12b-methyl-8,11-dimethoxy-1H-benzo[6,7]phenanthro[10,1-bc]furan-6-(12bH)-one | 183727-69-7

• 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: 12b-methyl-8,11-dimethoxy-1H-benzo[6,7]phenanthro[10,1-bc]furan-6-(12bH)-one
• 英文别名: 5,8-Dimethoxy-1-methyl-14-oxapentacyclo[11.6.1.02,11.04,9.016,20]icosa-2,4,6,8,10,13(20),15,17-octaen-12-one
• CAS: 183727-69-7
• 化学式: C₂₂H₁₈O₄
• 分子量: 346.383
• InChiKey: UZODPGBHMLFVDR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 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：

  12b-methyl-8,11-dimethoxy-1H-benzo[6,7]phenanthro[10,1-bc]furan-6-(12bH)-one 在 palladium on activated charcoal ammonium cerium(IV) nitrate 、 氢气 作用下， 生成 齐斯托醌
  参考文献：
  名称：

  银盐对不对称的heck反应产生影响。（+）-异戊醌的催化不对称全合成

  摘要：

  使用芳基溴化物衍生物（4）的级联型不对称Heck反应（高达ee的63％和化学收率的39％（转化率的66％））已经实现了对（+）-对甲苯醌的对映选择性全合成。使用大量的银交换沸石导致ee和产率降低。这是银盐量对ee和产品收率的影响的第一个例子。

  DOI：

  10.1016/s0040-4020(98)00797-2
• 作为产物：
  描述：

  4,7-dimethoxybenzofuran 在 sodium 、 四氯苯醌 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 、 xylene 为溶剂， 反应 94.75h， 生成 12b-methyl-8,11-dimethoxy-1H-benzo[6,7]phenanthro[10,1-bc]furan-6-(12bH)-one
  参考文献：
  名称：

  Isobenzofurans and ortho-benzoquinone monoketals in syntheses of xestoquinone and its 9- and 10-methoxy derivatives

  摘要：

  Syntheses of (+/-)-xestoquinone, (+/-)-9-methoxyxestoquinone and (+/-)-10-methoxyxestoquinone are described. A convergent CD plus ABE plan using the appropriate isobenzofuran (CD) and naphthofuranone (ABE) has been implemented to provide these marine metabolites in overall yields of 18.3, 9.5 and 8.5%, respectively. The latter pair of compounds, previously evaluated as inhibitors of Topoisomerase II as an inseparable mixture, are now available separate and pure for the first time. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00938-8

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。
• Intramolecular Diels−Alder and Cope Reactions of <i>o</i>-Quinonoid Monoketals and Their Adducts:  Efficient Syntheses of (±)-Xestoquinone and Heterocycles Related to Viridin
  作者：Rina Carlini、Kerianne Higgs、Christina Older、Sab Randhawa、Russell Rodrigo

  DOI：10.1021/jo970394l

  日期：1997.4.1
• Silver salt effects on an asymmetric heck reaction. Catalytic asymmetric total synthesis of (+)-xestoquinone
  作者：Futoshi Miyazaki、Koichiro Uotsu、Masakatsu Shibasaki

  DOI：10.1016/s0040-4020(98)00797-2

  日期：1998.10

  An enantioselective total synthesis of (+)-xestoquinone has been achieved using a cascade-type asymmetric Heck reaction (in up to 63% ee and 39% chemical yield (66% conversion yield)) of the aryl bromide derivative (4). The use of a larger amount of silver exchanged zeolite resulted in a decrease in ee and yield. This is the first example of an effect of the amount of a silver salt on the ee and yield

  使用芳基溴化物衍生物（4）的级联型不对称Heck反应（高达ee的63％和化学收率的39％（转化率的66％））已经实现了对（+）-对甲苯醌的对映选择性全合成。使用大量的银交换沸石导致ee和产率降低。这是银盐量对ee和产品收率的影响的第一个例子。
• Isobenzofurans and ortho-benzoquinone monoketals in syntheses of xestoquinone and its 9- and 10-methoxy derivatives
  作者：Hamish S Sutherland、Kerianne C Higgs、Nicholas J Taylor、Russell Rodrigo

  DOI：10.1016/s0040-4020(00)00938-8

  日期：2001.1

  Syntheses of (+/-)-xestoquinone, (+/-)-9-methoxyxestoquinone and (+/-)-10-methoxyxestoquinone are described. A convergent CD plus ABE plan using the appropriate isobenzofuran (CD) and naphthofuranone (ABE) has been implemented to provide these marine metabolites in overall yields of 18.3, 9.5 and 8.5%, respectively. The latter pair of compounds, previously evaluated as inhibitors of Topoisomerase II as an inseparable mixture, are now available separate and pure for the first time. (C) 2000 Elsevier Science Ltd. All rights reserved.