xestoquinol dimethyl ether | 127232-73-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: xestoquinol dimethyl ether
• 英文别名: (1S)-5,8-dimethoxy-1-methyl-14-oxapentacyclo[11.6.1.02,11.04,9.016,20]icosa-2,4,6,8,10,13(20),15-heptaen-12-one
• CAS: 127232-73-9
• 化学式: C₂₂H₂₀O₄
• 分子量: 348.398
• InChiKey: IPVMJHCYMXESQI-QFIPXVFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  48.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  xestoquinol dimethyl ether 在 ammonium cerium(IV) nitrate 作用下， 以 乙腈 为溶剂， 反应 0.17h， 生成 齐斯托醌
  参考文献：
  名称：

  使用不对称钯催化多烯环化全合成 (+)-Xestoquinone

  摘要：

  使用 (S)-(+)-BINAP 作为手性配体，通过钯 (0) 催化的三氟甲磺酸萘酯 44 的多烯环化反应以 68% ee 完成了 (+)-xestoquinone (1) 的首次全不对称合成。即使在银盐存在的情况下，使用相应的萘基溴 41 进行不对称多烯环化的尝试也给出了较差的对映选择性，因此举例说明了钯的配位状态对对映选择性的影响。还描述了一种在七元环醚前体上使用 [1,2]-Wittig 重排制备 6,7-二氢异苯并呋喃的新方法。

  DOI：

  10.1021/ja960807k
• 作为产物：
  描述：

  O-<(4aR,5S,6S,8aR)-3,4,4a,5,6,7,8,8a-octahydro-5-<(methoxymethoxy)methyl>-8a-methyl-1(2H)-oxonaphthalen-6-yl>S-methyl dithiocarbonate ethylene acetal 在 3,5-二甲基吡唑 、 chromium(VI) oxide 、 盐酸 、 manganese(IV) oxide 、 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile 、 potassium tert-butylate 、 甲基锂 、 氧气 、 三正丁基氢锡 、 对甲苯磺酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 乙醇 、 二氯甲烷 、 水 、 丙酮 、 甲苯 、 叔丁醇 、 苯 为溶剂， 反应 46.5h， 生成 xestoquinol dimethyl ether
  参考文献：
  名称：

  Total synthesis and absolute stereochemistry of (+)-xestoquinone and xestoquinol

  摘要：

  DOI：

  10.1021/jo00297a035

文献信息

• Asymmetric total synthesis of (+)-xestoquinone and (+)-adociaquinones A and B
  作者：Xiao-Long Lu、Yuanyou Qiu、Baochao Yang、Haibing He、Shuanhu Gao

  DOI：10.1039/d0sc07089k

  日期：——

  The asymmetric total synthesis of (+)-xestoquinone and (+)-adociaquinones A and B was achieved in 6–7 steps using an easily accessible meso-cyclohexadienone derivative. The [6,6]-bicyclic decalin B–C ring and the all-carbon quaternary stereocenter at C-6 were prepared via a desymmetric intramolecular Michael reaction with up to 97% ee. The naphthalene diol D–E ring was constructed through a sequence

  (+)-xestoquinone 和 (+)-adociaquinones A 和 B 的不对称全合成是使用易于获得的内消旋环己二烯酮衍生物通过 6-7 个步骤实现的。 [6,6]-双环十氢萘 B-C 环和 C-6 处的全碳四元立构中心通过不对称分子内 Michael 反应制备，ee 高达 97%。萘二醇 D-E 环是通过一系列 Ti(Oi-Pr) 4促进的光烯醇化/Diels-Alder、脱水和芳构化反应构建的。这种不对称策略提供了一种可扩展的途径来制备目标分子及其衍生物以用于进一步的生物学研究。
• Total Synthesis, Absolute Configuration, and Later Isolation of (-)-Prehalenaquinone, a Putative Biosynthetic Precursor to the Marine Natural Products: Halenaquinone and Xestoquinone
  作者：Nobuyuki Harada、Tatsuo Sugioka、Hisashi Uda、Takeo Kuriki、Motomasa Kobayashi、Isao Kitagawa

  DOI：10.1021/jo00101a019

  日期：1994.11

  As part of the total syntheses of halenaquinone (1) and xestoquinone (4), cardiotonic and cytotoxic marine natural products isolated from tropical marine sponges, we have found a new reaction pathway of the DMSO/DCC/PPTS or PTFA reagent that is useful for constructing a dihydrofuran ring system. By application of the reaction, we prepared synthetic intermediate (3S,3aS,12bS)-(-)-8 with a dihydrofuran ring moiety, from which both (+)-halenaquinone (1) and (+)-xestoquinone (4) were synthesized; DMSO/DCC/PPTS oxidation of dihydrofuran-alcohol 8 led to 1, while acid-catalyzed dehydration led to 4. The mechanism of the new DMSO/DCC/PPTS or PTFA reaction was clarified by use of O-18 labeling. We postulated that these synthetic routes might simulate the biosyntheses of 1 and 4 in marine sponges, and putative biosynthetic precursor (3S,3aS,12bS)-(-)-7, named prehalenaquinone, was synthesized. Later, we succeeded in isolating (-)-7 from an Okinawan marine sponge, Xestospongia sapra.
• Synthesis of biotinylated xestoquinone that retains inhibitory activity against Ca2+ ATPase of skeletal muscle myosin
  作者：Mitsuhiro Nakamura、Takahiko Kakuda、Yuichi Oba、Makoto Ojika、Hideshi Nakamura

  DOI：10.1016/s0968-0896(03)00276-1

  日期：2003.7

  Xestoquinone isolated from a marine sponge binds to skeletal muscle myosin and inhibits its Ca2+ ATPase activity. In this study, we first examined xestoquinone and its analogues to assess the relationships between structure and myosin Ca2+ ATPase inhibitory activity. On the basis of the resultant data, we then designed a biotinylated xestoquinone analogue. Xestoquinone and its analogues were derived from extracts of the marine sponge Xestospongia sapra. Four xestoquinone analogues with a quinone structure significantly inhibited Ca2+ ATPase activity. In contrast, four xestoquinone analogues in which the quinone structure was converted to a quinol dimethyl ether did not inhibit Ca2+ ATPase activity. This suggests that the quinone moiety is essential for inhibitory activity. Then, we synthesized a biotinylated xestoquinone in which a biotin tag was introduced to a site far from the quinone moiety, and this molecule exhibited stronger inhibitory activity than that of xestoquinone. This biotinylated xestoquinone could be useful as a probe in studies of the xestoquinone-myosin binding mode. (C) 2003 Elsevier Science Ltd. All rights reserved.
• HARADA, NOBUYUKI;SUGIOKA, TATSUO;UDA, HISASHI;KURIKI, TAKEO, J. ORG. CHEM., 55,(1990) N0, C. 3158-3163
  作者：HARADA, NOBUYUKI、SUGIOKA, TATSUO、UDA, HISASHI、KURIKI, TAKEO

  DOI：——

  日期：——