合试验中测定了二丙基四氢大麻酚的含量，在哺乳动物细胞中通过报道基因测定了它们的转录活性。发现几乎所有检查的THC对ERbeta都具有亲和力。所有这些THC都是