2-(benzyloxy)-3-ethoxybenzaldehyde | 131866-67-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(benzyloxy)-3-ethoxybenzaldehyde
• 英文别名: 2-benzyloxy-3-ethoxy-benzaldehyde；3-ethoxy-2-benzyloxy-benzaldehyde；3-Aethoxy-2-benzyloxy-benzaldehyd；2-Benzyloxy-3-ethoxybenzaldehyde；3-ethoxy-2-phenylmethoxybenzaldehyde
• CAS: 131866-67-6
• 化学式: C₁₆H₁₆O₃
• mdl: MFCD07361274
• 分子量: 256.301
• InChiKey: QPOIBFQNRYMSCP-UHFFFAOYSA-N

物化性质

• 熔点：
  39-40 °C
• 沸点：
  185 °C(Press: 1.6 Torr)
• 密度：
  1.132±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.187
• 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：

  2-(benzyloxy)-3-ethoxybenzaldehyde 在 lithium aluminium tetrahydride 、 ammonium acetate 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 2-(2-benzyloxy-3-ethoxy-phenyl)ethylamine
  参考文献：
  名称：

  SAR Based Design of Nicotinamides as a Novel Class of Androgen Receptor Antagonists for Prostate Cancer

  摘要：

  Molecular knowledge of pure antagonism and systematic SAR study offered a direction for structural optimization of DIMN to provide nicotinamides as a novel series of AR antagonists. Nicotinamides with extended linear scaffold bearing sterically bulky alkoxy groups on isoquinoline end were synthesized for H12 displacement AR binding affinity and molecular basis of antiandrogenic effect establish the optimized derivatives, 7au and 7bb, as promising candidates of second generation AR antagonists for advanced prostate cancer.

  DOI：

  10.1021/jm3014103
• 作为产物：
  描述：

  2,3-二羟基苯甲醛 在 caesium carbonate 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 生成 2-(benzyloxy)-3-ethoxybenzaldehyde
  参考文献：
  名称：

  2-(2-Hydroxy-3-alkoxyphenyl)-1H-benzimidazole-5-carboxamidine derivatives as potent and selective urokinase-type plasminogen activator inhibitors

  摘要：

  The development of potent and selective urokinase-type plasminogen activator (uPA) inhibitors based on the lead molecule 2-(2-hydroxy-3-ethoxyphenyl)-1H-benzimidazole-5-carboxamidine (3a) is described. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00311-6

文献信息

• Synthesis and Structure–Activity Relationships of Aristoyagonine Derivatives as Brd4 Bromodomain Inhibitors with X-ray Co-Crystal Research
  作者：Minjin Yoo、Tae Hyun Park、Miyoun Yoo、Yeongrin Kim、Joo-Youn Lee、Kyu Myung Lee、Seong Eon Ryu、Byung Il Lee、Kwan-Young Jung、Chi Hoon Park

  DOI：10.3390/molecules26061686

  日期：——

  Herein, we report the design, synthesis, and X-ray studies of novel aristoyagonine (benzo[6,7]oxepino[4,3,2-cd]isoindol-2(1H)-one) derivatives and investigate their inhibitory effect against Brd4 bromodomain. Five compounds 8ab, 8bc, 8bd, 8be, and 8bf have been discovered with high binding affinity over the Brd4 protein. Co-crystal structures of these five inhibitors with human Brd4 bromodomain demonstrated

  已知表观遗传调节在抗癌治疗的进展中起关键作用。赖氨酸乙酰化是控制基因表达的重要机制。由于溴结构域能够调节各种基因作为表观遗传“阅读器”的转录能力，因此对溴结构域的兴趣日益浓厚。在这里，我们报告新型马兜铃精（苯并[6,7]氧庚啶[4,3,2- cd ]异吲哚-2（1 H）-one）衍生物的设计，合成和X射线研究，并研究其抑制作用反对Brd4 bromodomain。五种化合物8AB，8bc，8bd，8be和8BF已经发现对Brd4蛋白具有高结合亲和力。这五种抑制剂与人Brd4溴结构域的共晶体结构表明，它具有占据疏水口袋的关键结合模式，而疏水口袋被称为乙酰化赖氨酸结合位点。这些新颖的Brd4溴结构域抑制剂显示出令人印象深刻的抑制活性和作用模式，用于治疗癌症。
• A Convenient and Improved Baylis-Hillman Synthesis of 3-Substituted 2<i>H</i>-1-benzopyran-2-ones
  作者：Perry T. Kaye、Musiliyu A. Musa

  DOI：10.1055/s-2002-35984

  日期：——

  Halogen acid-catalysed deprotection and cyclisation of Baylis-Hillman products obtained using O-benzylated salicylaldehyde precursors has been shown to afford 3-(halomethyl)coumarins (3-halomethyl-2H-1-benzopyran-2-ones) chemoselectively and in good yield.

  研究表明，使用 O-苄基水杨醛前体对巴利斯-希尔曼（Baylis-Hillman）产物进行卤酸催化脱保护和环化，可以化学选择性地获得 3-（卤甲基）香豆素（3-卤甲基-2H-1-苯并吡喃-2-酮），而且收率很高。
• Application of Baylis–Hillman Methodology in the Synthesis of Coumarin Derivatives
  作者：Perry T. Kaye、M. A. Musa

  DOI：10.1081/scc-120018937

  日期：2003.1.6

  Abstract A general, chemoselective approach to 3-substituted coumarins via Baylis–Hillman reactions of O-benzylated salicylaldehyde precursors has been demonstrated. Competitive cyclization to chromene derivatives is inhibited by conjugate addition of benzylamine or piperidine to the α,β-unsaturated ester intermediates.

  摘要 已经证明了通过 O-苄基化水杨醛前体的 Baylis-Hillman 反应生成 3-取代香豆素的通用化学选择性方法。苄胺或哌啶与 α,β-不饱和酯中间体的共轭加成抑制了色烯衍生物的竞争性环化。
• Exploring intermolecular contacts in multi-substituted benzaldehyde derivatives: X-ray, Hirshfeld surface and lattice energy analyses
  作者：Siya T. Hulushe、Meloddy H. Manyeruke、Marcel Louzada、Sergei Rigin、Eric C. Hosten、Gareth M. Watkins

  DOI：10.1039/c9ra10752e

  日期：——

  intermolecular C–H⋯O hydrogen bonds. An interplay of C–H⋯O hydrogen bonds, and C–H⋯π and π–π stacking interactions facilitates the formation of multi-dimensional supramolecular networks. Crystal packings in 4 and 5 are further generated by type I halogen⋯halogen bonding interactions. The differences in crystal packing are represented by variation of substitution positions in the compounds. Structure 3 is isomorphous

  六种苯甲醛衍生物 ( 1-6 )的晶体结构已被确定，并通过 X 射线晶体学研究建立了它们的超分子网络。研究表明，这些化合物通过各种分子间相互作用连接在一起，例如弱C-H⋯O氢键、C-H⋯π、π-π和卤素键相互作用，从而巩固和加强了这些分子组装体的形成。羰基通过分子间 C-H⋯O 氢键在1-6中产生不同的合成子。 C-H⋯O氢键的相互作用以及C-H⋯π和π-π堆积相互作用促进了多维超分子网络的形成。4和5中的晶体堆积是通过I型卤素…卤素键相互作用进一步产生的。晶体堆积的差异通过化合物中取代位置的变化来表示。结构3与结构4是同晶的，但它们的晶体堆积方式有细微的差别。通过赫什菲尔德曲面和二维指纹图研究了结构中分子间接触的性质，作为构建不同超分子网络的比较。利用标题化合物和从剑桥结构数据库 (CSD) 检索的各种类似结构的理论计算来量化分子间相互作用能。分子对的分子间相互作用也从各自的晶体结构中提
• Practical Asymmetric Catalytic Synthesis of Spiroketals and Chiral Diphosphine Ligands
  作者：Xubin Wang、Peihua Guo、Xiaoming Wang、Zheng Wang、Kuiling Ding

  DOI：10.1002/adsc.201300380

  日期：2013.10.11

  AbstractA practical procedure has been developed for efficient synthesis of chiral aromatic spiroketals and the relevant diphosphine ligands. The procedure includes first asymmetric hydrogenation of readily available α,α′‐bis(2‐benzyloxyarylidene) ketones catalyzed by the Ir(I)/SpinPHOX (S,S)‐1a (0.5–1 mol%) and subsequent hydrogenative deprotection of the resultant benzyl ethers catalyzed by palladium on carbon (Pd/C), as well as simultaneous spiroketalization of the corresponding diphenolic ketones by (S,S)‐1a in one pot. The corresponding chiral aromatic spiroketals (R,R,R)‐4a–j have been obtained in high yields (77–94%) with good diastereoselectivities (trans/cis=81/19 to 96/4), and excellent enantioselectivities for the trans products (97–>99% ee). In addition, the reaction of aromatic spiroketal difluoride (R,R,R)‐4b with potassiodiarylphosphide (KPAr2) in refluxing tertahydrofuran (THF) has also provided an alternative and practical synthesis of chiral spiroketal‐based diphosphine (SKP) ligands in 78–95% yields on multigram scale.magnified image