(3S)-3-(tert-butyldimethylsilanyloxy)-3-(4-nitrophenyl)propionaldehyde | 494803-26-8

• 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: (3S)-3-(tert-butyldimethylsilanyloxy)-3-(4-nitrophenyl)propionaldehyde
• 英文别名: (S)-3-((tert-butyldimethylsilyl)oxy)-3-(4-nitrophenyl)propanal
• CAS: 494803-26-8
• 化学式: C₁₅H₂₃NO₄Si
• 分子量: 309.437
• InChiKey: VPSHFVQEJDAFAB-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.25
• 重原子数：
  21.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  69.44
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (3S)-3-(tert-butyldimethylsilanyloxy)-3-(4-nitrophenyl)propionaldehyde 在 4-二甲氨基吡啶 、 四丁基氟化铵 、 N,N'-二异丙基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 22.0h， 生成 (S,E)-tert-butyl 5-{((6R,13S)-13-isobutyl-6-(4-methoxybenzyl)-2,2-dimethyl-4,7,11-trioxo-3,12-dioxa-5,8-diazatetradecan-14-oyl)oxy}-5-(4-nitrophenyl)pent-2-enoate
  参考文献：
  名称：

  Design and synthesis of a new class of cryptophycins based tubulin inhibitors

  摘要：

  Tubulin binding compounds represent one of the most attractive targets for anticancer drug development. They broadly fall into two categories viz., tubulin polymerization inhibitors, which block microtubule growth and destabilize microtubules like vinca alkaloids and cryptophycins, and the others, which polymerize microtubules into hyperstable forms represented by family of taxanes. In this context, we aimed at design and synthesis of cryptophycins based macrocyclic depsipeptides, which are synthetically more accessible, however have the basic information to target tubulins and establish structure activity relationship (SAR). Thus, a new class of cryptophycins based marocyclic depsipeptides with a truncated epoxide chain were synthesized as potential tubulin inhibitors. The resultant lead analogues 15a and 16a exhibited good anti-cancer activity, induced apoptosis, caused block/delay in cell cycle as well as significantly reduced the expression of alpha- and beta-tubulins. Molecular modelling studies show that 15a and 16a bind in the same domain as that of cryptophycins. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.11.068
• 作为产物：
  描述：

  (3'S,4S)-4-benzyl-3-[3'-hydroxy-3'-(4-nitrophenyl)propionyl]oxazolidin-2-one 在 咪唑 、 三甲基铝 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 4.75h， 生成 (3S)-3-(tert-butyldimethylsilanyloxy)-3-(4-nitrophenyl)propionaldehyde
  参考文献：
  名称：

  Asymmetric synthesis of aldol products derived from unsymmetrical ketones: assignment of the absolute configuration of antibody aldol products

  摘要：

  Compounds 1-7 are the products formed by aldol condensation of p-nitrobenzaldehyde with a series of unsymmetrical ketones, the reaction occurring at the less substituted carbon. The asymmetric synthesis of 1-7 using the Evans's asymmetric aldol methodology is described in detail. These syntheses were completed to allow us to assign the absolute configuration of products 1-3, obtained in a single step in the presence of the aldolase I antibody 84G3. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00410-x

文献信息

• Synthesis of α,β-Unsaturated δ-Lactones by Vinyl Acetate Mediated Asymmetric Cross-Aldol Reaction of Acetaldehyde: Mechanistic Insights
  作者：Manjeet Kumar、Arvind Kumar、Masood Rizvi、Manoj Mane、Kumar Vanka、Subhash C. Taneja、Bhahwal Ali Shah

  DOI：10.1002/ejoc.201402551

  日期：2014.8

  using this methodology we have accessed α,β-unstaurated δ-lactones as well as isochromenones with high enantioselectivities from both asymmetric β-hydroxy aldehydes and ketones. Systemic density functional theory (DFT) studies were also performed to gain mechanistic insights into the role of hydrogen bonding in the asymmetric cross-aldol reaction of acetaldehyde and in the key cis/trans isomerisation

  已经开发了涉及从乙酸乙烯酯原位生成乙醛的串联不对称交叉羟醛反应，可以解决与乙醛处理相关的挑战。简单的方案、温和的反应条件以及有机催化剂与生物催化剂的独特协调，使该方法成为合成不对称 β-羟基醛的宝贵工具。通过使用这种方法，我们从不对称 β-羟基醛和酮中获得了具有高对映选择性的 α,β-不饱和 δ-内酯以及异色酮。还进行了系统密度泛函理论 (DFT) 研究，以深入了解氢键在乙醛的不对称交叉羟醛反应和 δ-内酯合成中的关键顺/反异构化步骤中的作用。