nordihydrolapachenol | 18865-37-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: nordihydrolapachenol
• 英文别名: 2,2-Dimethyl-3,4-dihydrobenzo[h]chromen-6-ol；2,2-dimethyl-3,4-dihydrobenzo[h]chromen-6-ol
• CAS: 18865-37-7
• 化学式: C₁₅H₁₆O₂
• 分子量: 228.291
• InChiKey: NLGGHLCYGVGWMW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  nordihydrolapachenol 生成 6-acetoxy-2,2-dimethyl-5-morpholin-4-ylmethyl-3,4-dihydro-2H-benzo[h]chromene
  参考文献：
  名称：

  Synthesis of Methyl Substituted Chromanol. An Analogue of Vitamin K

  摘要：

  检查 2,2-二甲基-3,4-二氢-2H-苯并[h]色烯-6-醇 (1) 的甲基化，生成 2,2,3-三甲基-3,4-二氢-2H-苯并[ h]苯并六氢酚 (2)。化合物2是通过曼尼希反应和曼尼希碱的氢化裂解制备的，曼尼希碱是与三种胺反应得到的。 1的氯甲基化定量地得到萘醌甲基化物的二聚体。

  DOI：

  10.1246/bcsj.52.1143
• 作为产物：
  描述：

  1,4-萘醌 在 甲酸 、 sodium dithionite 、 5%-palladium/activated carbon 、 氢气 、 维生素 C 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成 nordihydrolapachenol
  参考文献：
  名称：

  取代苯并[h]色原醇的合成及自由基清除活性

  摘要：

  Benzo[h]chromanols, which possess a tocopherol moiety, have been reported to exhibit potent antioxidant activity. Several benzo[h]chromanols with various substituents (nitro, chloro, bromo, methyl, or amino groups at the position ortho to the phenolic OH group) were synthesized, and the second-order rate constants (k) of their reaction with the galvinoxyl radical were determined. The introduction of electron-withdrawing bromo, chloro and nitro groups decreased the activity, and the activity correlated well with the substituent effect. ortho-Aminobenzo[h]chromanol showed the highest radical scavenging activity among the compounds synthesized.

  DOI：

  10.3987/com-17-13671

文献信息

• Synthesis, Characterization, and Antileukemic Properties of Naphthoquinone Derivatives of Lawsone
  作者：Ryuta Inagaki、Masayuki Ninomiya、Kaori Tanaka、Mamoru Koketsu

  DOI：10.1002/cmdc.201500189

  日期：2015.8

  Naphthoquinones are considered privileged structures for anticancer drug molecules. The Heck reaction of 2‐hydroxy‐1,4‐naphthoquinone (lawsone) with 1‐bromo‐3‐methyl‐2‐butene offered easy access to lapachol. Several naturally occurring linear and angular heterocyclic quinoids (α‐lapachone, β‐lapachone, dunnione, and related analogues) were prepared from lapachol. Furthermore, we demonstrated that the

  萘醌被认为是抗癌药物分子的特殊结构。2-羟基-1,4-萘醌（劳松）与 1-溴-3-甲基-2-丁烯的赫克反应提供了容易获得拉帕酚的途径。几种天然存在的线性和角杂环醌类化合物（α-lapachone、β-lapachone、dunnione 和相关类似物）由拉帕酚制备。此外，我们证明合成萘醌可抑制人白血病 HL-60 细胞的细胞增殖。特别是，角型衍生物被发现具有中等的细胞毒性并提高细胞内谷胱甘肽二硫化物（GSSG）的水平。我们的工作突出了天然存在的角系列萘醌作为抗白血病药物的巨大潜力。
• Unexpected transformation of quinones to spirolactones and to naturally occurring naphthalenic compounds
  作者：Eufrânio N. da Silva Júnior、Carlos A. de Simone、Adolfo C.B. de Souza、Cleverson N. Pinto、Tiago T. Guimarães、Maria do Carmo F.R. Pinto、Antônio V. Pinto

  DOI：10.1016/j.tetlet.2009.01.058

  日期：2009.4

  natural quinones of the lapachol group have been used as starting points for the preparation of several bioactive heterocyclic compounds. Herein, we announce that lapachones, derivatives of lapachol, under certain conditions in the presence of inorganic reagents give unexpected products, spirolactones and naphthalenic derivatives, nordihydrolapachenone and tetrahydrotectol, both naturally occurring compounds

  在最近几年中，拉帕酚基的天然醌已被用作制备几种生物活性杂环化合物的起点。在此，我们宣布，在某些条件下，在无机试剂存在的情况下，拉帕胆酚的衍生物拉帕酮会产生意想不到的产物，螺内酯和萘衍生物，降二氢拉帕酮和四氢ectol，这两种化合物都是天然存在的化合物。通过X射线分析鉴定了诺地拉帕金酮。拉帕酚本身也可以转化为四氢ectol。
• Construction of Functionalized <i>ortho</i>‐Naphthoquinone Methides via Site‐Selective Ring Opening of 1‐Siloxy‐1,4‐epoxy‐1,4‐dihydronaphthalenes
  作者：Takaaki Aijima、Shinsuke Komagawa、Shuji Akai、Yoshinari Sawama

  DOI：10.1002/adsc.202300968

  日期：2023.11.21

  underwent automatic site-selective ring opening because of the synergetic effect of the steric strain of the 1,4-epoxy moiety and the electron-donating ability of the siloxy group on the acetal structure to afford the precursors of ortho-naphthoquinone methides (o-NQMs). Subsequent Lewis acid-facilitated o-NQM formation and annulation with olefins afforded multi-fused heterocycles. Notably, the consecutive

  由苯炔和呋喃生成的1-甲硅烷氧基-4-(苄氧基)甲基-1,4-环氧-1,4-二氢萘由于1,4空间张力的协同作用而自动进行位点选择性开环-环氧部分和缩醛结构上甲硅烷氧基的给电子能力，提供邻萘醌甲基化物（o -NQMs）的前体。随后路易斯酸促进邻-NQM 形成并与烯烃成环，得到多稠合杂环。值得注意的是，rubioncolin B 的连续六环骨架是通过萘并呋喃衍生物的溶剂依赖性区域选择性成环构建的。
• Synthesis and Radical Scavenging Activity of Substituted Benzo[h]chromanols
  作者：Keiko Inami、Yuta Okayama、Masanori Harada、Mine Morita、Masataka Mochizuki

  DOI：10.3987/com-17-13671

  日期：——

  Benzo[h]chromanols, which possess a tocopherol moiety, have been reported to exhibit potent antioxidant activity. Several benzo[h]chromanols with various substituents (nitro, chloro, bromo, methyl, or amino groups at the position ortho to the phenolic OH group) were synthesized, and the second-order rate constants (k) of their reaction with the galvinoxyl radical were determined. The introduction of electron-withdrawing bromo, chloro and nitro groups decreased the activity, and the activity correlated well with the substituent effect. ortho-Aminobenzo[h]chromanol showed the highest radical scavenging activity among the compounds synthesized.
• Synthesis of Methyl Substituted Chromanol. An Analogue of Vitamin K
  作者：Kazuhiro Maruyama、Takamasa Tobimatsu、Yoshinori Naruta

  DOI：10.1246/bcsj.52.1143

  日期：1979.4

  Methylation of 2,2-dimethyl-3,4-dihydro-2H-benzo[h]chromen-6-ol (1) is examined to yield 2,2,3-trimethyl-3,4-dihidro-2H-benzo[h]chromen-6-ol (2). The compound 2 is prepared by Mannich reaction followed by hydrogenative cleavage of the Mannich bases, which are obtained in the reaction with three kinds of amine. Chloromethylation of 1 quantitatively gave a dimer of naphthoquinone methide.

  检查 2,2-二甲基-3,4-二氢-2H-苯并[h]色烯-6-醇 (1) 的甲基化，生成 2,2,3-三甲基-3,4-二氢-2H-苯并[ h]苯并六氢酚 (2)。化合物2是通过曼尼希反应和曼尼希碱的氢化裂解制备的，曼尼希碱是与三种胺反应得到的。 1的氯甲基化定量地得到萘醌甲基化物的二聚体。