1-bromo-2,4-dimethoxy-6-(t-butyldimethylsilyloxy)methylbenzene | 166533-30-8

• 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: 1-bromo-2,4-dimethoxy-6-(t-butyldimethylsilyloxy)methylbenzene
• 英文别名: tert-butyl<(2-bromo-3,5-dimethoxybenzyl)oxy>dimethylsilane；1-<(tert-Butyldimethylsilyloxy)methyl>-2-bromo-3,5-dimethoxybenzene；(2-Bromo-3,5-dimethoxyphenyl)methoxy-tert-butyl-dimethylsilane
• CAS: 166533-30-8
• 化学式: C₁₅H₂₅BrO₃Si
• 分子量: 361.351
• InChiKey: SNBYGQYEZQXYAT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.99
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-bromo-2,4-dimethoxy-6-(t-butyldimethylsilyloxy)methylbenzene 在 吡啶 、 Amberlite IR-120 、 叔丁基锂 作用下， 反应 31.5h， 生成 1,1²-anhydro-1-C-<2-(hydroxymethyl)-4,6-dimethoxyphenyl>-β-D-glucopyranose tetraacetate
  参考文献：
  名称：

  Total Synthesis and Structural Elucidation of the Antifungal Agent Papulacandin D

  摘要：

  Condensation of the aryllithium reagents, prepared from the bromides 10 and 11 and tert-butyllithium, with lactone 19 and acid-catalyzed spirocyclization gave the papulacandin spiroketals 14 and 15. Subsequent protection using di-tert-butylsilyl bis(trifluoromethanesulfonate) gave the diols 31 and 30. Isoleucine (37) was converted using a double Wittig reaction sequence and propargylation of the intermediate aldehyde 46 into the alkynol 47. Separation of the C-7 epimers of 47 was achieved using kinetic resolution via Sharpless epoxidation. Both alkynol epimers 53 and 57 were converted into the papulacandin side chain esters 65 and 66 using a hydrozirconation and palladium(0)-catalyzed coupling sequence. Comparisons of Mosher ester derivatives of 65 and 66 with the Mosher ester derivative of the natural papulacandin side chain and further degradation were consistent with the stereochemistry of the natural product being 7S,14S. Esterification of the spiroketals with the mixed anhydride 70 and global deprotection gave papulacandin D (1).

  DOI：

  10.1021/jo951895e
• 作为产物：
  描述：

  3,5-二甲氧基苯甲酸甲酯 在 咪唑 、 N-溴代丁二酰亚胺(NBS) 、 lithium aluminium tetrahydride 作用下， 生成 1-bromo-2,4-dimethoxy-6-(t-butyldimethylsilyloxy)methylbenzene
  参考文献：
  名称：

  三唑取代生物活性二苯乙烯中的中心烯烃

  摘要：

  芪部分常见于天然产物中，这些化合物显示出非凡的生物活性。从二苯乙烯中提取有用药物的努力必须解决这种结构的潜在问题，包括顺式/反式异构化的倾向。为了确定在保持生物活性的同时解决这一限制的烯烃替代物，我们制备了两种生物活性二苯乙烯的类似物，一种爪胡斯金和一种施韦因富辛，其中 1,2,3-三唑环正式取代了二苯乙烯双键。新的 schweinfurthin 类似物 ( 23 ) 已针对 60 种细胞系进行了抗增殖活性测试，与激发其合成的化合物 ( 22 ) 相比，它显示出强烈的生物活性相关性。

  DOI：

  10.1016/j.bmcl.2022.128980

文献信息

• Formal Synthesis of Both Atropomers of Desertorin C and an Example of Chirality Transfer from a Biphenyl Axis to a Spiro Centre and its Reverse
  作者：Robert W. Baker、Rekha V. Kyasnoor、Melvyn V. Sargent、Brian W. Skelton、Allan H. White

  DOI：10.1071/ch99134

  日期：——

  crystal X-raystructural determination. The similar product(S,4S)-2-(2′,4′,6-trimethoxy-4,6′-dimethyl-1,1′-biphenyl-6-yl)-4,5-dihydrooxazole(43) was converted into(S)-1-(2,4′,6′-trimethoxy-4,6′-biphenyl-2-yl)ethanone(57) which furnished(S)-1-(2′,4′,6-trimethoxy-4,6′-dimethyl-1,1′-biphenyl-2-yl)acetamide(58) (43%) and(S)-2,7′-dimethoxy-3′,5′,6-trimethylspiro[cyclohexa-2,5-diene-1,1′-(1H)isoindole]-4-one(61)

  关于对映体纯形式的 4,4',7,7'-四甲氧基-5,5'-二甲基-6,8'-双香豆素 (desertorin C) (11) 的合成，反应产物的非对映体比例2-异丙氧基-6-甲氧基-4-甲基苯基溴化镁(24)和(4S)-4-异丙基-2-(2,3,5-三甲氧基苯基)-4,5-二氢恶唑(23)，介于2,4-之间二甲氧基-6-甲基苯基溴化镁(37)和(4S)-4-异丙基-2-(2,3-二甲氧基-5-甲基苯基)-4,5-二氢恶唑(36)和2,4-二甲氧基-6-之间探索了（叔丁基二甲基甲硅烷氧基）甲基苯基溴化镁（46）和恶唑（36）。最后提到的反应的主要产物转化为(S,4S)-4-isopropyl-2-(2'-hydroxymethyl-4',6,6'-trimethoxy-4-methyl-1,1'-biphenyl-6 -yl)-4,5-dihydroxazole(49)，其轴向构型通过单晶
• Efficient synthesis of 5-aryl-2-vinylfurans by palladium catalyzed cross-coupling strategies
  作者：Devan Balachari、Liam Quinn、George A. O'Doherty

  DOI：10.1016/s0040-4039(99)00817-5

  日期：1999.6

  The synthesis of substituted 5-aryl-2-furfurals from furfural by three alternative palladium cross coupling strategies are described. The resulting 5-aryl-2-furfurals were converted into their corresponding 5-aryl-2-vinylfurans in good yields by Wittig chemistry, (C) 1999 Elsevier Science Ltd. All rights reserved.
• Formal Synthesis of (-)-O-Methylancistrocladine
  作者：Brent N. Leighton、Mark A. Rizzacasa

  DOI：10.1021/jo00122a067

  日期：1995.9
• Total Synthesis and Structural Elucidation of the Antifungal Agent Papulacandin D
  作者：Anthony G. M. Barrett、Michael Peña、J. Adam Willardsen

  DOI：10.1021/jo951895e

  日期：1996.1.1

  Condensation of the aryllithium reagents, prepared from the bromides 10 and 11 and tert-butyllithium, with lactone 19 and acid-catalyzed spirocyclization gave the papulacandin spiroketals 14 and 15. Subsequent protection using di-tert-butylsilyl bis(trifluoromethanesulfonate) gave the diols 31 and 30. Isoleucine (37) was converted using a double Wittig reaction sequence and propargylation of the intermediate aldehyde 46 into the alkynol 47. Separation of the C-7 epimers of 47 was achieved using kinetic resolution via Sharpless epoxidation. Both alkynol epimers 53 and 57 were converted into the papulacandin side chain esters 65 and 66 using a hydrozirconation and palladium(0)-catalyzed coupling sequence. Comparisons of Mosher ester derivatives of 65 and 66 with the Mosher ester derivative of the natural papulacandin side chain and further degradation were consistent with the stereochemistry of the natural product being 7S,14S. Esterification of the spiroketals with the mixed anhydride 70 and global deprotection gave papulacandin D (1).
• Substitution of a triazole for the central olefin in biologically active stilbenes
  作者：David P. Stockdale、John A. Beutler、David F. Wiemer

  DOI：10.1016/j.bmcl.2022.128980

  日期：2022.11

  activity we have prepared analogues of two bioactive stilbenes, a pawhuskin and a schweinfurthin, where a 1,2,3-triazole ring formally replaces the stilbene double bond. The new schweinfurthin analogue (23) has been tested for anti-proliferative activity against 60 cell lines, and shows a strong correlation of bioactivity when compared to the compound that inspired its synthesis (22).

  芪部分常见于天然产物中，这些化合物显示出非凡的生物活性。从二苯乙烯中提取有用药物的努力必须解决这种结构的潜在问题，包括顺式/反式异构化的倾向。为了确定在保持生物活性的同时解决这一限制的烯烃替代物，我们制备了两种生物活性二苯乙烯的类似物，一种爪胡斯金和一种施韦因富辛，其中 1,2,3-三唑环正式取代了二苯乙烯双键。新的 schweinfurthin 类似物 ( 23 ) 已针对 60 种细胞系进行了抗增殖活性测试，与激发其合成的化合物 ( 22 ) 相比，它显示出强烈的生物活性相关性。