4-(Cyclohexylmethyl)-2,5-dihydroxy-benzaldehyde | 1366474-00-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(Cyclohexylmethyl)-2,5-dihydroxy-benzaldehyde
• 英文别名: 4-(cyclohexylmethyl)-2,5-dihydroxybenzaldehyde
• CAS: 1366474-00-1
• 化学式: C₁₄H₁₈O₃
• 分子量: 234.295
• InChiKey: YYZQZRGDXWBYBE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1,4-dibromo-2,5-bis(methoxymethoxy)benzene 在 三乙基硅烷 、 正丁基锂 、 三氟乙酸 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 9.99h， 生成 4-(Cyclohexylmethyl)-2,5-dihydroxy-benzaldehyde
  参考文献：
  名称：

  Evaluation of HIV-1 inhibition by stereoisomers and analogues of the sesquiterpenoid hydroquinone peyssonol A

  摘要：

  Peyssonol A, a brominated natural product with documented anti-HIV-1 activity, was synthesized racemically along with 6 isomers and 15 truncated analogues and synthetic precursors. These compounds were screened in a cell-based assay against a recombinant HIV-1 strain to investigate structure-activity relationships. The results obtained suggest that both the aliphatic and aromatic domains of peyssonol A are responsible for its potency, while the stereochemical configuration of the substituents on the aliphatic domain, including their bromine atom, are largely irrelevant. Although none of the analogues tested were as potent as the parent natural product, several exhibited greater therapeutic indices due to reduced cytotoxicity, noting that nearly all compounds tested were measurably cytotoxic. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.01.098

文献信息

• UNIQUE HALOGEN-INDUCED CYCLIZATIONS, REAGENTS THEREFOR, AND COMPOUNDS PRODUCED THEREBY
  申请人：Snyder Scott Alan

  公开号：US20140243404A1

  公开（公告）日：2014-08-28

  This disclosure is related to halonium compounds useful for cyclization of polyenes, alkenoic acids, and alkenyl alkyl ethers, and halogenation of aromatic compounds. The synthesis of such halonium compounds, compounds made using such halonium compounds, and synthesis of natural compounds, including decalins, using the halonium compounds is also disclosed. A representative halonium compound of the disclosure is:

  本披露涉及有用于多烯环化、烯酸和烯基烷醚环化以及芳香族化合物卤代的卤化物化合物。披露了这种卤化物化合物的合成、使用这种卤化物化合物制备的化合物以及使用卤化物化合物合成天然化合物，包括蒎烯。本披露的代表性卤化物化合物为：
• Evaluation of HIV-1 inhibition by stereoisomers and analogues of the sesquiterpenoid hydroquinone peyssonol A
  作者：Daniel S. Treitler、Zhufang Li、Mark Krystal、Nicholas A. Meanwell、Scott A. Snyder

  DOI：10.1016/j.bmcl.2013.01.098

  日期：2013.4

  Peyssonol A, a brominated natural product with documented anti-HIV-1 activity, was synthesized racemically along with 6 isomers and 15 truncated analogues and synthetic precursors. These compounds were screened in a cell-based assay against a recombinant HIV-1 strain to investigate structure-activity relationships. The results obtained suggest that both the aliphatic and aromatic domains of peyssonol A are responsible for its potency, while the stereochemical configuration of the substituents on the aliphatic domain, including their bromine atom, are largely irrelevant. Although none of the analogues tested were as potent as the parent natural product, several exhibited greater therapeutic indices due to reduced cytotoxicity, noting that nearly all compounds tested were measurably cytotoxic. (C) 2013 Elsevier Ltd. All rights reserved.