1-(4-(benzyloxy)phenyl)hex-5-en-3-ol | 850251-73-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-(4-(benzyloxy)phenyl)hex-5-en-3-ol
• 英文别名: 1-(4-Phenylmethoxyphenyl)hex-5-en-3-ol
• CAS: 850251-73-9
• 化学式: C₁₉H₂₂O₂
• 分子量: 282.382
• InChiKey: HVDPXLLDCXTEJN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 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：

  1-(4-(benzyloxy)phenyl)hex-5-en-3-ol 在 Pseudomonas cepacia lipase 、 potassium carbonate 作用下， 以 甲醇 、 异丙醚 为溶剂， 反应 25.0h， 生成 (S)-1-(4-(benzyloxy)phenyl)hex-5-en-3-ol
  参考文献：
  名称：

  Lipase-Catalyzed Resolution of 1-[4-(Benzyloxy)phenyl]hex-5-en-3-ol: Synthesis of (-)-Centrolobine

  摘要：

  已开发出一种实用且高效的制备同烯丙醇的方法，并成功进行了酶促分解。这一脂肪酶催化的分解过程已针对不同脂肪酶和溶剂进行了优化。此外，还应用了Mitsunobu策略以回收不需要的异构体。进一步强化光学纯度的同烯丙醇已用于合成（-）-中心罗宾。

  DOI：

  10.14233/ajchem.2017.20816
• 作为产物：
  描述：

  3-[4-(苄氧基)苯基]-1-丙醇 在 草酰氯 、 二甲基亚砜 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.5h， 生成 1-(4-(benzyloxy)phenyl)hex-5-en-3-ol
  参考文献：
  名称：

  Lipase-Catalyzed Resolution of 1-[4-(Benzyloxy)phenyl]hex-5-en-3-ol: Synthesis of (-)-Centrolobine

  摘要：

  已开发出一种实用且高效的制备同烯丙醇的方法，并成功进行了酶促分解。这一脂肪酶催化的分解过程已针对不同脂肪酶和溶剂进行了优化。此外，还应用了Mitsunobu策略以回收不需要的异构体。进一步强化光学纯度的同烯丙醇已用于合成（-）-中心罗宾。

  DOI：

  10.14233/ajchem.2017.20816

文献信息

• Functionalized alkoxy arene diazonium salts from paracetamol
  作者：Bernd Schmidt、René Berger、Frank Hölter

  DOI：10.1039/b924619c

  日期：——

  as a convenient one-flask transformation with consecutive addition of the appropriate reagents. Exchange of solvents or removal of byproducts prior to isolation of the product is not required. The arene diazonium salts are isolated from the reaction mixture by simple filtration. Two complementary protocols are presented, and the utility of the reaction is exemplified for a synthesis of the diarylheptanoid

  芳族乙酰胺四氟硼酸酯可以由芳族乙酰胺经一系列的脱乙酰基，重氮化和沉淀（由阴离子交换诱导）合成。该反应以方便的一瓶转化进行，并连续添加适当的试剂。不需要在分离产物之前交换溶剂或除去副产物。通过简单的过滤从反应混合物中分离出芳烃重氮盐。提出了两种互补的方案，并举例说明了该反应用于合成二芳基庚烷天然产物去-O-甲基中心洛宾的方法。
• Synthesis of tetrahydropyranyl diarylheptanoids from Dioscorea villosa
  作者：Kawalee Kantee、Vatcharin Rukachaisirikul、Kwanruthai Tadpetch

  DOI：10.1016/j.tetlet.2016.06.102

  日期：2016.8

  Concise syntheses of four tetrahydropyranyl diarylheptanoids isolated from Dioscorea villosa have been described. The key features include Prins cyclization to construct the tetrahydropyran cores, Keck asymmetric allylation, and Mitsunobu inversion. Optimization of the Prins cyclization conditions in order to minimize racemization has been described. Our syntheses also confirmed the absolute stereochemistry

  已经描述了从薯Di薯Di中分离得到的四种四氢吡喃基二芳基庚烷的简捷合成方法。主要特征包括Prins环化以构建四氢吡喃核，Keck不对称烯丙基化和Mitsunobu转化。已经描述了优化Prins环化条件以最小化外消旋化。我们的合成还证实了天然产物的绝对立体化学。
• Synthesis of a novel diarylheptanoid isolated from Zingiber officinale
  作者：Gregory D. Parker、Peter T. Seden、Christine L. Willis

  DOI：10.1016/j.tetlet.2009.03.154

  日期：2009.7

  Syntheses of 4-acetoxy-2,6-disubstituted tetrahydropyrans via Prins cyclisation of homoallylic alcohols with benzylic aldehydes are described and the methodology is applied in the total synthesis of diarylheptanoid 1 confirming both the structure and absolute configuration of the natural product.

  描述了通过均芳醇与苄基醛的Prins环化来合成4-乙酰氧基-2,6-二取代的四氢吡喃，并将该方法应用于二芳基庚烷1的全合成中，从而确认了天然产物的结构和绝对构型。
• Total synthesis of (−)-centrolobine: β-C-glycoside formation via a tandem Grignard addition and stereoselective hemi-ketal reduction
  作者：Michael P. Jennings、Ryan T. Clemens

  DOI：10.1016/j.tetlet.2005.01.156

  日期：2005.3

  It has been demonstrated that an aryl-β-C-glycoside can be efficiently constructed via a sequence consisting of Brown asymmetric allylation, ring-closing metathesis, hydrogenation, nucleophilic addition, and stereoselective Et3SiH reduction. The antibiotic natural product (−)-centrolobine was synthesized in this manner utilizing only five steps with an overall 53% yield.

  已经证明，可以通过由布朗不对称烯丙基化，闭环易位，氢化，亲核加成和立体选择性Et 3 SiH还原组成的序列有效地构建芳基-β - C-糖苷。以这种方式仅使用五个步骤就合成了抗生素天然产物（-）-中心洛宾，总产率为53％。
• New synthesized polyoxygenated diarylheptanoids suppress lipopolysaccharide-induced neuroinflammation
  作者：Anna Santarsiero、Antonella Bochicchio、Maria Funicello、Paolo Lupattelli、Sabine Choppin、Françoise Colobert、Gilles Hanquet、Lucie Schiavo、Paolo Convertini、Lucia Chiummiento、Vittoria Infantino

  DOI：10.1016/j.bbrc.2020.06.122

  日期：2020.9

  In neurodegenerative diseases, such as Alzheimer's disease, Huntington's disease, Parkinson's disease and multiple sclerosis, neuroinflammation induced by the microglial activation plays a crucial role. In effort to develop effective anti-neuroinflammatory compounds, different new linear polyoxygenated diarylheptanoids were synthesized. In LPS-triggered BV-2 microglial cells their ability to reduce the concentration of IL-6 and TNF-alpha pro-inflammatory cytokines was evaluated. Moreover, their effect on NF-kappa B and ATP citrate lyase (ACLY), a recently emerged target of metabolic reprogramming in inflammation, was assessed. Finally, we turned our attention to inflammatory mediators derived from the cleavage of citrate catalyzed by ACLY: prostaglandin E-2, nitric oxide and reactive oxygen species. All compounds showed null or minimal cytotoxicity; most of them had a great anti-neuroinflammatory activity. Diarylheptanoids 6b and 6c, bearing a halide atom and benzyl ether protective groups, exhibited the best effect since they blocked the secretion of all inflammatory mediators analyzed and reduced NF-kB and ACLY protein levels. (c) 2020 Elsevier Inc. All rights reserved.