3-<(tert-butyldimethylsilyl)oxy>-4-methoxybenzyl bromide | 97315-20-3

• 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-methoxybenzyl bromide
• 英文别名: 3-(tert-butyldimethylsiloxy)-4-methoxybenzyl bromide；[5-(Bromomethyl)-2-methoxyphenoxy]-tert-butyl-dimethylsilane
• CAS: 97315-20-3
• 化学式: C₁₄H₂₃BrO₂Si
• 分子量: 331.325
• InChiKey: JIXMTRBZMUEJKN-UHFFFAOYSA-N

物化性质

• 沸点：
  335.4±37.0 °C(Predicted)
• 密度：
  1.161±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.97
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-<(tert-butyldimethylsilyl)oxy>-4-methoxybenzyl bromide 在 正丁基锂 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成 (Z)-3,4,5,4',-四甲氧基-3'-羟基二苯乙烯
  参考文献：
  名称：

  Amidobenzothiazoles And Process For The Preparation Thereof

  摘要：

  本发明提供了一种通式A的化合物，可作为潜在的抗人类癌细胞系的抗癌剂，并提供了其制备方法。其中R、R1、R2═H、烷基、烷氧基、卤素、卤代烷基、卤代甲氧基、硝基，G=其中R、R1、R2═H、烷基、烷氧基、卤素、卤代烷基、卤代甲氧基、硝基。

  公开号：

  US20130317231A1
• 作为产物：
  描述：

  3-<(tert-butyldimethylsilyl)oxy>-4-methoxybenzyl alkohol 在 三甲基氯硅烷 、 lithium bromide 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 以73 %的产率得到3-<(tert-butyldimethylsilyl)oxy>-4-methoxybenzyl bromide
  参考文献：
  名称：

  合成甲氧基化白藜芦醇类似物的 CYP1 活化和抗癌特性

  摘要：

  天然存在的二苯乙烯类化合物，如 （E）-二苯乙烯类白藜芦醇和 （Z）-二苯乙烯类化合物 combretastatin A4，已被认为是开发抗癌药物的有前途的先导化合物。已知二苯乙烯类化合物的抗肿瘤特性受细胞色素 P450 酶 CYP1A1 和 CYP1B1 的调节，这有助于肝外 I 期外源性物质和药物代谢。合成白藜芦醇的 34 种甲基醚类似物，并在一组人乳腺细胞系上使用 MTT 细胞增殖测定评估其抗癌特性。表达 CYP1 的乳腺肿瘤细胞系比不具有 CYP1 活性的细胞系受白藜芦醇类似物的影响明显更强。使用分离的 CYP1 酶的代谢研究提供了进一步的证据，证明 （E）-二苯乙烯类化合物可以成为这些酶的底物。通过与合成标准品和 LC-MS 共洗脱研究进行比较来确认代谢产物的结构。最有前途的二苯乙烯类化合物是 （E）-4,3′，4′，5′-四甲氧基二苯乙烯 （DMU212）。该化合物本身显示出低至中度的细胞毒性，但在

  DOI：

  10.3390/molecules29020423

文献信息

• Asymmetric synthesis, stereochemistry and rearrangement reactions of naturally occurring 7′-hydroxylignano-9,9′-lactones
  作者：Barbara Raffaelli、Kristiina Wähälä、Tapio Hase

  DOI：10.1039/b513303c

  日期：——

  The asymmetric synthesis of a series of (7'S,8R,8'R)-7'-hydroxylignano-9,9'-lactones is presented, among them the mammalian lignan (7'S)-hydroxyenterolactone and (7'S)-parabenzlactone, allowing the stereochemistry of natural occurring (-)-parabenzlactone to be re-assigned. A hydroxylactone rearrangement and its possible mechanisms are discussed. Finally a brief survey of the current naming and numbering

  提出了一系列（7'S，8R，8'R）-7'-hydroxylignano-9,9'-内酯的不对称合成，其中包括哺乳动物的木脂素（7'S）-羟基对映体内酯和（7'S）-对羟基苯甲酸酯。天然存在的（-）-对羟基苯甲酸酯的立体化学有待重新分配。羟基内酯重排及其可能的机制进行了讨论。最后，简要介绍了7'-羟基木质素-9,9'-内酯的当前命名和编号变体，并提出了统一术语的建议。
• A Ramberg–Bäcklund route to the stilbenoid anti-cancer agents combretastatin A-4 and DMU-212
  作者：James E. Robinson、Richard J. K. Taylor

  DOI：10.1039/b702411h

  日期：——

  A concise route to combretastatin A-4, a potent inhibitor of tubulin polymerisation, using a Ramberg–Bäcklund reaction to form the key (Z)-stilbene unit has been developed; this Ramberg–Bäcklund approach has also been extended to prepare the (E)-stilbene DMU-212, which also possesses interesting growth inhibitory properties.

  已经开发出一种简洁的途径来合成可瑞替丁A-4，这是一种强效的微管蛋白聚合抑制剂，利用Ramberg-Backlund反应形成关键的（Z）-二苯乙烯单元；这种Ramberg-Backlund方法还被扩展用于制备（E）-二苯乙烯DMU-212，后者也具有令人感兴趣的生长抑制特性。
• Discovery of 8-Cyclopentyl-2-[4-(4-methyl-piperazin-1-yl)-phenylamino]-7-oxo-7,8-dihydro-pyrido[2,3-<i>d</i>]pyrimidine-6-carbonitrile (<b>7x</b>) as a Potent Inhibitor of Cyclin-Dependent Kinase 4 (CDK4) and AMPK-Related Kinase 5 (ARK5)
  作者：M. V. Ramana Reddy、Balireddy Akula、Stephen C. Cosenza、Saikrishna Athuluridivakar、Muralidhar R. Mallireddigari、Venkat R. Pallela、Vinay K. Billa、D. R. C. Venkata Subbaiah、E. Vijaya Bharathi、Rodrigo Vasquez-Del Carpio、Amol Padgaonkar、Stacey J. Baker、E. Premkumar Reddy

  DOI：10.1021/jm401073p

  日期：2014.2.13

  The success of imatinib, a BCR-ABL inhibitor for the treatment of chronic myelogenous leukemia, has created a great impetus for the development of additional kinase inhibitors as therapeutic agents. However, the complexity of cancer has led to recent interest in polypharmacological approaches for developing multikinase inhibitors with low toxicity profiles. With this goal in mind, we analyzed more than 150 novel cyano pyridopyrimidine compounds and identified structure-activity relationship trends that can be exploited in the design of potent kinase inhibitors. One compound, 8-cyclopentyl-2[-4-(4-methyl-piperazin-l-yl)-phenylamino]-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidine-6-carbonitrile (7x), was found to be the most active, inducing apoptosis of tumor cells at a concentration of approximately 30-100 nM. In vitro kinase profiling revealed that 7x is a multikinase inhibitor with potent inhibitory activity against the CDK4/CYCLIN D1 and ARKS kinases. Here, we report the synthesis, structure-activity relationship, kinase inhibitory profile, in vitro cytotoxicity, and in vivo tumor regression studies by this lead compound.
• Synthesis of the Potent Anticancer Agents Ottelione A and Ottelione B in Both Racemic and Natural Optically Pure Forms
  作者：Derrick L. J. Clive、Dazhan Liu

  DOI：10.1021/jo702635t

  日期：2008.4.1

  The powerful antitumor agents ottelione A and B were synthesized in racemic form by a method that relies on selective ring closing metathesis. Optically pure natural (+)-ottelione A was then made from D-ribose, via an alpha-keto cyclopropane. A key feature of the route is that the cyclopropyl group controls the stereochemistry in the attachment of the ArCH2 unit and is then converted by the action of SmI2 into a vinyl group, so that the substituents on the resulting five-membered ring have the required trans relationship. Epimerization of an intermediate gave access, by the same method to the trans ring fused isomer (-)-ottelione B.
• Antineoplastic agents. 113. Synthesis of natural (-)-combretastatin
  作者：George R. Pettit、Sheo Bux Singh、Gordon M. Cragg

  DOI：10.1021/jo00218a032

  日期：1985.9