1-[2-[2-[2-(2-甲氧基乙氧基)乙氧基]乙氧基]乙氧基]蒽-9,10-二酮 | 104549-31-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 中文名称: 1-[2-[2-[2-(2-甲氧基乙氧基)乙氧基]乙氧基]乙氧基]蒽-9,10-二酮
• 英文名称: 1-(2-(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)ethoxy)anthracene-9,10-dione
• 英文别名: 1-[2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethoxy]-9,10-anthraquinone；1-(2,5,8,11-Tetraoxatridecan-13-yloxy)anthracene-9,10-dione；1-[2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethoxy]anthracene-9,10-dione
• CAS: 104549-31-7
• 化学式: C₂₃H₂₆O₇
• 分子量: 414.455
• InChiKey: ZKLLKVHVASAOCF-UHFFFAOYSA-N

物化性质

• 熔点：
  70-72 °C
• 沸点：
  552.2±50.0 °C(Predicted)
• 密度：
  1.216±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  30
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-[2-[2-[2-(2-甲氧基乙氧基)乙氧基]乙氧基]乙氧基]蒽-9,10-二酮 、 烯丙醇 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以18%的产率得到1-(prop-2'-enyloxy)anthraquinone
  参考文献：
  名称：

  Alkynes and poly(ethylene glycol) derivatives as nucleophiles and catalysts in substitution reactions of 1-chloroanthraquinones

  摘要：

  Two synthetically useful approaches to 1-substituted anthraquinone derivatives are reported. Application of these methods afforded the following 1-anthraquinyl ethers: n-propyl, n-butyl, n-octyl, n-nonyl, n-hexadecyl, isoamyl, allyl, 2-butenyl, (E)-2-hexenyl, (E)-2-tridecyl, benzyl, phenyl, 4-methylphenyl, 2-butynyl, 2-pentynyl, 2-hexynyl, 3-pentynyl, 3-hexynyl, 3-heptynyl, 3-nonynyl, 4-hexynyl, 4-heptynyl, 5-heptynyl, 5-octynyl, 5-nonynyl, 2-methoxyethyl, 2-(2-methoxyethoxy)ethyl, 2-[2-[2-(octadecyloxy)ethoxy]ethoxy]ethyl, 2-(methylthio)ethyl, 2-(1-piperidino)ethyl, and 2-(1-morpholino)ethyl. The results of about 100 nucleophilic substitution reactions (a number were duplicates) are presented. Most of these reactions involve either a new approach, new products, or both. Included are displacements of chloride by alkanols, alkenols, and alkynols. Of the three, only the latter afford acceptable yields of product, although lower yields are observed as the distance between hydroxyl and triple bond increases. Nucleophiles of the type RO(CH2CH2O)nOH proved remarkably effective. Alkynyl ethers and poly(oxyethylene) ethers also proved to be excellent leaving groups. Both alkynols and oligoethylene glycol monoethers were found to be catalysts for the conversion of 1-chloroanthraquinone into 1-anthraquinyl ethers. In an attempt to understand the mechanism of this reaction, solid-state structures of four anthraquinone derivatives have been obtained. These have poly(ethyleneoxy), morpholino, or alkynyl side arms.

  DOI：

  10.1021/jo00025a021
• 作为产物：
  描述：

  四乙基乙二醇单甲酯 、 1-氯蒽醌 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以65.69%的产率得到1-[2-[2-[2-(2-甲氧基乙氧基)乙氧基]乙氧基]乙氧基]蒽-9,10-二酮
  参考文献：
  名称：

  使用Podands作为亲核试剂和离去基团对蒽醌进行非凡的亲核取代

  摘要：

  饱和醇和1-氯蒽醌之间的亲核芳族取代反应通常较差，但当使用聚乙二醇单甲醚作为亲核试剂或以醇为亲核试剂且podand为离去基团时，收率较高。

  DOI：

  10.1016/s0040-4039(00)94332-6

文献信息

• Novel selective algaecides for control of cyanochloronta
  申请人：——

  公开号：US20040116536A1

  公开（公告）日：2004-06-17

  We have now discovered that certain 9,10-anthraquinone derivatives we developed possess potent activity against O. perornata while possessing a sufficiently high level of solubility in water to make their activity against O. perornata viable. These compounds possess a high level of activity against O. perornata yet are relatively non-toxic to green algae and fishes. The compounds also possess a relatively short half-life. The compounds represent a new means to providing compounds possessing a high degree of selective activity against blue-green algae while being physiologically tolerated by catfish and green algae. The compounds provide a means for controlling blue-green algae in managed bodies of water that are destined for public use or consumption.

  我们现在发现，我们开发的某些9,10-蒽醌衍生物具有对O. perornata的强效活性，同时具有足够高的水溶性，使它们对O. perornata的活性变得可行。这些化合物具有对O. perornata的高活性，但相对于绿藻和鱼类来说毒性较小。这些化合物也具有相对较短的半衰期。这些化合物代表了一种新的手段，提供了一种高度选择性对抗蓝藻的化合物，同时被鲶鱼和绿藻生理耐受。这些化合物提供了一种控制管理水体中蓝藻的手段，这些水体将用于公共使用或消费。
• Electrochemical switching in anthraquinone-substituted carbon-pivot lariat ethers and podands: chain length effects in geometric and electronic cooperativity
  作者：Deborah A. Gustowski、Milagros. Delgado、Vincent J. Gatto、Luis. Echegoyen、George W. Gokel

  DOI：10.1021/ja00284a019

  日期：1986.11

  Synthese d'une serie d'anthraquinones substituees en −1 (ou Ar) par le substituant E=−CH 2 CH 2 - avec formation d'Ar-OCH 3 , Ar-OEOEOCH 3 , Ar-OEOEOEOCH 3 , Ar-OEOEOEOEOCH 3 , Ar-OEOEOEOEOEOCH 3 , Ar-OEOEOEO-Ar et d'Ar-O-CH 2 -15-crown-5. Mise en evidence de l'existence de couples redox a un ou 2 electrons (voltammetrie cyclique) dans le cas des differents systemes lors de l'addition d'ions Li +

  Synthese d'une serie d'anthraquinones substituees en -1 (ou Ar) par le substituant E=−CH 2 CH 2 - avec 形成 d'Ar-OCH 3 , Ar-OEOEOCH 3 , Ar-OEOEOEOCH 3 , Ar-OEOEOEOCH 3 ，Ar-OEOEOEOEOEOCH 3 ，Ar-OEOEOEO-Ar 和 d'Ar-O-CH 2 -15-crown-5。Mise en evidence de l'existence de Couples redox a un ou 2 electrons (voltammetrie cyclique) dans le cas des differents systemes lors de l'addition d'ions Li + , Na + et K +
• HYUNSOOK, KIM YOO;DAVIS, DAWN M.;CHEN, ZHIHONG;ECHEGOYEN, LUIS;GOKEL, GEO+, TETRAHEDRON LETT., 31,(1990) N, C. 55-58
  作者：HYUNSOOK, KIM YOO、DAVIS, DAWN M.、CHEN, ZHIHONG、ECHEGOYEN, LUIS、GOKEL, GEO+

  DOI：——

  日期：——
• US6949250B2
  申请人：——

  公开号：US6949250B2

  公开（公告）日：2005-09-27
• [EN] NOVEL SELECTIVE ALGAECIDES FOR CONTROL OF CYANOCHLORONTA<br/>[FR] NOUVEAUX ALGICIDES SELECTIFS DESTINES A LA LUTTE CONTRE LA CYANOCHLORONTA
  申请人：US AGRICULTURE

  公开号：WO2004060061A1

  公开（公告）日：2004-07-22

  Certain newly developed 9, 10-anthraquinone derivatives possess potent activity against O. perornata while possessing a sufficiently high level of solubility in water to make their activity against O. perornata viable. These compounds possess a high level of activity against O. perornata yet are relatively non-toxic to green algae and fishes. The compounds also possess a relatively short half-life. The compounds represent a new means to providing compounds possessing a high degree of selective activity against blue-green algae while being physiologically tolerated by catfish and green algae. The compounds provide a means for controlling blue-green algae in managed bodies of water that are destined for public use or consumption.