9-Hydroxy-8-methoxy-3-methyl-3,4-dihydro-2H-anthracen-1-one | 79482-35-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 9-Hydroxy-8-methoxy-3-methyl-3,4-dihydro-2H-anthracen-1-one
• CAS: 79482-35-2
• 化学式: C₁₆H₁₆O₃
• 分子量: 256.301
• InChiKey: TZBHYQVXTUVNFA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  9-Hydroxy-8-methoxy-3-methyl-3,4-dihydro-2H-anthracen-1-one 在 calcium sulfate 、 lithium aluminium tetrahydride 、 三溴化硼 、 四丁基碘化铵 、 sodium hydride 、 scandium tris(trifluoromethanesulfonate) 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 二甲基亚砜 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 41.17h， 生成
  参考文献：
  名称：

  吡咯霉素的合成2：Saptomycin B的总合成和结构分配

  摘要：

  据报道，简明的，高度收敛的全合成的Saptomycin B，是抗肿瘤抗生素的pluramycin类成员。通过10次合成操作，从15个产率的15％收率中，从四个构件（三环平台，两个糖和一个炔基）组装了目标化合物。关键步骤包括在三轮车上选择性选择性地安装两个氨基糖（L- vancosamine和D- angolosamine），以及通过羟醛反应有效地构建四环骨架，然后形成吡喃酮。在C14未知配置被分配了作为[R 。

  DOI：

  10.1002/anie.201308017
• 作为产物：
  描述：

  3,5-dimethyl-2-(2-methoxybenzoyl)-cyclohex-2-enone 以7%的产率得到
  参考文献：
  名称：

  TAMURA YASUMITSU; WADA AKIMORI; OKUYAMA SHICENIRO; FUKUMORI SATOSHI; HAYA+, CHEM. AND PHARM. BULL., 1981, 29, NO 5, 1312-1320

  摘要：

  DOI：

文献信息

• Toward Pluramycins with Epoxy Side Chain: Syntheses of Kidamycinone and Epoxykidamycinone (Saptomycinone H)
  作者：Yoshio Ando、Yoshihiko Maezawa、Jun Shimura、Kei Kitamura、Takashi Matsumoto、Keisuke Suzuki

  DOI：10.1002/asia.201901807

  日期：2020.3.16

  For exploring general routes to the pluramycin-class of antibiotics, including congeners with epoxide-bearing side chains, syntheses of kidamycinone and its epoxide (epoxykidamycinone) have been achieved. At the stage of the A-ring cyclization with alkene-bearing side chain, the desired 6-endo product was obtained as a major compound, although the corresponding undesired 5-exo product was also formed

  为了探索通向普鲁霉素类抗生素（包括带有环氧化物侧链的同类物）的一般途径，已合成了Kidamycinone及其环氧化合物（epoxykidamycinone）。在带有含烯烃的侧链的A环环化阶段，虽然还形成了相应的不希望有的5-exo产物，但仍获得了作为主要化合物的期望的6-endo产物。
• Hydroxylamine-Mediated Anthrapyranone Formation, Solving 5-exo/6-endo Issue toward Synthesis of Pluramycin-Class Antibiotics
  作者：Jun Shimura、Yoshio Ando、Keisuke Suzuki

  DOI：10.1021/acs.orglett.9b04127

  日期：2020.1.3

  In our synthetic study on pluramycin-class antibiotics, an unexpected issue arose, i.e., unfavorable regioselectivity of 5-exo rather than 6-endo cyclization to form the pyranone ring. The issue was solved by an addition-elimination process of a phenol-ynone substrate. AZADOL was specifically effective, enabling the first synthesis of saptomycinone H.
• Tamura, Yasumitsu; Wada, Akimori; Okuyama, Shigehiro, Chemical and pharmaceutical bulletin, 1981, vol. 29, # 5, p. 1312 - 1320
  作者：Tamura, Yasumitsu、Wada, Akimori、Okuyama, Shigehiro、Fukumori, Satoshi、Hayashi, Yoko、et al.

  DOI：——

  日期：——
• Toward the Pluramycins: Route Exploration from Dihydroxyanthrone Tricyclic Platform to an Aglycon, Saptomycinone B
  作者：Keisuke Suzuki、Takashi Matsumoto、Kei Kitamura、Yoshio Ando、Yoshihiko Maezawa

  DOI：10.3987/com-14-s(k)106

  日期：——

  In connection with the total synthesis of the pluramycin-class antibiotics, we recently found dihydroxyanthrone derivatives to be suitable platforms for the installation of bis-C-glycosides. As a basis for the total synthesis, we explored viable routes to construct the characteristic tetracyclic skeleton. By setting saptomycinone B (5) as a model target, anthrone 6 was combined with the side chain moiety to access key intermediate 9, from which two viable routes have been developed. One of the routes has been exploited in the realization of our recent total synthesis of saptomycin B (4).