(2E,4E)-1,1-二乙氧基-2,4-己二烯 | 94088-28-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (2E,4E)-1,1-二乙氧基-2,4-己二烯
• 英文名称: 1,1-Diethoxyhexa-2,4-diene
• 英文别名: hexa-2t,4t-dienal-diethylacetal；Hexa-2t,4t-dienal-diaethylacetal；1,1-Diaethoxy-hexa-2t,4t-dien；Sorbinaldehyd-diaethylacetal；2,4-Hexadiene, 1,1-diethoxy-；(2E,4E)-1,1-diethoxyhexa-2,4-diene
• CAS: 94088-28-5
• 化学式: C₁₀H₁₈O₂
• 分子量: 170.252
• InChiKey: PDAPABBBKRHCMD-NUXDXBQRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2911000000

反应信息

• 作为反应物：
  描述：

  (2E,4E)-1,1-二乙氧基-2,4-己二烯 在 N-氯代丁二酰亚胺 、 正丁基锂 、 potassium tert-butylate 、 水 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.5h， 生成 (2E,4E)-6-Chlorohexa-2,4-dienal
  参考文献：
  名称：

  Tivola; Beccaria; Deagostino, Synthesis, 2000, # 11, p. 1615 - 1621

  摘要：

  DOI：
• 作为产物：
  描述：

  (E,E)-2,4-己二烯醛 、 原甲酸三乙酯 在 1-ethyl-3-methylimidazolium hydrogensulfate 作用下， 以 乙醇 为溶剂， 生成 (2E,4E)-1,1-二乙氧基-2,4-己二烯
  参考文献：
  名称：

  Acidic ionic liquid-catalyzed homologation of the polyene chain in α,β-enals (polyenals)

  摘要：

  An efficient green-chemistry synthesis of conjugated polyenals from alpha,beta-enals, orthoesters, and alkyl vinyl ethers promoted by acidic ionic liquid [emim][HSO4] is described. The ionic liquid can be reused at least three times without any decrease in product yields. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.11.005

文献信息

• Chemical Library and Structure–Activity Relationships of 11-Demethyl-12-oxo Calanolide A Analogues as Anti-HIV-1 Agents
  作者：Tao Ma、Li Liu、Hai Xue、Li Li、Chunyan Han、Lin Wang、Zhiwei Chen、Gang Liu

  DOI：10.1021/jm701405p

  日期：2008.3.13

  (+)-Calanolide A (1) as a natural product was previously found as an inhibitor of HIV-1 reverse tratiscriptase. In our further investigation of its template, racemic 11-demethyl-12-oxo calanolide A (15), which had two fewer chiral carbon centers at the C-11 and C-12 positions than (+)-calanolide A, had a comparably inhibitory activity and better therapeutic index (EC(50) = 0.11 mu M, TI = 818) against HIV-1 in vitro. A library based on its structural core was then designed and synthesized with introduction of nine diversity points in this article. The evaluations of anti-HIV-1 activity in vitro concluded their structure-activity relationships (SARs). A novel compound (10-bromomethyl-11-demethyl-12-oxo calanolide A, 123) was identified to have much higher inhibitory potency and therapeutic index (EC(50) = 2.85 nM, TI > 10,526) than those of the class compound against HIV-1. This finding provided a very important clue that modifications of the C ring at the C-10 position may be conducted to obtain drug candidates with better activity against HIV-1.

  (+)-Calanolide A (1) 作为一种天然产物，先前被发现是HIV-1逆转录酶的抑制剂。在我们对其模板的进一步研究中，外消旋的11-去甲基-12-酮基calanolide A (15) 被发现。与(+)-calanolide A相比，它在C-11和C-12位上少两个手性碳中心，但其对HIV-1的抑制活性相当，并且具有更好的治疗指数（EC(50) = 0.11 μM，TI = 818）。随后，基于其结构核心设计并合成了一个化合物库，并在本文中引入了九个多样性点。体外评估抗HIV-1活性得出了它们的结构-活性关系（SARs）。发现了一个新的化合物（10-溴甲基-11-去甲基-12-酮基calanolide A，123），其对HIV-1的抑制效力和治疗指数（EC(50) = 2.85 nM，TI > 10,526）显著高于该类化合物。这一发现提供了非常重要的线索，即对C环的C-10位进行修饰，可能会得到对HIV-1活性更好的药物候选物。
• A Short and Efficient New Synthesis of γ-Halo-Substituted α,β-Unsaturated Acetals and Carbonyl Compounds
  作者：Annamaria Deagostino、Paolo Balma Tivola、Cristina Prandi、Paolo Venturello

  DOI：10.1055/s-1999-2933

  日期：1999.11

  Treatment with N-bromosuccinimide (NBS) or N-chlorosuccinimide (NCS) of 1-subsituted 1-alkoxy-1,3-dienes, obtained by reaction of α,β-unsaturated acetals with LICKOR superbase, affords γ-brominated (chlorinated) α,β-unsaturated acetals or carbonyl compounds, according to the selected experimental conditions.

  用N-溴代琥珀酰亚胺（NBS）或N-氯代琥珀酰亚胺（NCS）处理由α,β-不饱和醛与LICKOR超级碱反应得到的1-取代1-烷氧基-1,3-二烯，能够根据选定的实验条件获得γ-溴化（氯化）α,β-不饱和醛或羰基化合物。
• METHOD FOR PRODUCING 2,4-DIENAL ACETAL COMPOUND AND 2,4-DIENAL COMPOUND
  申请人：SHIN-ETSU CHEMICAL CO., LTD.

  公开号：US20180305276A1

  公开（公告）日：2018-10-25

  Methods of producing a 2,4-dienal acetal compound and a 2,4-dienal compound useful as synthesis intermediates of a sex pheromone compound having a conjugated diene structure or a conjugated triene structure. More specifically, a method produces a 2,4-dienal acetal compound of Formula (2): R 1 CH═CH—CH═CH—CH(OR 2 )(OR 3 ), including a step of subjecting a 2-enal acetal compound having a leaving group X at position C5 and being expressed by Formula (1): R 1 CHX—CH 2 —CH═CH—CH(OR 2 )(OR 3 ) to an elimination reaction in the presence of a base to obtain the 2,4-dienal acetal compound (2); and a method for producing a 2,4-dienal compound of Formula (3): R 1 CH═CH—CH═CH—CHO, further including a step of deprotecting the 2,4-dienal acetal compound (2) to obtain the 2,4-dienal compound (3).

  生产2,4-二烯醛缩醛化合物和用作合成昆虫信息素化合物的中间体的2,4-二烯醛化合物的方法。更具体地，一种方法生产公式（2）的2,4-二烯醛缩醛化合物：R1CH═CH—CH═CH—CH(OR2)(OR3)，包括在碱存在下使具有在C5位置上具有离去基团X并由公式（1）表示的2-烯醛缩醛化合物经消除反应制得2,4-二烯醛缩醛化合物（2）的步骤；以及生产公式（3）的2,4-二烯醛化合物的方法：R1CH═CH—CH═CH—CHO，进一步包括去保护2,4-二烯醛缩醛化合物（2）以获得2,4-二烯醛化合物（3）的步骤。
• TETRACYCLIC DIPYRANO-COUMARIN COMPOUNDS WITH ANTI-HIV AND ANTI-MYCOBACTERIUM TUBERCULOSIS ACTIVITIES
  申请人：Liu Gang

  公开号：US20100324067A1

  公开（公告）日：2010-12-23

  The present invention relates to tetracyclodipyrano-coumarin compounds of general formula (I), wherein the substituents are defined herein. These compounds exihibit dual biological activities of anti human immunodeficiency virus type 1 (HIV-1) infection and anti- Mycobacterium Tuberculosis (TB) infection.

  本发明涉及通式（I）的四环二吡喃香豆素类化合物，其中取代基在此定义。这些化合物表现出抗人类免疫缺陷病毒类型1（HIV-1）感染和抗结核分枝杆菌（TB）感染的双重生物活性。
• TETRIACYCLODIPYRANYL COUMARINS AND THE ANTI-HIV AND ANTI-TUBERCULOSIS USES THEREOF
  申请人：Institute of Mataria Medica, Chinese Academy of Medical Sciences

  公开号：EP2216335A1

  公开（公告）日：2010-08-11

  The present invention relates to tctracyclodipyrano-coumarin compounds of general formula (I), wherein the substituents are defined herein. These compounds exihibit dual biological activities of anti human immunodeficiency virus type 1 (HIV-1) infection and anti-Mycobacterium Tuberculosis (TB) infection.

  本发明涉及通式(I)的三环二吡喃香豆素化合物，其中取代基在本文中定义。这些化合物具有抗人类免疫缺陷病毒 1 型（HIV-1）感染和抗结核分枝杆菌（TB）感染的双重生物活性。