1-溴-2-异丙基-3,4-二甲氧基苯 | 77256-01-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-溴-2-异丙基-3,4-二甲氧基苯
• 英文名称: 1-bromo-2-isopropyl-3,4-dimethoxybenzene
• 英文别名: 1-bromo-2-isopropyl-3,4-dimethoxy-benzene；1-Brom-2-isopropyl-3,4-dimethoxy-benzol；4-Brom-3-isopropyl-veratrol；6-Brom-2.3-dimethoxy-cumol；1-bromo-3,4-dimethoxy-2-propan-2-ylbenzene
• CAS: 77256-01-0
• 化学式: C₁₁H₁₅BrO₂
• 分子量: 259.143
• InChiKey: YZOHSCYWLIGWAR-UHFFFAOYSA-N

物化性质

• 沸点：
  122-125 °C(Press: 3 Torr)
• 密度：
  1.326 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2909309090

反应信息

• 作为反应物：
  描述：

  1-溴-2-异丙基-3,4-二甲氧基苯 在 10% palladium on active carbon 氢氧化钾 、 sodium tetrahydroborate 、 邻四氯苯醌 、 硫酸 、 乙基溴化镁 、 氢气 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 高氯酸 、 二氯甲烷 、 溶剂黄146 、 丙酮 为溶剂， 25.0~215.0 ℃ 、344.73 kPa 条件下， 反应 10.5h， 生成 5,5'-diisopropyl-1,1',6,6',7,7'-hexamethoxy-3,3'-dimethyl-2,2'-binaphthalene
  参考文献：
  名称：

  Efficient synthesis of the gossypol binaphthyl backbone

  摘要：

  DOI：

  10.1021/jo00328a029
• 作为产物：
  描述：

  3-甲氧基水杨酸 生成 1-溴-2-异丙基-3,4-二甲氧基苯
  参考文献：
  名称：

  Efficient synthesis of the gossypol binaphthyl backbone

  摘要：

  DOI：

  10.1021/jo00328a029

文献信息

• Synthesis of Gossypol Analogues
  作者：Vassil I. Ognyanov、Orlin S. Petrov、Emil P. Tiholov、Nikola M. Mollov

  DOI：10.1002/hlca.19890720221

  日期：1989.3.15

  Two gossypol analogues 2a and 2b were synthesized for biological evaluation as male contraceptive agents. The naphthol 8c was prepared by analogy with a known procedure starling from 3-isopropylcatechol (3). (t-Bu)2O2-Mediated phenolic coupling of 8c furnished the binaphthol 9c which, after pyrane ring closure, deprotection. and selective bisformylation with SnCl4/Cl2CHOCH3, gave the target compound

  合成了两种棉酚类似物2a和2b作为男性避孕药进行了生物学评估。萘酚8c通过类似的方法由3-异丙基邻苯二酚（3）开始制备。（t -Bu ）2 O 2-介导的8c酚偶联提供了联萘酚9c，在吡喃环闭合后，联萘酚9c脱保护。并用SnCl 4 / Cl 2 CHOCH 3选择性双甲酰化，得到目标化合物2a。以类似的方式制备相应的四羟基类似物2b。
• Ir-Catalyzed Enantioselective, Intramolecular Silylation of Methyl C–H Bonds
  作者：Bo Su、John F. Hartwig

  DOI：10.1021/jacs.7b06679

  日期：2017.9.6

  We report highly enantioselective intramolecular, silylations of unactivated, primary C(sp3)–H bonds. The reactions form dihydrobenzosiloles in high yields with excellent enantioselectivities by functionalization of enantiotopic methyl groups under mild conditions. The reaction is catalyzed by an iridium complex generated from [Ir(COD)OMe]2 and chiral dinitrogen ligands that we recently disclosed.

  我们报告高度对映选择性分子内，未激活的，主要的C（sp 3）–H键的甲硅烷基化。通过在温和条件下对映体甲基官能化，该反应以高收率形成具有优异对映选择性的二氢苯并甲硅烷。反应是由[Ir（COD）OMe] 2和我们最近公开的手性二氮配体生成的铱配合物催化的。对映体富集的二氢苯并甲硅烷中的C-Si键进一步转化为最终产品中的C-Cl，C-Br，C-I和C-O键。通过顺序C（sp 3）–H和C（sp 2）–H甲硅烷基化和官能化，以及包含多种类型的C–H键的手性天然产物衍生物的非对映选择性C–H甲硅烷基化。初步的机理研究表明，C–H裂解是决定速率的步骤。
• Deoxygossylic compounds
  申请人：University of New Mexico

  公开号：US05936120A1

  公开（公告）日：1999-08-10

  The invention provides deoxygossylic compounds having useful biological activities, and methods for the synthesis of these and related compounds. The invention further provides valuable intermediates for the synthesis of the compounds, and pharmaceutical compositions containing biologically active compounds according to the invention.

  本发明提供了具有有用生物活性的脱氧高酸化合物，以及这些和相关化合物的合成方法。本发明还提供了用于合成化合物的有价值的中间体，以及包含根据本发明的生物活性化合物的药物组合物。
• Synthesis of hemigossypol and its derivatives
  作者：Jun Wei、David L. Vander Jagt、Robert E. Royer、Lorraine M. Deck

  DOI：10.1016/j.tetlet.2010.08.089

  日期：2010.11

  Hemigossypol (3), a sesquiterpene natural product, was previously isolated from Gossypium barbadense and was shown to display improved anti-furgal activity compared to gossypol (1), the disesquiterpene chiller of hemigossypol (3). Gossypol exhibits multiple biological activities. In order to study whether hemigossypol and its derivatives retain the various bioactivities of gossypol, we developed a short and convenient synthetic scheme to synthesize hemigossypol. This is the first de novo synthesis of this natural product. In addition derivatives of hemigossypol with various 2,5-alkyl substituents were synthesized. Modification of the synthetic scheme also afforded the natural product hemigossylic lactone (4) and its 2,5-substituted derivatives. (C) 2010 Elsevier Ltd. All rights reserved.
• Synthesis and Anti-HIV Activity of 1,1'-Dideoxygossypol and Related Compounds
  作者：Robert E. Royer、Lorraine M. Deck、Timothy J. Vander Jagt、Francella J. Martinez、Ray G. Mills、Stephen A. Young、David L. Vander Jagt

  DOI：10.1021/jm00013a018

  日期：1995.6

  1,1'-Dideoxygossypol (DDG), 1,1'-dideoxygossylic acid (DDGA), 8-deoxyhemigossypol (DHG), and 8-deoxyhemigossylic acid (DHGA) were synthesized and tested for their ability to inhibit the replication of HIV in vitro. The EC(50) for DDGA was <1 mu M, and its threshold cytotoxicity was approximately 20 mu M. DDG was less effective than DDGA against HIV and showed considerable toxicity at 5 mu M. DHGA was ineffective against HN and had very low cytotoxicity. DHG showed some anti-HIV activity, but the threshold cytotoxicity was 5 mu M. The dissociation constants for the binding of the four compounds to human serum albumin were determined by fluorescence quenching titrations, and all four were found to have much lower affinities for albumin than the parent compound gossypol.