2-hydroxy-3-(3-phenylpropyl)naphthalene-1,4-dione | 22799-73-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-hydroxy-3-(3-phenylpropyl)naphthalene-1,4-dione
• 英文别名: 2-hydroxy-3-(3-phenylpropyl)-1,4-naphthoquinone；2-hydroxy-3-(3-phenyl-propyl)-[1,4]naphthoquinone；2-Hydroxy-3-(3-phenyl-propyl)-[1,4]naphthochinon
• CAS: 22799-73-1
• 化学式: C₁₉H₁₆O₃
• 分子量: 292.334
• InChiKey: MNSCJLMXWJJSLM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  54.37
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-硝基-1-丙烯 、 2-hydroxy-3-(3-phenylpropyl)naphthalene-1,4-dione 在 N-[3,5-双(三氟甲基)苯基]-N'-[(8a,9S)-6'-甲氧基-9-金鸡宁]硫脲 作用下， 以 甲苯 为溶剂， 反应 0.5h， 生成 (5R,6R,8S)-6-ethyl-5-hydroxy-8-methyl-6-nitro-7,8-dihydro-5H-5,8-methanobenzo[7]annulene-9,10(6H)-dione
  参考文献：
  名称：

  百万分率水平的催化 [3+2]-环化，用于不对称合成甲烷苯并 [7] 环烯

  摘要：

  甲烷苯并[7]环烯。[3+2]-环化的百万分之一催化剂负载。报道了一种前所未有的 ppm 级催化不对称 [3+2]-环化 3-烷基-劳森酮与硝基乙烯。它是一种有效、可持续、催化不对称环化反应，用于合成手性甲烷苯并 [7] 环烯，这是许多抗生素的一部分。

  DOI：

  10.1002/chem.202103254
• 作为产物：
  描述：

  4-苯基丁酰氯 在 sodium peroxide 、 水 、 正戊烷 作用下， 生成 2-hydroxy-3-(3-phenylpropyl)naphthalene-1,4-dione
  参考文献：
  名称：

  Fieser et al., Journal of the American Chemical Society, 1948, vol. 70, p. 3177

  摘要：

  DOI：

文献信息

• Organocatalytic Asymmetric Formal [3+2] Cycloaddition as a Versatile Platform to Access Methanobenzo[7]annulenes
  作者：Dhevalapally B. Ramachary、Mohammed Anif Pasha、Guguloth Thirupathi

  DOI：10.1002/anie.201706557

  日期：2017.10.9

  and structurally important methanobenzo[7]annulenes were synthesized in very good yields with excellent enantio‐ and diastereoselectivities through an unprecedented organocatalytic formal [3+2] cycloaddition from readily available 2‐alkyl‐3‐hydroxynaphthalene‐1,4‐diones and alkyl vinyl ketones.

  药学上和结构上重要的甲氧基苯并[7]环戊烯可通过空前的2-烷基-3-羟基萘-1,4-二酮和烷基的空前的有机催化形式[3 + 2]环加成反应以良好的对映异构和非对映选择性很好地合成。乙烯基酮。
• On the Oxidation of 2-Hydroxy-1,4-naphthoquinone Derivatives with Alkaline Potassium Permanganate^1,2
  作者：Samuel C. Hooker

  DOI：10.1021/ja01298a030

  日期：1936.7
• Design, Synthesis, and Biological Testing of Novel Naphthoquinones as Substrate-Based Inhibitors of the Quinol/Fumarate Reductase from <i>Wolinella succinogenes</i>
  作者：Hamid Reza Nasiri、M. Gregor Madej、Robin Panisch、Michael Lafontaine、Jan W. Bats、C. Roy D. Lancaster、Harald Schwalbe

  DOI：10.1021/jm400978u

  日期：2013.12.12

  Novel naphthoquinones were designed, synthesized, and tested as substrate-based inhibitors against the membrane-embedded protein quinol/fumarate reductase (QFR) from Wolinella succinogenes, a target closely related to QFRs from the human pathogens Helicobacter pylori and Campylobacter jejuni. For a better understanding of the hitherto structurally unexplored substrate binding pocket, a structure activity relationship (SAR) study was carried out. Analogues of lawsone (2-hydroxy-1,4-naphthoquinone 3a) were synthesized that vary in length and size of the alkyl side chains (3b-k). A combined study on the prototropic tautomerism of 2-hydroxy-1,4-naphthoquinones series indicated that the 1,4-tautomer is the more stable and biologically relevant isomer and that the presence of the hydroxyl group is crucial for inhibition. Furthermore, 2-bromine-1,4-naphthoquinone (4a-c) and 2-methoxy-1,4-naphthoquinone (5a-b) series were also discovered as novel and potent inhibitors. Compounds 4a and 4b showed IC50 values in low micromolar range in the primary assay and no activity in the counter DT-diaphorase assay.
• Fieser et al., Journal of the American Chemical Society, 1948, vol. 70, p. 3177
  作者：Fieser et al.

  DOI：——

  日期：——
• Parts‐per‐Million‐Level, Catalytic [3+2]‐Annulations for the Asymmetric Synthesis of Methanobenzo[7]annulenes
  作者：Guguloth Thirupathi、Etikala Ashok、A. Suresh Kumar、Dhevalapally B. Ramachary

  DOI：10.1002/chem.202103254

  日期：2021.12.23

  Methanobenzo[7]annulenes. Parts-per-million catalyst loading for [3+2]-annulations. An unprecedented, ppm-level, catalytic asymmetric [3+2]-annulation of 3-alkyl-lawsones with nitroethylenes is reported. It is an efficient, sustainable, catalytic asymmetric annulation reaction for the synthesis of chiral methanobenzo[7]annulenes, which are part of many antibiotics.

  甲烷苯并[7]环烯。[3+2]-环化的百万分之一催化剂负载。报道了一种前所未有的 ppm 级催化不对称 [3+2]-环化 3-烷基-劳森酮与硝基乙烯。它是一种有效、可持续、催化不对称环化反应，用于合成手性甲烷苯并 [7] 环烯，这是许多抗生素的一部分。