(S)-4-phenyl-1,2-dihydronaphthalen-1-ol | 1313594-44-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-4-phenyl-1,2-dihydronaphthalen-1-ol
• 英文别名: (1S)-4-phenyl-1,2-dihydronaphthalen-1-ol
• CAS: 1313594-44-3
• 化学式: C₁₆H₁₄O
• 分子量: 222.287
• InChiKey: UMXYBQZDGSWQST-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (S)-4-phenyl-1,2-dihydronaphthalen-1-ol 在 间氯过氧苯甲酸 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 (1aR,3S,7bS)-7b-phenyl-1a,2,3,7b-tetrahydronaphtho[1,2-b]oxiren-3-ol
  参考文献：
  名称：

  A catalytic asymmetric entry to enantioenriched tertiary naphthoquinols via a facile tandem oxidation/ring-opening sequence

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2011.04.020
• 作为产物：
  描述：

  (S)-1,2-dihydro-1-hydroxy-7-methoxynaphthalene 在 咪唑 、 4-二甲氨基吡啶 、 四(三苯基膦)钯 、 四丁基氟化铵 、 溴 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 77.0h， 生成 (S)-4-phenyl-1,2-dihydronaphthalen-1-ol
  参考文献：
  名称：

  A catalytic asymmetric entry to enantioenriched tertiary naphthoquinols via a facile tandem oxidation/ring-opening sequence

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2011.04.020

文献信息

• 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.