1-羟基-5-甲氧基-9,10-蒽醌 | 52869-21-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 中文名称: 1-羟基-5-甲氧基-9,10-蒽醌
• 英文名称: 1-hydroxy-5-methoxy-9,10-anthraquinone
• 英文别名: 1-methoxy-5-hydroxy-9,10-anthraquinone；1-hydroxy-5-methoxyanthraquinone；1-hydroxy-5-methoxy-anthraquinone；1-Hydroxy-5-methoxy-anthrachinon；1-Hydroxy-5-methoxy-9,10-anthrachinon；1-hydroxy-5-methoxyanthracene-9,10-dione
• CAS: 52869-21-3
• 化学式: C₁₅H₁₀O₄
• 分子量: 254.242
• InChiKey: AFOIFPFVHYYDDG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2914690090

反应信息

• 作为反应物：
  描述：

  1-羟基-5-甲氧基-9,10-蒽醌 在 palladium on activated charcoal 吡啶 、 2,6-二甲基吡啶 、 4-二甲氨基吡啶 、 sodium hydroxide 、 sodium dithionite 、 phosphate buffer 、 二氯二茂铪 、 ammonium cerium(IV) nitrate 、 4 A molecular sieve 、 三氟化硼乙醚 、 氢气 、 氧气 、 silver perchlorate 、 乙酸酐 、 三溴化硼 、 sodium hydride 、 臭氧 、 三乙胺 、 N,N-二异丙基乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 乙硫醇 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， -78.0~25.0 ℃ 、101.33 kPa 条件下， 反应 17.59h， 生成 vineomycinone B2 methyl ester
  参考文献：
  名称：

  Convergent total synthesis of vineomycinone B2 methyl ester and its C(12)-epimer

  摘要：

  Total syntheses of vineomycinone B2 methyl ester (7) and its C(12)-epimer (epi-7) have been completed. The key reaction for construction of the aryl C-glycoside linkage is the O --> C-glycoside rearrangement starting from D-olivosyl fluoride derivative 11 and anthrol derivative 21, which provides the regio- and stereocontrolled formation of the aryl C-glycoside sector of the target. The combination of Cp2HfCl2-AgClO4 serves as a particularly efficient promoter for this reaction. An extensive model study for attaching the side chain is presented. The Lochmann-Schlosser base cleanly effects ortho metalation of anthracene derivatives 19 and 20. The metalated species can be trapped as stannyl derivatives, from which the corresponding aryllithium species are generated by using n-BuLi or preferably MeLi in toluene. These specific reaction conditions are necessary to suppress the abnormal reaction of RLi reagents at the C(9)/C(10)-positions of the anthracenes. Coupling of the side chain moiety was efficiently carried out by such metalation of anthracene derivative 25 followed by reaction with chiral aldehyde (S)-29. The chiral aldehyde was derived from enantiomerically pure acid (S)-37 obtained by enzymatic kinetic resolution. Deoxygenation of the benzylic alcohol function followed by several steps allowed the total ynthesis of 7. Starting from (R)-aldehyde 29, the same sequence of reactions accomplished the total synthesis of epi-7. The epi series of intermediates provided firm evidence for the stereochemical homogeneity of synthetic 7.

  DOI：

  10.1021/ja00018a041
• 作为产物：
  描述：

  2-Methoxyphenylmagnesium bromide 以 四氢呋喃 为溶剂， 生成 1-羟基-5-甲氧基-9,10-蒽醌
  参考文献：
  名称：

  A general, regiospecific synthesis of highly substituted quinones

  摘要：

  DOI：

  10.1021/jo00365a043

文献信息

• Selective demethylation of di- and tri-methoxyanthraquinones via aryloxydifluoroboron chelates. Synthesis of 4-hydroxy-1,5-dimethoxyanthraquinone and 1,4-dihydroxy-5-methoxyanthraquinone
  作者：Peter N. Preston、Thomas Winwick、John O. Morley

  DOI：10.1039/c39830000089

  日期：——

  Methoxyanthraquinone derivatives react with boron trifluoride–diethyl ether to give mono- and bis-difluoroboron chelates which, in methanol, are converted into hydroxyanthraquinones; an extension of this method is described for the synthesis of 2-hydroxy-2′,4,4′-trimethoxybenzophenone.

  甲氧基蒽醌衍生物与三氟化硼-乙醚反应，生成单-和双-二氟硼螯合物，在甲醇中转化为羟基蒽醌。描述了该方法的扩展，用于合成2-羟基-2'，4,4'-三甲氧基二苯甲酮。
• Polyhalogeno-allenes and -acetylenes. Part 16. Further 1,3-dipolar cycloadditions to perfluoropropadiene
  作者：Gordon B. Blackwell、Robert N. Haszeldine、David R. Taylor

  DOI：10.1039/p19830000001

  日期：——

  The nitrones PhCHN+(R)O–(R = Me, Et, PhCH2, and Ph) react rapidly with perfluoropropadiene to give the corresponding 2-R-4-difluoromethylene-5,5-difluoro-3-phenylisoxazolidines in good yield, although these isoxazolidines are unstable and decompose during catalytic hydrogenation. Perfluoropropadiene also reacts with diazophenylmethane and diazodiphenylmethane, giving 4-difluoromethylene-3,3-difluoro-5-phenyl-

  硝酮PhCH N +（R）O –（R = Me，Et，PhCH 2和Ph）与全氟丙二烯迅速反应，得到相应的2-R-4-二氟亚甲基-5,5-二氟-3-苯基异恶唑烷尽管这些异恶唑烷在催化氢化过程中不稳定并分解，但仍能得到收率。Perfluoropropadiene也与反应和diazophenylmethane diazodiphenylmethane，得到4-二氟亚甲基-3,3-二氟-5-苯基和5,5-二苯基- Δ 1-吡唑啉。二苯基吡唑啉在蒸馏时分解，得到3-二氟亚甲基-2,2-二氟二苯基环丙烷。这些偶极环加成的区域专一性是与前沿轨道理论相关的。苯甲酰重氮苯基甲烷在与全氟丙二烯的缓慢反应中分解，并且分离出的唯一加合物是3-二氟亚甲基-2,2-二氟-4,5-二苯基二氢呋喃。重氮二苯基甲烷与全氟丙炔反应，生成1：1的加合物，据认为是5-氟-3,3-二苯基-4-三氟甲基-3 H-吡唑。
• Experiments Directed Towards the Synthesis of Anthracyclinones. XXVI. The Preparation of Chiral Intermediates for Anthracyclinone Synthesis
  作者：DA Beauregard、RC Cambie、PC Dansted、PS Rutledge、PD Woodgate

  DOI：10.1071/ch9950669

  日期：——

  (2′R)-1,5-Dimethoxy-2(2′-methyloxiran-2′-ylmethyl) anthraquinone (8), an intermediate for the synthesis of fridamycin E, has been prepared enantioselectively via the diol (15). The diol (15) was prepared in high yield by asymmetric cis-hydroxylation of the alkene (11). The analogous diol (22), a vineomycinone B2 precursor, was also prepared.

  (2′R)-1,5-二甲氧基-2(2′-甲基环氧乙烷-2′-基甲基)蒽醌(8)是合成弗达霉素 E 的中间体，通过二元醇(15)对映选择性地制备得到。二元醇 (15) 是通过烯烃 (11) 的不对称顺式羟化反应以高产率制备的。此外，还制备出了类似的二元醇 (22)，这是一种藤黄霉素酮 B2 的前体。
• Approaches to the regiospecific synthesis of Anthracycline antibiotics
  作者：Jack E. Baldwin、Algis J. Rajeckas

  DOI：10.1016/0040-4020(82)80196-8

  日期：1982.1

  Synthetic approaches to anthracycline antibiotics were studied through the use of Claisen rearrangements on 1-methallyloxy-5-methoxyantraquinone (9) which required reducing conditions to proceed through a hydroquinone intermediate in situ. 1-(2′-Methylene-4′-pentenoxy)-5-methoxyanthraquinone (13) underwent a similar reductive rearrangement but also produced a spiro compound 16 as a result of an ene

  蒽环类抗生素的合成方法已通过在1-甲基烯丙氧基-5-甲氧基蒽醌（9）上使用克莱森重排进行了研究，该方法需要还原条件才能原位通过对苯二酚中间体。1-（2'-亚甲基-4'-戊烯氧基）-5-甲氧基蒽醌（13）进行了类似的还原重排，但由于苯酚和侧链双键之间的烯键反应，还产生了螺环化合物16。1-羟基-2-甲基-5-甲氧基蒽醌（11）不能被氧化为奎尼沙林17。1-羟基-2-甲基-5,9,10-三甲氧基蒽（21）在C-2处氧化偶联至二聚体。二聚体23与重氮甲烷反应形成1,3-偶极加合物24。
• Synthesis of - and -fridamycin E
  作者：Karsten Krohn、Wolfgang Baltus

  DOI：10.1016/s0040-4020(01)85091-2

  日期：1988.1

  Racemic fridamycin E (-1) was synthesized in two ways: 1. Addition of lithium -butyl acetate to ketone 15 followed by ether and ester cleavage to -1; 2. Grignard reaction of allylmagnesium bromide with 15 to -18 and subsequent ozonolysis, oxidation, methylation, ester and ether cleavage. The enantiomer -18 was obtained by Marschalk reaction of 7 with the chiral building block 20 derived from (S)-lactic

  外消旋fridamycin E（-1）的合成方法有两种：1.将乙酸丁酯锂添加到酮15中，然后将醚和酯裂解为-1。2.烯丙基溴化镁与15至-18的格氏反应，然后进行臭氧分解，氧化，甲基化，酯和醚裂解。对映体-18通过7与来自（S）-乳酸的手性结构单元20的Marschalk反应获得。类似的反应序列将-18转化为-1，从而证明天然fridamycin E具有（R）-构型。