3-<(tert-butyldimethylsilyl)oxy>-4,5-dimethoxybenzaldehyde | 122271-47-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-<(tert-butyldimethylsilyl)oxy>-4,5-dimethoxybenzaldehyde
• 英文别名: 3-[(tert-butyldimethylsilyl)oxy]-4,5-dimethoxybenzaldehyde；3-{[tert-Butyl(dimethyl)silyl]oxy}-4,5-dimethoxybenzaldehyde；3-[tert-butyl(dimethyl)silyl]oxy-4,5-dimethoxybenzaldehyde
• CAS: 122271-47-0
• 化学式: C₁₅H₂₄O₄Si
• 分子量: 296.439
• InChiKey: QIBRUGROXKKVGI-UHFFFAOYSA-N

物化性质

• 熔点：
  135 °C
• 沸点：
  356.9±42.0 °C(Predicted)
• 密度：
  1.017±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-<(tert-butyldimethylsilyl)oxy>-4,5-dimethoxybenzaldehyde 在 sodium tetrahydroborate 、 乙酰氯 、 calcium chloride 、 lithium hexamethyldisilazane 、 原甲酸三甲酯 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 21.75h， 生成 (+)-5'-hydroxymethylpiperitol
  参考文献：
  名称：

  Stereocontrolled Total Syntheses of Optically Active Furofuran Lignans

  摘要：

  Plant products (+)-sesamin, (+)-sesaminol, (+)-methylpiperitol, (+)-aschantin, and (+)-5'-hydroxymethylpiperitol were synthesized in a highly stereocontrolled manner through L-proline-catalyzed bifunctional-urea-accelerated cross-aldol reaction, followed by biomimetic construction of the furofuran lignan skeleton through a quinomethide intermediate.

  DOI：

  10.1055/s-0034-1378812
• 作为产物：
  描述：

  3-<(tert-butyldimethylsilyl)oxy>-4,5-dimethoxybenzyl alcohol 在 sodium acetate 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以95%的产率得到3-<(tert-butyldimethylsilyl)oxy>-4,5-dimethoxybenzaldehyde
  参考文献：
  名称：

  Antineoplastic agents. 166. Isolation, structure, and synthesis of combretastatin C-1

  摘要：

  DOI：

  10.1021/jo00278a023

文献信息

• E-Combretastatin and E-resveratrol structural modifications: Antimicrobial and cancer cell growth inhibitory β-E-nitrostyrenes
  作者：Robin K. Pettit、George R. Pettit、Ernest Hamel、Fiona Hogan、Bryan R. Moser、Sonja Wolf、Sandy Pon、Jean-Charles Chapuis、Jean M. Schmidt

  DOI：10.1016/j.bmc.2009.07.076

  日期：2009.9

  As part of a broad-based SAR investigation of E-resveratrol (strong sirtuin activator and antineoplastic) and the anticancer vascular-targeting combretastatin-type stilbenes, a series of twenty-three beta-E-nitrostyrenes was synthesized in order to evaluate potential antineoplastic, antitubulin, and antimicrobial activities. The beta-E-nitrostyrenes evaluated ranged from monosubstituted phenols to trimethoxy and 3-methoxy- 4,5-methylenedioxy derivatives. Two of the beta-nitrostyrenes were synthesized as water-soluble sodium phosphate derivatives (4t, 4v). All except four (4r, 4s, 4t, 4u) of the series significantly inhibited a minipanel of human cancer cell lines. All but eight led to an IC50 of < 10 mu M for inhibition of tubulin polymerization, and all except three (4l, 4t, 4v) displayed antimicrobial activity. (C) 2009 Published by Elsevier Ltd.
• Antineoplastic Agents. 509. Synthesis of Fluorcombstatin Phosphate and Related 3-Halostilbenes^,1
  作者：George R. Pettit、Mathew D. Minardi、Heidi J. Rosenberg、Ernest Hamel、Michael C. Bibby、Sandie W. Martin、M. Katherine Jung、Robin K. Pettit、Timothy J. Cuthbertson、Jean-Charles Chapuis

  DOI：10.1021/np058038i

  日期：2005.10.1

  The present SAR study of combretastatin A-3 (3a) focused on replacement of the 3-hydroxyl group by a series of halogens. That approach with Z-stilbenes resulted in greatly enhanced (> 10-100-fold) cancer cell growth inhibition against a panel of human cancer cell lines and the murine P388 lymphocytic leukemia cell line. Synthesis of the 3-fluoro-Z-stilbene designated fluorcombstatin (11a) and its potassium 3'-O-phosphate derivative (16c) by the route 7 -> 8a -> 11a -> 14 -> 16c illustrates the general synthetic pathway. The 3'-O-phosphoric acid ester (15) of 3-bromo-Z-stilbene 13a was also converted to representative cation salts to evaluate the potential for improved aqueous solubility, and the potassium salt (16 mg/mL in water) proved most useful. The fluoro (11a), chloro (12a), and bromo (13a) halocombstatins were nearly equivalent to combretastatin A-4 (1a) as inhibitors of tubulin polymerization and of the binding of colchicine to tubulin. The tubulin binding in cell-free systems was also retained in human umbilical vein endothelial cells. All three halocombstatins retained the powerful human cancer cell line inhibitory activity of combretastatin A-4 (la) and proved superior to combretastatin A-3 (3a). In addition, the halocombstatins targeted Gram-positive bacteria and Cryptococcus neoformans.
• Anticancer effects of the metabolic products of the resveratrol analogue, DMU-212: Structural requirements for potency
  作者：Vasilis P. Androutsopoulos、Ketan C. Ruparelia、Athanasios Papakyriakou、Harilaos Filippakis、Aristeidis M. Tsatsakis、Demetrios A. Spandidos

  DOI：10.1016/j.ejmech.2011.03.049

  日期：2011.6

  The methoxylated trans-stilbene resveratrol analogue, (E)-3,4,5,4'-tetramethoxystilbene (1), has shown promising antiproliferative activity in in vitro cell line and in vivo models. In vivo I gives rise to several metabolic products through demethylation or hydroxylation reactions at the stilbene moiety. In the present study we examined the anticancer activity of 1 and the metabolites (E)-3'-hydroxy-3,4,5,4'-tetramethoxystilbene (2), (E)-4'-hydroxy-3,4,5-trimethoxystilbene (3), (E)-4-hydroxy-3,5,4'-trimethoxystilbene (4) and (E)-3-hydroxy-4,5,4'-trimethoxystilbene (5) by means of cell viability testing, cell cycle analysis, immunostaining and Western blotting. Compounds 1 and 2 exhibited submicromolar toxicity in MCF-7 breast adenocarcinoma and HepG2 hepatoma cells, whereas 3, 4 and 5 were inactive in terms of inhibition of cellular proliferation. Incubation with 1 or 2 at 10 mu M for 24 h induced apoptosis and G2/M cell cycle arrest in MCF-7 and HepG2 cells. Immunostaining of MCF-7 cells for beta-tubulin in the presence of either 1 or 2 revealed shorter localization of the protein around the nucleus, as compared to control cells. Western blot analyses further demonstrated that treatment with either 1 or 2 at concentrations between 30 and 50 mu M for 24 h caused a downregulation in the levels of beta-tubulin and cyclin D1 expression and an upregulation in the levels of p53 expression in MCF-7 and HepG2 cells. 2 further increased the ratio of mRNA levels of the apoptosis-related genes Bax/Bcl-xL in both MCF-7 and HepG2 cells in a dose-dependent manner. We conclude that 2 inhibits HepG2 and MCF-7 cellular proliferation by inducing apoptosis and G2/M arrest through p53 and Bax/Bcl-xL upregulation. Our findings further demonstrate that trimethoxy substitutions along with the presence of a methoxy group at position 4' are necessary for retaining the activity of 1. (C) 2011 Elsevier Masson SAS. All rights reserved.
• SINGH, SHEO BUX;PETTIT, GEORGE R., J. ORG. CHEM., 54,(1989) N7, C. 4105-4114
  作者：SINGH, SHEO BUX、PETTIT, GEORGE R.

  DOI：——

  日期：——
• Stereocontrolled Total Syntheses of Optically Active Furofuran Lignans
  作者：Yoshitaka Hamashima、Toshiyuki Kan、Makoto Inai、Ryo Ishikawa、Naoto Yoshida、Nana Shirakawa、Yusuke Akao、Yusuke Kawabe、Tomohiro Asakawa、Masahiro Egi

  DOI：10.1055/s-0034-1378812

  日期：——

  Plant products (+)-sesamin, (+)-sesaminol, (+)-methylpiperitol, (+)-aschantin, and (+)-5'-hydroxymethylpiperitol were synthesized in a highly stereocontrolled manner through L-proline-catalyzed bifunctional-urea-accelerated cross-aldol reaction, followed by biomimetic construction of the furofuran lignan skeleton through a quinomethide intermediate.