3-(Benzyloxy)-1-(bis(phenylthio)methyl)benzene | 96995-00-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-(Benzyloxy)-1-(bis(phenylthio)methyl)benzene
• 英文别名: 3-(benzyloxy)-1-[bis(phenylthio)methyl]benzene；3-benzyloxybenzaldehyde bis(phenylthio) acetal；3-benzyloxybenzaldehyde bis(phenylthio)acetal；1-[Bis(phenylsulfanyl)methyl]-3-phenylmethoxybenzene
• CAS: 96995-00-5
• 化学式: C₂₆H₂₂OS₂
• 分子量: 414.592
• InChiKey: IQCYKWORFWKUPW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  59.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(Benzyloxy)-1-(bis(phenylthio)methyl)benzene 在 1,3-二甲基-2-咪唑啉酮 、 lithium aluminium tetrahydride 、 正丁基锂 、 镍 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 8.5h， 生成 肠二醇
  参考文献：
  名称：

  大鼠，猪和人肝微粒体对哺乳动物木脂体肠内酯和肠二醇的氧化代谢。

  摘要：

  根据HPLC / MS和GC / MS分析，用acrolor处理的雄性Wistar大鼠的肝微粒体将肠内酯生物转化为12种代谢物，其中6种在芳族上带有一个额外的羟基，在脂族部分上带有6个羟基。借助于合成的参考化合物，芳族羟基化产物鉴定为肠内酯在任一芳族环的原始酚羟基的对位和两个邻位均被单羟基化。描述了参考化合物的合成及其光谱表征。肠糖被肝微粒体从经aroclor处理的雄性大鼠代谢为三种芳香族和四种脂肪族单羟基化代谢产物。芳族羟基化发生在原始酚羟基的对位和两个邻位。

  DOI：

  10.1021/jf9809176
• 作为产物：
  描述：

  3-苄氧基苯甲醛 、 苯硫酚 在 三氯化铝 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以81%的产率得到3-(Benzyloxy)-1-(bis(phenylthio)methyl)benzene
  参考文献：
  名称：

  Enantioselective Synthesis of Natural Dibenzylbutyrolactone Lignans (-)-Enterolactone, (-)-Hinokinin, (-)-Pluviatolide, (-)-Enterodiol, and Furofuran Lignan (-)-Eudesmin via Tandem Conjugate Addition to .gamma.-Alkoxybutenolides

  摘要：

  A general and efficient method is described for the asymmetric synthesis of a variety of lignans. 5-(Menthyloxy)-2(5H)-furanones 5 proved to be excellent chiral synthons in this respect and could be transformed with complete stereoselectivity into a number of lignans. The addition of lithiated dithianes 7 to enantiomerically pure butenolides 5 was followed by quenching of the resulting lactone enolate anions with a benzylbromide (9) or with an aldehyde (6). This tandem addition quenching procedure gave the diastereomerically pure adducts 11, 26, or 27 in 50-67% yield, with a carbon skeleton as found in most natural lignans. As examples of the wide applicability of this method, the syntheses of the enantiomerically pure natural lignans (-)-hinokinin (23b), (-)-enterolactone (24a), (-)-pluviatolide (24c), and (-)-enterodiol (25) in overall yields of 29-37% from 5a and (-)-eudesmin (30) in 16% overall yield from 5b are described.

  DOI：

  10.1021/jo00099a033

文献信息

• Transformation of Arctiin to Estrogenic and Antiestrogenic Substances by Human Intestinal Bacteria.
  作者：Li-Hua Xie、Eun-Mi Ahn、Teruaki Akao、Atef Abdel-Monem Abdel-Hafez、Norio Nakamura、Masao Hattori

  DOI：10.1248/cpb.51.378

  日期：——

  After anaerobic incubation of arctiin (1) from the seeds of Arctium lappa with a human fecal suspension, six metabolites were formed, and their structures were identified as (−)-arctigenin (2), (2R,3R)-2-(3′,4′-dihydroxybenzyl)-3-(3″,4″-dimethoxybenzyl)butyrolactone (3), (2R,3R)-2-(3′-hydroxybenzyl)-3-(3″,4″-dimethoxybenzyl)butyrolactone (4), (2R,3R)-2-(3′-hydroxybenzyl)-3-(3″-hydroxy-4″-methoxybenzyl)butyrolactone (5), (2R,3R)-2-(3′-hydroxybenzyl)-3-(3″,4″-dihydroxybenzyl)butyrolactone (6), and (−)-enterolactone (7) by various spectroscopic means including two dimensional (2D)-NMR, mass spectrometry, and circular dichroism. A possible metabolic pathway was proposed on the basis of their structures and the time course of the transformation. Enterolactones obtained from the biotransformation of arctiin and secoisolariciresinol diglucoside (SDG, from the seeds of Linum usitatissium) by human intestinal bacteria were proved to be enantiomers, with the (−)-(2R,3R) and (+)-(2S,3S) configurations, respectively. Compound 6 showed the most potent proliferative effect on the growth of MCF-7 human breast cancer cells in culture among 1 and six metabolites, while it showed inhibitory activity on estradiol-mediated proliferation of MCF-7 cells at a concentration of 10 μM. These results indicate that the transformation of 1 by intestinal flora might be essential for the manifestation of the estrogenic and antiestrogenic activity of 1.

  将从蒡子中提取的 arctiin（1）与人类粪便悬浮液进行厌氧培养后，产生了六种代谢物、它们的结构被鉴定为(-)-旱芹甙元（2）、(2R,3R)-2-(3′,4′-二羟基苄基)-3-(3″,4″-二甲氧基苄基)丁内酯（3）、(2R,3R)-2-(3′-羟基苄基)-3-(3″、4″-二甲氧基苄基）丁内酯 (4)，(2R,3R)-2-（3′-羟基苄基）-3-（3″-羟基-4″-甲氧基苄基）丁内酯 (5)，(2R,3R)-2-（3′-羟基苄基）-3-（3″、4″-二羟基苄基）丁内酯 (6) 和 (-)- 肠内酯 (7)。根据它们的结构和转化的时间过程，提出了一种可能的代谢途径。经人体肠道细菌对 arctiin 和 secoisolariciresinol diglucoside（SDG，来自 Linum usitatissium 的种子）进行生物转化后得到的肠内酯被证明是对映体，分别具有 (-)-(2R,3R) 和 (+)-(2S,3S) 构型。在 1 和 6 个代谢物中，化合物 6 对 MCF-7 人乳腺癌细胞的增殖作用最强，而在 10 μ<小>M浓度下，它对雌二醇介导的 MCF-7 细胞增殖具有抑制活性。这些结果表明，肠道菌群对 1 的转化可能是 1 显示雌激素和抗雌激素活性的关键。
• Development of a Novel Hapten for Radioimmunoassay of the Lignan, Enterolactone in Plasma (Serum). Total Synthesis of (±)-trans-5-Carboxymethoxyenterolactone and Several Analogues
  作者：Taru Mäkelä、Jorma Matikainen、Kristiina Wähälä、Tapio Hase

  DOI：10.1016/s0040-4020(00)00078-8

  日期：2000.3

  A recently developed method for the analysis of the mammalian lignan, enterolactone 1, is based on time-resolved fluoroimmunoassay (TR-FIA) using an europium chelate as a label. This RIA utilizes enterolactone derivatives carrying a carboxylic acid appendage for the production of antiserum and tracer. The synthesis of 5-carboxymethoxyenterolactone 6 and analogues 5, 7 and 8 is described, and their suitability for the method are discussed. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Kirk, N. David; McLaughlin, Leo M.; Lawson, Alexander M., Journal of the Chemical Society. Perkin transactions I, 1985, p. 35 - 38
  作者：Kirk, N. David、McLaughlin, Leo M.、Lawson, Alexander M.、Setchell, Kenneth D.R.、Patel, Shailesh K.

  DOI：——

  日期：——
• Oxidative Metabolism of the Mammalian Lignans Enterolactone and Enterodiol by Rat, Pig, and Human Liver Microsomes
  作者：Eric Jacobs、Manfred Metzler

  DOI：10.1021/jf9809176

  日期：1999.3.1

  microsomes from aroclor-treated male Wistar rats biotransform enterolactone to 12 metabolites, six of which carry an additional hydroxy group at the aromatic and six at the aliphatic moiety according to HPLC/MS and GC/MS analysis. The aromatic hydroxylation products were identified with the help of synthesized reference compounds as enterolactone monohydroxylated in the para position and in both ortho positions

  根据HPLC / MS和GC / MS分析，用acrolor处理的雄性Wistar大鼠的肝微粒体将肠内酯生物转化为12种代谢物，其中6种在芳族上带有一个额外的羟基，在脂族部分上带有6个羟基。借助于合成的参考化合物，芳族羟基化产物鉴定为肠内酯在任一芳族环的原始酚羟基的对位和两个邻位均被单羟基化。描述了参考化合物的合成及其光谱表征。肠糖被肝微粒体从经aroclor处理的雄性大鼠代谢为三种芳香族和四种脂肪族单羟基化代谢产物。芳族羟基化发生在原始酚羟基的对位和两个邻位。
• Enantioselective Synthesis of Natural Dibenzylbutyrolactone Lignans (-)-Enterolactone, (-)-Hinokinin, (-)-Pluviatolide, (-)-Enterodiol, and Furofuran Lignan (-)-Eudesmin via Tandem Conjugate Addition to .gamma.-Alkoxybutenolides
  作者：Arjan van Oeveren、Johan F. G. A. Jansen、Ben L. Feringa

  DOI：10.1021/jo00099a033

  日期：1994.10

  A general and efficient method is described for the asymmetric synthesis of a variety of lignans. 5-(Menthyloxy)-2(5H)-furanones 5 proved to be excellent chiral synthons in this respect and could be transformed with complete stereoselectivity into a number of lignans. The addition of lithiated dithianes 7 to enantiomerically pure butenolides 5 was followed by quenching of the resulting lactone enolate anions with a benzylbromide (9) or with an aldehyde (6). This tandem addition quenching procedure gave the diastereomerically pure adducts 11, 26, or 27 in 50-67% yield, with a carbon skeleton as found in most natural lignans. As examples of the wide applicability of this method, the syntheses of the enantiomerically pure natural lignans (-)-hinokinin (23b), (-)-enterolactone (24a), (-)-pluviatolide (24c), and (-)-enterodiol (25) in overall yields of 29-37% from 5a and (-)-eudesmin (30) in 16% overall yield from 5b are described.