3,4-二(叔-丁基二甲基硅烷基氧基)苯甲醛 | 99815-16-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3,4-二(叔-丁基二甲基硅烷基氧基)苯甲醛
• 中文别名: 3,4-双(叔丁基二甲硅氧基)苯甲醛
• 英文名称: 3,4-bis(tert-butyldimethylsilanyloxy)benzaldehyde
• 英文别名: 3,4-bis-(tert-butyldimethylsilyloxy)-benzaldehyde；3,4-di(tert-butyldimethylsilyloxy)benzaldehyde；3,4-bis(tert-butyldimethylsiloxy)benzaldehyde；3,4-Di(t-butyldimethylsiloxy)benzaldehyde；3,4-bis[[tert-butyl(dimethyl)silyl]oxy]benzaldehyde
• CAS: 99815-16-4
• 化学式: C₁₉H₃₄O₃Si₂
• 分子量: 366.648
• InChiKey: OTENVZJLWMQSAT-UHFFFAOYSA-N

物化性质

• 熔点：
  36-38 °C
• 沸点：
  369.9±32.0 °C(Predicted)
• 密度：
  0.950±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.27
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,4-二(叔-丁基二甲基硅烷基氧基)苯甲醛 在 正丁基锂 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 18.08h， 生成 白皮杉醇
  参考文献：
  名称：

  芪木脂素 Aiphanol 和三种同系物的外消旋修饰的仿生制备

  摘要：

  通过银 (I) 介导和潜在的仿生氧化偶联生成二苯乙烯木脂素 (–)-aiphanol 的外消旋修饰体 (±)-1 和同系物 (±)-2–4 的色谱分离混合物(5) 与芥子醇 (6)。

  DOI：

  10.1071/ch07044
• 作为产物：
  描述：

  香草醛 在 咪唑 、 三溴化硼 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 3,4-二(叔-丁基二甲基硅烷基氧基)苯甲醛
  参考文献：
  名称：

  Novel multifunctional dopamine D 2 /D 3 receptors agonists with potential neuroprotection and anti-alpha synuclein protein aggregation properties

  摘要：

  Our ongoing drug development endeavor to design compounds for symptomatic and neuroprotective treatment of Parkinson's disease (PD) led us to carry out a structure activity relationship study based on dopamine agonists pramipexole and 5-OHDPAT. Our goal was to incorporate structural elements in these agonists in a way to preserve their agonist activity while producing inhibitory activity against aggregation of alpha-synuclein protein. In our design we appended various catechol and related phenol derivatives to the parent agonists via different linker lengths. Structural optimization led to development of several potent agonists among which (-)-8a, (-)-14 and (-)-20 exhibited potent neuroprotective properties in a cellular PD model involving neurotoxin 6-OHDA. The lead compounds (-)-8a and (-)-14 were able to modulate aggregation of alpha-synuclein protein efficiently. Finally, in an in vivo PD animal model, compound (-)-8a exhibited efficacious anti-parkinsonian effect. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.08.021

文献信息

• Total synthesis of artochamins F, H, I, and J through cascade reactions
  作者：K.C. Nicolaou、Troy Lister、Ross M. Denton、Christine F. Gelin

  DOI：10.1016/j.tet.2008.02.108

  日期：2008.5

  A concise and efficient cascade-based total synthesis of artochamins F, H, I, and J is described. The potential biogenetic connection between artochamin F, or a derivative thereof, and artochamins H, I, and J, through an unusual formal [2+2] cycloaddition process, was shown to be feasible. An alternative mechanism for this transformation is also proposed.

  描述了一种简洁高效的基于级联的 artchamins F、H、I 和 J 的全合成。通过不寻常的正式 [2+2] 环加成过程，artchamin F 或其衍生物与 artchamin H、I 和 J 之间的潜在生物遗传联系被证明是可行的。还提出了这种转换的替代机制。
• Direct Alkynylation of 3<i>H</i>-Imidazo[4,5-<i>b</i>]pyridines Using <i>gem</i>-Dibromoalkenes as Alkynes Source
  作者：Jessy Aziz、Tom Baladi、Sandrine Piguel

  DOI：10.1021/acs.joc.6b00406

  日期：2016.5.20

  C2 direct alkynylation of 3H-imidazo[4,5-b]pyridine derivatives is explored for the first time. Stable and readily available 1,1-dibromo-1-alkenes, electrophilic alkyne precursors, are used as coupling partners. The simple reaction conditions include an inexpensive copper catalyst (CuBr·SMe2 or Cu(OAc)2), a phosphine ligand (DPEphos) and a base (LiOtBu) in 1,4-dioxane at 120 °C. This C–H alkynylation

  首次探索了3 H-咪唑并[4,5- b ]吡啶衍生物的C2直接炔基化。稳定且易于获得的1,1-二溴-1-烯烃（亲电炔前体）用作偶联伙伴。简单的反应条件包括：廉价的铜催化剂（CuBr·SMe 2或Cu（OAc）2），膦配体（DPEphos）和1,4-二恶烷中的碱（LiO t Bu）在120°C的条件下。该C-H炔基化方法显露是与各种上两个耦合伙伴取代的兼容：杂芳烃和宝石-dibromoalkenes。该协议可以直接合成各种2-炔基-3 H-咪唑并[4,5- b]吡啶，一种在药物设计中有价值的支架。
• The design, synthesis and biological evaluation of pro-EGCG derivatives as novel anti-vitiligo agents
  作者：Siyu Wang、Rong Jin、Ruiquan Wang、Yongzhou Hu、Xiaowu Dong、Ai e Xu

  DOI：10.1039/c6ra23172a

  日期：——

  A series of prodrugs of EGCG derivatives were designed, synthesized, and the protective effect on melanocytes against H₂O₂-induced cell damage were extensively evaluated, demonstrating the potential application value of them in anti-vitiligo treatment.

  一系列EGCG衍生物的前药被设计、合成，并对其在对抗H₂O₂诱导的黑色素细胞损伤中的保护效果进行了广泛评估，展示了它们在抗白癜风治疗中的潜在应用价值。
• Design, synthesis, and discovery of stilbene derivatives based on lithospermic acid B as potent protein tyrosine phosphatase 1B inhibitors
  作者：Mankil Jung、Yongnam Lee、Moonsoo Park、Hanjo Kim、Heekyeong Kim、Eunyoung Lim、Jungae Tak、Minjoo Sim、Dongeun Lee、Namsoo Park、Won Keun Oh、Kyu Yeon Hur、Eun Seok Kang、Hyun-Chul Lee

  DOI：10.1016/j.bmcl.2007.06.016

  日期：2007.8

  Dihydroxy stilbene derivatives were designed based on lithospermic acid B and were prepared from 4-(chloromethyl)benzoic acid. The inhibitory activities of the novel compounds against protein tyrosine phosphatase 1B (PTP1B) were evaluated. 3,4-Dihydroxy stilbene carbonyl compounds (7, 11b, 27b) inhibited PTP1B with IC50 values comparable to molybdate, while the conjugation-extended compound (15b) showed

  二羟基二苯乙烯衍生物是基于精酸B设计的，由4-(氯甲基)苯甲酸制备。评估了新化合物对蛋白酪氨酸磷酸酶 1B (PTP1B) 的抑制活性。3,4-二羟基芪羰基化合物 (7, 11b, 27b) 抑制 PTP1B 的 IC50 值与钼酸盐相当，而缀合扩展化合物 (15b) 的抑制作用比临床前 RK682 高 3 倍。将吸电子基团或酰胺引入第二个苯环，或将共轭延伸到二苯乙烯分子中，可以提高生成自由基的稳定性。
• Straightforward Synthesis of Highly Hydroxylated Phloroglucinol-Type 3-Deoxyanthocyanidins
  作者：Stefan Chassaing、Marie Kueny-Stotz、Géraldine Isorez、Raymond Brouillard

  DOI：10.1055/s-2007-977442

  日期：——

  Phloroglucinol-type 3-deoxyanthocyanidins were synthesized through the interaction between phloroglucinol derivatives and arylethynylketones in acetic acid in the presence of aqueous hexafluorophosphoric acid. This methodology was applied to achieve the synthesis of natural apigeninidin, luteolinidin and ­tricetanidin with high yields.

  通过在含水的六氟磷酸存在下，醋酸中根皮酚衍生物与芳基乙炔酮的反应，合成了根皮酚型的3-脱氧花青素。该方法被成功应用于以高产率合成天然产物芹菜素苷、黄芩素苷和三萜苷。