1,7-bis(4'-hydroxyphenyl)-3-heptanone | 130233-83-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 1,7-bis(4'-hydroxyphenyl)-3-heptanone
• 英文别名: 1,7-bis(4-hydroxyphenyl)-heptan-3-one；1,7-bis(4-hydroxyphenyl)-3-heptanone；1,7-bis(4-hydroxyphenyl)heptan-3-one；3-Platyphyllone；acerogenin 3；acerogenin G
• CAS: 130233-83-9
• 化学式: C₁₉H₂₂O₃
• 分子量: 298.382
• InChiKey: QUHYUSAHBDACNG-UHFFFAOYSA-N

物化性质

• 沸点：
  526.7±40.0 °C(Predicted)
• 密度：
  1.149±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  1,7-bis(4'-hydroxyphenyl)-3-heptanone 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以90%的产率得到centrolobol
  参考文献：
  名称：

  Synthesis of Natural and Non-natural Curcuminoids and Their Neuroprotective Activity against Glutamate-Induced Oxidative Stress in HT-22 Cells

  摘要：

  A strategy for the synthesis of natural and non-natural 5-deoxy-6,7-dihydrocurcuminoids (diarylheptanoids) was developed for the preparation of 14 compounds with varying aromatic substituent patterns and a different functionality in the aliphatic seven-carbon chain. The in vitro protective activity against glutamate-induced neuronal cell death was examined in the murine hippocampal cell line HT-22 to find structural motifs responsible for neuroprotective effects in vitro. Among the tested compounds the ferulic acid-like unit, present in the structures of (E)-1,7-bis(4-hydroxy-3-methoxyphenyl)hept-1-en-3-one (5) and (E)-1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)hept-1-en-3-one (7), appeared to be an important feature for protection against glutamate-induced neurotoxicity. Both compounds demonstrated significant neuroprotective activity in a concentration range between 1 and 25 μM without showing toxic effects in a cytotoxicity assay with HT-22 cells. Furthermore, (E)-1,7-bis(3,4-dihydroxyphenyl)hept-1-en-3-one (9), exhibiting a caffeic acid-like structural motif, displayed a neuroprotective activity at a nontoxic concentration of 25 μM. In contrast, (1E,6E)-1,7-bis(3,4-dihydroxyphenyl)hepta-1,6-diene-3,5-dione (4, di-O-demethylcurcumin) showed mainly cytotoxic effects. A corresponding single-ring analogue that contains the ferulic acid-like unit as an enone was not active.

  DOI：

  10.1021/np500396y
• 作为产物：
  描述：

  Centrolobol; (R)-(-)-1,7-双对羟基苯基-3-庚醇 在 aluminum isopropoxide 作用下， 以 环己酮 、 甲苯 为溶剂， 生成 1,7-bis(4'-hydroxyphenyl)-3-heptanone
  参考文献：
  名称：

  Studies on the constituents of aceraceae plants. VII. Diarylheptanoids from Acer griseum and Acer triflorum.

  摘要：

  一种名为aceroside IX (1) 的二苯庚烷类糖苷，化学式为C30H40O12, [α]D -63.5°，从灰背枫 (Acer griseum) 和三花枫 (A. triflorum) 的树皮中分离得到。另一种名为aceroside X (2) 的二苯庚烷类糖苷，化学式为C25H31O8，熔点121°， [α]21D -29.7°，以及表儿茶素，从灰背枫的树皮中分离得到，并通过薄层色谱在三花枫中检测到。在酸水解后，1生成了一种新的二苯庚烷类化合物acerogenin G (3)，化学式为C19H22O3，经过鉴定为(-)-centrolobol (5) 的酮衍生物，并产生葡萄糖和阿比糖。在部分水解过程中，1得到aceroside X (2) 和阿比糖。通过对3及其单甲基醚 (6) 的质谱分析结果，发现aceroside IX 的糖基通过与acerogenin G (3) 的C-4"位点的酚羟基结合。后者通过对1进行甲基化后酸水解生成。根据碳-13核磁共振谱分析，并与aceroside VIII (7) 的谱图比较，确定acerosides (1) 和X (2) 分别为acerogenin G 的4"-O-β-D-apiofuranosyl-(1→6)-β-D-glucopyranoside 和4"-O-β-D-glucopyranoside。

  DOI：

  10.1248/cpb.38.1506

文献信息

• Bio-inspired oxidative phenolic coupling: Total synthesis of the diarylether heptanoid (±)-pterocarine
  作者：M. Quamar Salih、Christopher M. Beaudry

  DOI：10.1016/j.tetlet.2017.04.015

  日期：2017.5

  pterocarine, is expeditiously synthesized using a bioinspired intramolecular oxidative phenolic coupling of acerogenin G. The cyclization precursor is prepared from a simple cinnamic acid derivative in three high yielding synthetic operations. The key oxidative coupling is inspired by biosynthetic hypotheses; however, the oxidative coupling proceeds with concomitant hydroxylation of the diphenyl ether motif

  二芳基醚庚烷类天然产物蝶呤碱是利用生物素启发的铜绿皂苷元G分子快速合成的。环化前体是由一种简单的肉桂酸衍生物以三种高产率的合成操作制得的。关键的氧化偶合是受生物合成假设启发的。然而，氧化偶合伴随着二苯醚基序的羟基化而进行。
• Six cytotoxic annonaceous acetogenins from Annona squamosa seeds
  作者：Yong Chen、Jian-wei Chen、Yu Wang、Sha-sha Xu、Xiang Li

  DOI：10.1016/j.foodchem.2012.05.041

  日期：2012.12

  of custard apple seeds led to the isolation of six new annonaceous acetogenins: annosquacins A–D (1–4), annosquatin A (5) and annosquatin B (6). Their structures were elucidated by spectroscopic analysis. Compounds 1–4 are adjacent bistetrahydrofuran annonaceous acetogenins. Compounds 5 and 6 are non-adjacent bistetrahydrofuran annonaceous acetogenins and the first examples in which the tetrahydrofuran

  南美番荔枝（Annona squamosa L.）是一种可食用的热带水果，其种子已在中国南方用作治疗“恶性疮”（癌）的民间药和杀虫剂。导致的六个新的番荔枝内酯隔离释迦种子的乙醇级分的植物化学物质调查：annosquacins A-d（1 - 4），annosquatin A（5）和annosquatin B（6）。通过光谱分析阐明了它们的结构。化合物1 - 4相邻bistetrahydrofuran番荔枝内酯。化合物5和6是不相邻的双四氢呋喃非乙酰乙酸原蛋白，并且是第一个例子，其中四氢呋喃环系统位于C-9和C-20之间。的绝对构型1 - 6是由莫舍方法的应用程序定义。化合物1 - 6表现出强效的细胞毒活性在体外对5个人肿瘤细胞系。化合物5和6分别显示出对MCF-7和A-549细胞系的高选择性。
• Total synthesis of acerogenins E, G and K, and centrolobol
  作者：Tetsuhiro Ogura、Toyonobu Usuki

  DOI：10.1016/j.tet.2013.01.065

  日期：2013.4

  The first total synthesis of the diaiylheptanoid acerogenins E and K, isolated from Acer nikoense MAXIM., is described. Formation of the 13-membered m,m-cyclophane skeleton was successfully achieved on the basis of a domino process involving a Miyaura arylborylation intramolecular Suzuki reaction. The cyclization precursor was prepared via a Wittig reaction and Claisen Schmidt condensation, which proceeded in moderate yields. The total synthesis of acerogenin G and centrolobol was also achieved from a common synthetic intermediate. (C) 2013 Elsevier Ltd. All rights reserved.
• Platyphylloside: Metabolism and digestibility reductionin vitro
  作者：Kerstin Sunnerheim-Sjöberg、Per-Göran Knutsson

  DOI：10.1007/bf02027566

  日期：1995.9

  The metabolism of platyphylloside [(5S)-5-hydroxy-1,7-bis-(4-hydroxyphenyl)-3-heptanone-5-O-beta-D-glucopyranoside]-known to reduce digestibility-was studied in vitro in sheep rumen liquor. Platyphylloside is hydrolyzed to 5-hydroxy-3-platyphyllone [(5S)-5-hydroxy-1,7-bis-(4-hydroxyphenyl)-3-heptanone], which is reduced to centrolobol [1,7-bis-(4-hydroxyphenyl)-3-heptanol], via 3-platyphyllone [7-bis-(4-hydroxyphenyl)-3-heptanone]. The digestibility-reducing effect was shown to be correlated with the concentration of centrolobol.
• Identification of Centrolobol as the Platyphylloside Metabolite Responsible for the Observed Effect on in Vitro Digestibility of Hay
  作者：Kerstin Sunnerheim、Katharina Bratt

  DOI：10.1021/jf040135e

  日期：2004.9.1

  Syntheses of the metabolites from platyphylloside, a phenol causing digestibility inhibition in rumen fluid, have been performed to identify the active metabolite. 1,7-Bis(4'-hydroxyphenyl)-3-heptanone (3-platyphyllone), racemic, and the two enantiomers of 1,7-bis(4'-hydroxyphenyl)-3-heptanol (centrolobol) and 1,7-bis(4-hydroxyphenyl)heptane (platyphyllane) were synthesized and tested regarding digestibility inhibition in vitro in cow rumen fluid. All compounds tested induced a decreased digestion. Centrolobol was found to be the metabolite causing the observed effect, and (R)-centrolobol was found to be the enantiomer formed in the rumen liquor in vitro.