4-<(tert-butyldimethylsilyl)oxy>-3-methoxybenzyl bromide | 113931-97-8

• 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: 4-<(tert-butyldimethylsilyl)oxy>-3-methoxybenzyl bromide
• 英文别名: (4-(bromomethyl)-2-methoxyphenoxy)(tert-butyl)dimethylsilane；[4-(Bromomethyl)-2-methoxyphenoxy]-tert-butyl-dimethylsilane
• CAS: 113931-97-8
• 化学式: C₁₄H₂₃BrO₂Si
• 分子量: 331.325
• InChiKey: JMBNNPALKWLAIF-UHFFFAOYSA-N

物化性质

• 沸点：
  333.6±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：

  4-<(tert-butyldimethylsilyl)oxy>-3-methoxybenzyl bromide 在 四丁基氟化铵 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 8.83h， 生成 4-[(E)-2-(4-羟基-3-甲氧基苯基)乙烯基]-2-甲氧基苯酚
  参考文献：
  名称：

  Evaluation of Manassantin A Tetrahydrofuran Core Region Analogues and Cooperative Therapeutic Effects with EGFR Inhibition

  摘要：

  Tumors adapt to hypoxia by regulating angiogenesis, metastatic potential, and metabolism. These adaptations mediated by hypoxia-inducible factor 1 (HIF-1) make tumors more aggressive and resistant to chemotherapy and radiation. Therefore, HIF-1 is a validated therapeutic target for cancer. In order to develop new HIF-1 inhibitors for cancer chemotherapy by harnessing the potential of the natural product manassantin A, we synthesized and evaluated manassantin A analogues with modifications in the tetrahydrofuran core region of manassantin A. Our structure-activity relationship study indicated that the alpha,alpha'-trans-configuration of the central ring of manassantin A is critical to HIF-1 inhibition. We also demonstrated that a combination of manassantin A with an epidermal growth factor receptor inhibitor shows cooperative antitumor activity (similar to 80% inhibition for combination vs similar to 30% inhibition for monotherapy). Our findings will provide important frameworks for the future therapeutic development of manassantin A-derived chemotherapeutic agents.

  DOI：

  10.1021/acs.jmedchem.0c00151
• 作为产物：
  描述：

  2-甲氧基-4-甲基苯酚 在 咪唑 、 N-溴代丁二酰亚胺(NBS) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 4-<(tert-butyldimethylsilyl)oxy>-3-methoxybenzyl bromide
  参考文献：
  名称：

  Synthesis of α,β-Unsaturated Ketones Using Allylidenetriphenylphosphorane as a Three-carbon Unit

  摘要：

  在碱存在下，3-烷氧羰基-2-乙氧基-2-亚丙烯基三苯基膦通过一锅程序依次与烷基卤化物和醛发生反应，生成中等至高产率的共轭烯醇醚。共轭烯醇醚的水解和随后的脱羧反应提供了一种获得 α、β-不饱和酮的新途径。

  DOI：

  10.1246/cl.1992.2253

文献信息

• Synthesis of a Photo-Caged DOPA Derivative by Selective Alkylation of 3,4-Dihydroxybenzaldehyde
  作者：Tobias Schneider、Vladimir Kubyshkin、Nediljko Budisa

  DOI：10.1002/ejoc.201701749

  日期：2018.5.15

  A general route towards 3‐O‐alkylated DOPA derivatives has been developed. The regioselectivity of the synthesis was controlled by the number of base equivalents in the first alkylation step. In this way a photo‐caged DOPA was prepared that can readily be incorporated into recombinant protein sequences, thus enabling biosynthetic production of light‐activatable bioadhesives.

  已经开发了一种制备3-O-烷基化DOPA衍生物的一般方法。合成的区域选择性由第一烷基化步骤中碱当量的数量控制。这样，制备了光笼装的DOPA，可以将其轻松地掺入重组蛋白序列中，从而能够生物合成生产可光活化的生物粘合剂。
• Chromium–Salen Complex/Nitroxyl Radical Cooperative Catalysis: A Combination for Aerobic Intramolecular Dearomative Coupling of Phenols
  作者：Shota Nagasawa、Shogo Fujiki、Yusuke Sasano、Yoshiharu Iwabuchi

  DOI：10.1021/acs.joc.1c00438

  日期：2021.5.7

  aerobic intramolecular dearomative coupling reaction of tethered phenols using a catalytic system consisting of a chromium–salen (Cr–salen) complex combined with a nitroxyl radical. This novel catalytic system enables formation of various spirocyclic dienone products including those unable to be accessed by previously reported methods efficiently under mild reaction conditions.

  我们描述了使用由铬-salen（Cr-salen）配合物与硝酰基自由基组成的催化体系，使束缚酚的需氧分子内脱芳香反应。这种新颖的催化系统能够在温和的反应条件下有效地形成各种螺环二烯酮产物，包括那些以前报道的方法无法有效利用的产物。
• Photochemistry of a model lignin compound. Spin trapping of primary products and properties of an oligomer
  作者：L.R.C. Barclay、G.R. Cromwell、J.W. Hilborn

  DOI：10.1139/v94-007

  日期：1994.1.1

  for photolysis and free radical spin trapping studies. The 3,4-dimethoxyphenacyl radical, Ar-COĊH2, 2, thermally generated from α-bromoacetoveratrone with trimethyltin, was spin trapped by phenyl-tert-butylnitrone (PBN), and the spin-trapped radical identified by ESR and mass spectroscopy. Spin trapping by PBN of radical photoproducts from 1 gave a mixture of trapped radicals, according to ESR. These

  α-愈创木酚乙酸酯酮 1 被选为木质素结构组分的模型，用于光解和自由基自旋捕获研究。3,4-二甲氧基苯甲酰基自由基 Ar-COĊH2, 2 由 α-溴乙酰丙酮与三甲基锡热生成，被苯基-叔丁基硝酮 (PBN) 自旋捕获，自旋捕获自由基由 ESR 和质谱鉴定。根据 ESR，PBN 对来自 1 的自由基光产物的自旋捕获产生了被捕获自由基的混合物。它们被分离为羟胺，并在化学电离 (CI) 条件下通过液相色谱/质谱 (LC/MS) 进行鉴定。这种 LC/MS (CI) 方法鉴定了相同的苯甲酰基片段 2（还原），以及暂时归因于自旋捕获的愈创木酚自由基的片段，化学还原为羟胺。1 的扩展直接光解产生有色顺磁性低聚物。1-(3,4-二甲氧基苯基)-2-(4-羟基-3-甲氧基苯基乙酮(10)的合成，一种重排、重组...
• Enantioselective Synthesis of Imperanene, a Platelet Aggregation Inhibitor
  作者：James C. Shattuck、Cheney M. Shreve、Sandra E. Solomon

  DOI：10.1021/ol0164482

  日期：2001.9.1

  Both enantiomers of imperanene, a platelet aggregation inhibitor, have been synthesized in 82-90% ee. The key step of establishing the chiral center was achieved through stereoselective alkylation with benzyl chloromethyl ether using Enders' RAMP/SAMP chiral auxiliary method. The natural product was determined to be the (S)-enantiomer through comparison of optical rotation data. Reaction: see text

  戊二烯（一种血小板聚集抑制剂）的两种对映体均以82-90％ee的比例合成。建立手性中心的关键步骤是通过使用Enders的RAMP / SAMP手性辅助方法与苄基氯甲基醚进行立体选择性烷基化来实现的。通过旋光度数据的比较确定天然产物为（S）-对映体。反应：见文字。
• 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。