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

• Total Synthesis of (+)-Xestoquinone Using an Asymmetric Palladium-Catalyzed Polyene Cyclization
  作者：Shawn P. Maddaford、Neil G. Andersen、Walter A. Cristofoli、Brian A. Keay

  DOI：10.1021/ja960807k

  日期：1996.1.1

  The first total asymmetric synthesis of (+)-xestoquinone (1) has been accomplished in 68% ee by a palladium(0)-catalyzed polyene cyclization of naphthyl triflate 44 using (S)-(+)-BINAP as the chiral ligand. Attempts at an asymmetric polyene cyclization using the corresponding naphthyl bromide 41 gave poor enantioselectivities even in the presence of silver salts, thus exemplifying the effect of the

  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。
• 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：——
• Total synthesis and absolute stereochemistry of (+)-xestoquinone and xestoquinol
  作者：Nobuyuki Harada、Tatsuo Sugioka、Hisashi Uda、Takeo Kuriki

  DOI：10.1021/jo00297a035

  日期：1990.5