2-溴-8-羟基-6-甲基萘-1,4-二酮 | 161811-59-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 2-溴-8-羟基-6-甲基萘-1,4-二酮
• 英文名称: 3-bromo-7-methyljuglone
• 英文别名: 2-bromo-8-hydroxy-6-methylnaphthoquinone；2-bromo-8-hydroxy-6-methyl-1,4-naphthoquinone；2-bromo-8-hydroxy-6-methylnaphthalene-1,4-dione
• CAS: 161811-59-2
• 化学式: C₁₁H₇BrO₃
• 分子量: 267.079
• InChiKey: JTXZJKMQLWGQLZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-溴-8-羟基-6-甲基萘-1,4-二酮 在 20 % Pd(OH)2/C 、 氢气 、 copper diacetate 、 potassium carbonate 、 silver(l) oxide 作用下， 以 二氯甲烷 、 乙酸乙酯 、 乙腈 为溶剂， 反应 96.0h， 生成 11-hydroxy-1,9-dimethyl-6H-naphtho[2',3':4,5]furo[3,2-c]chromene-6,7,12-trione
  参考文献：
  名称：

  合成的报告的结构crassiflorone，一种从非洲乌木Diospyros crassiflora分离出的天然醌和区域异构的五环呋喃香豆素萘醌

  摘要：

  描述了报道的天然产物crassiflorone（呋喃香豆素萘醌）的结构合成。关键步骤是形成狄尔斯-阿尔德反应2-溴-8-羟基-6-甲基萘醌然后进行O保护和铜（II）介导的偶联4-羟基-5-甲基香豆素建立五环骨架，其结构已通过X射线晶体学明确证实。由于合成材料的光谱数据与天然产物的光谱数据不匹配，因此另外三个区域异构体呋喃香豆素萘醌是通过铜（II）介导的4-羟基-5-或8-甲基香豆素与5-苄氧基-2-溴-7-甲基-或8-苄氧基-2-溴-6-甲基-1的偶联而制备的， 4-萘醌。再次，光谱数据与天然物质的光谱数据不匹配，因此，卡西花酮的真实结构仍是未知的。

  DOI：

  10.1039/c0ob01231a
• 作为产物：
  描述：

  2,6-二溴对苯醌 在 silica gel 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 24.0h， 生成 2-溴-8-羟基-6-甲基萘-1,4-二酮
  参考文献：
  名称：

  合成的报告的结构crassiflorone，一种从非洲乌木Diospyros crassiflora分离出的天然醌和区域异构的五环呋喃香豆素萘醌

  摘要：

  描述了报道的天然产物crassiflorone（呋喃香豆素萘醌）的结构合成。关键步骤是形成狄尔斯-阿尔德反应2-溴-8-羟基-6-甲基萘醌然后进行O保护和铜（II）介导的偶联4-羟基-5-甲基香豆素建立五环骨架，其结构已通过X射线晶体学明确证实。由于合成材料的光谱数据与天然产物的光谱数据不匹配，因此另外三个区域异构体呋喃香豆素萘醌是通过铜（II）介导的4-羟基-5-或8-甲基香豆素与5-苄氧基-2-溴-7-甲基-或8-苄氧基-2-溴-6-甲基-1的偶联而制备的， 4-萘醌。再次，光谱数据与天然物质的光谱数据不匹配，因此，卡西花酮的真实结构仍是未知的。

  DOI：

  10.1039/c0ob01231a

文献信息

• Synthesis of the Reported Structure of Crassiflorone, a Pentacyclic Naphthoquinone Isolated from the African Ebony Diospyros crassiflora
  作者：Christopher Moody、Jalindar Padwal、William Lewis

  DOI：10.1055/s-0029-1218578

  日期：2010.3

  A short synthesis of the furocoumarin naphthoquinone structure reported for the natural product crassiflorone is descnbed, in which the key steps are a Diels-Alder reaction to form 2-bromo-8-hydroxy-6-methylnaphthoquinone, followed by O-protection and copper(II)-mediated coupling to 4-hydroxy-5-methylcoumarin to establish the pentacyclic framework.

  描述了天然产物紫花酮的呋喃香豆素萘醌结构的简短合成，其中关键步骤是狄尔斯-阿尔德反应形成 2-溴-8-羟基-6-甲基萘醌，然后是 O-保护和铜（ II) 介导的与 4-羟基-5-甲基香豆素的偶联以建立五环框架。
• Convergent total synthesis of the michellamines
  作者：T.Ross Kelly、Alberto Garcia、Fengrui Lang、John J. Walsh、K.Vijaya Bhaskar、Michael R. Boyd、Roland Götz、Paul A. Keller、Rainer Walter、Gerhard Bringmann

  DOI：10.1016/s0040-4039(00)78358-4

  日期：1994.10

  The total synthesis of both michellamine A (1a) and B (1b), by consecutive construction first of the inner (non-stereogenic) axis and subsequently the two outer (stereogenic) axes in a highly convergent manner, is described. The michellamines are of considerable interest due to their pronounced anti-HIV activity.

  描述了先通过内（非立体异构）轴，然后是两个外（立体异构）轴以高度收敛的方式连续构建而完成的米奇拉明A（1a）和B（1b）的总合成。由于其显着的抗HIV活性，米其敏胺引起了人们的极大兴趣。
• A Convergent Total Synthesis of the Michellamines
  作者：Gerhard Bringmann、Roland Götz、Paul A. Keller、Rainer Walter、Michael R. Boyd、Fengrui Lang、Alberto Garcia、John J. Walsh、Imanol Tellitu、K. Vijaya Bhaskar、T. Ross Kelly

  DOI：10.1021/jo971495m

  日期：1998.2.1

  A convergent total synthesis of the anti-HIV michellamines (1) is described. The tetraaryl skeleton of the michellamines mas constructed by formation first of the inner (nonstereogenic) biaryl axis and subsequently of the two other (stereogenic) axes in a highly convergent manner. The key transformation features a double Suzuki-type cross-coupling reaction between binaphthalene ditriflate 26 and isoquinolineboronic acid 35. Ditriflate 26 is synthesized in six steps starting from diene 6 and 2,6-dibromobenzoquinone (9) in 21% overall yield. For large scale production of 26, a substantially shortened version of an existing procedure for the preparation of bisnaphthoquinone 13 was also developed, which allows far the preparation of 13 from benzoquinone and diene 6 in five steps and 67% overall yield. Binaphthoquinone 13 was subsequently converted into ditriflate 26 in three steps and 67% overall yield, By the described synthetic strategy, michellamines A (1a) and B (1b) are produced (1a:1b = 1:2.5) in 24.6% overall yield from diene 6. Curiously, none of the nonnaturally occurring atropoisomer 1c is formed.
• Total Synthesis of the Antitumor–Antitubercular 2,6′-Bijuglone Natural Product Diospyrin and Its 3,6′-Isomer
  作者：Glenn A. Pullella、Daniel Vuong、Ernest Lacey、Matthew J. Piggott

  DOI：10.1021/acs.jnatprod.0c00800

  日期：2020.12.24

  The 2,6'-bijuglone natural product diospyrin and its unnatural 3,6'-isomer idospyrin have been synthesized in seven steps each from N,N-diethylsenecioamide in overall yields of 12% and 13%, respectively. The syntheses diverge from ramentaceone (7-methyljuglone) and include a key Suzuki-Miyaura cross-coupling. Diospyrin, idospyrin, and several synthetic precursors exhibit potent and selective cytotoxicity to the murine myeloma NS-1 cell line over neonatal foreskin cells.
• Synthesis of the reported structure of crassiflorone, a naturally occurring quinone isolated from the African ebony Diospyros crassiflora, and regioisomeric pentacyclic furocoumarin naphthoquinones
  作者：Jalindar Padwal、William Lewis、Christopher J. Moody

  DOI：10.1039/c0ob01231a

  日期：——

  The key steps are a Diels–Alder reaction to form 2-bromo-8-hydroxy-6-methylnaphthoquinone, followed by O-protection and copper(II) mediated coupling to 4-hydroxy-5-methylcoumarin to establish the pentacyclic framework whose structure was unambiguously confirmed by X-ray crystallography. Since the spectroscopic data of the synthetic material did not match those reported for the natural product, three

  描述了报道的天然产物crassiflorone（呋喃香豆素萘醌）的结构合成。关键步骤是形成狄尔斯-阿尔德反应2-溴-8-羟基-6-甲基萘醌然后进行O保护和铜（II）介导的偶联4-羟基-5-甲基香豆素建立五环骨架，其结构已通过X射线晶体学明确证实。由于合成材料的光谱数据与天然产物的光谱数据不匹配，因此另外三个区域异构体呋喃香豆素萘醌是通过铜（II）介导的4-羟基-5-或8-甲基香豆素与5-苄氧基-2-溴-7-甲基-或8-苄氧基-2-溴-6-甲基-1的偶联而制备的， 4-萘醌。再次，光谱数据与天然物质的光谱数据不匹配，因此，卡西花酮的真实结构仍是未知的。