(S)-4-hydroxy-4-phenylnaphthalen-1(4H)-one | 1313594-45-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-4-hydroxy-4-phenylnaphthalen-1(4H)-one
• 英文别名: (4S)-4-hydroxy-4-phenylnaphthalen-1-one
• CAS: 1313594-45-4
• 化学式: C₁₆H₁₂O₂
• 分子量: 236.27
• InChiKey: AILCRESYMVLLMM-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (S)-1,2-dihydro-1-hydroxy-7-methoxynaphthalene 在 咪唑 、 光气 、 双(乙腈)氯化钯(II) 、 三苯胂 、 四丁基氟化铵 、 溴 、 三乙胺 、 N,N-二异丙基乙胺 、 间氯过氧苯甲酸 作用下， 以 二甲基亚砜 为溶剂， 生成 (S)-4-hydroxy-4-phenylnaphthalen-1(4H)-one
  参考文献：
  名称：

  Synthesis and evaluation of (1S)-1,2-dihydro-1-naphthalenol derivatives against PANC-1 cells

  摘要：

  Several derivatives of (1S)-1,2-dihydro-1-naphthalenol ((S)-7) have been synthesized and evaluated against human pancreatic adenocarcinoma cell line PANC-1 under nutrient-rich and nutrient-deprived conditions. The tert-butyldiphenylsilyl protected homoallylic alcohol (S)-8 displayed cytotoxicity against PANC-1 cells with an LC50 value of 11 mu M in the absence of essential amino acids, glucose, and serum, while exhibiting no cytotoxicity under nutrient-rich conditions. The observed selective antitumor activity of (S)-8 under nutrient deprived conditions suggests its potential as a promising lead structure for the design of future anti-pancreatic cancer agents. (C) 2015 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2015.02.050

文献信息

• A catalytic asymmetric entry to enantioenriched tertiary naphthoquinols via a facile tandem oxidation/ring-opening sequence
  作者：Alice Kwan、Johanna Stein、Dora Carrico-Moniz

  DOI：10.1016/j.tetlet.2011.04.020

  日期：2011.7

  The tertiary naphthoquinol is a key structural component of the antitumor natural products spiroxins A-E. Herein we report the first catalytic asymmetric approach to the tertiary naphthoquinol C4' stereogenic center present in the spiroxin framework, via tandem oxidation/ring-opening of a cyclic 3,4-epoxyalcohol. This new route allows a facile entry into relatively inaccessible tertiary naphthoquinols with high enantioselectivity and without the need of chiral auxiliaries. (C) 2011 Elsevier Ltd. All rights reserved.
• Synthesis and evaluation of (1S)-1,2-dihydro-1-naphthalenol derivatives against PANC-1 cells
  作者：Hong Zhang、Kellen Kartub、Alice Kwan、Andrew Webb、Dora Carrico-Moniz

  DOI：10.1016/j.tetlet.2015.02.050

  日期：2015.3

  Several derivatives of (1S)-1,2-dihydro-1-naphthalenol ((S)-7) have been synthesized and evaluated against human pancreatic adenocarcinoma cell line PANC-1 under nutrient-rich and nutrient-deprived conditions. The tert-butyldiphenylsilyl protected homoallylic alcohol (S)-8 displayed cytotoxicity against PANC-1 cells with an LC50 value of 11 mu M in the absence of essential amino acids, glucose, and serum, while exhibiting no cytotoxicity under nutrient-rich conditions. The observed selective antitumor activity of (S)-8 under nutrient deprived conditions suggests its potential as a promising lead structure for the design of future anti-pancreatic cancer agents. (C) 2015 Published by Elsevier Ltd.