4,4-diphenylbutyraldehyde | 38151-56-3

• 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: 4,4-diphenylbutyraldehyde
• 英文别名: 4,4-diphenyl butyraldehyde；Diphenylaethylacetaldehyd；4,4-diphenylbutanal
• CAS: 38151-56-3
• 化学式: C₁₆H₁₆O
• 分子量: 224.302
• InChiKey: JYYLMHVNQXZJHJ-UHFFFAOYSA-N

物化性质

• 沸点：
  133 °C(Press: 0.8 Torr)
• 密度：
  1.036±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4,4-diphenylbutyraldehyde 在 1,4-二氧六环 、 溴 作用下， 以 乙醚 为溶剂， 生成 2-bromo-4,4-diphenylbutanal
  参考文献：
  名称：

  Synthesis and structure-activity of 4(5)-(2,2-diphenylethyl)imidazoles as new α2-adrenoreceptor antagonists

  摘要：

  DOI：

  10.1016/0223-5234(90)90180-b
• 作为产物：
  描述：

  4,4-二苯基丁腈 在 二异丁基氢化铝 、 水 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以89%的产率得到4,4-diphenylbutyraldehyde
  参考文献：
  名称：

  烯烃的无金属对映选择性氧化芳构化：高价碘促进的氧化碳键形成

  摘要：

  （E）-6-芳基-1-甲硅烷基氧合己烯-3-烯的对映选择性氧化芳基是在三氟化硼二乙基醚化物存在下使用基于乳酸酯的手性高价碘（III）试剂实现的。甲硅烷基醚促进氧化环化，并增强对映选择性。另外，实现了相应的氨基芳基化。

  DOI：

  10.1002/anie.201609110

文献信息

• Synthesis and Biological Activity of New 3-Hydroxy-3-methylglutaryl Coenzyme A (HMG-CoA) Synthase Inhibitors: 2-Oxetanones with a Side Chain Mimicking the Folded Structure of 1233A.
  作者：Hirokazu HASHIZUME、Hajime ITO、Kohji YAMADA、Hajime NAGASHIMA、Munefumi KANAO、Hiroshi TOMODA、Toshiaki SUNAZUKA、Hidetoshi KUMAGAI、Satoshi OMURA

  DOI：10.1248/cpb.42.512

  日期：——

  To mimic the folded side chain conformation of 1233A (1), which is a 3-hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) synthase inhibitor, 1233A analogs with aromatic rings in the side chain were synthesized. The 2-oxetanone moiety was kept intact. Among 1233A and its synthetic analogs, trans-3-hydroxymethyl-4-[2-(7-methoxycarbonyl-1-naphthyl)ethyl]-2-oxetanone (23) showed the highest HMG-CoA synthase inhibitory activity in vitro. The structure-activity relationship at the side chain is discussed.

  为模拟1233A（1）的折叠侧链构象，该化合物是一种3-羟基-3-甲基戊二酰辅酶A（HMG-CoA）合酶抑制剂，合成了侧链含有芳环的1233A类似物。其中2-恶坦酮部分保持不变。在1233A及其合成类似物中，反式-3-羟甲基-4-[2-(7-甲氧羰基-1-萘基)乙基]-2-恶坦酮（23）显示了最高的HMG-CoA合酶体外抑制活性。讨论了侧链上的构效关系。
• (2S,4S)-2-Amino-4-(2,2-diphenylethyl)pentanedioic acid selective group 2 metabotropic glutamate receptor antagonist
  作者：Ana Escribano、Jesus Ezquerra、Concepción Pedregal、Almudena Rubio、Belén Yruretagoyena、S.Richard Baker、Rebecca A. Wright、Bryan G. Johnson、Darryle D. Schoepp

  DOI：10.1016/s0960-894x(98)00091-2

  日期：1998.4

  (2S,4S)-2-Amino-4-(4,4-diphenylbut-1-yl)-pentane-1,5-dioic acid 1m, is a novel metabotropic glutamate receptor (mGluR) antagonist with insignificant ionotropic affinity. It is selective antagonist of negatively-coupled cAMP-linked mGluRs with no effect on phosphoinositide coupled mGluRs. A series of 4-substituted glutamic acid analogues were prepared and it was found that compound 1k is tenfold more

  （2S，4S）-2-氨基-4-（4,4-二苯基丁-1-基）-戊烷-1,5-二酸1m，是一种新型的代谢型谷氨酸受体（mGluR）拮抗剂，离子亲和力微不足道。它是负偶联cAMP连接的mGluR的选择性拮抗剂，对磷酸肌醇偶联的mGluR没有影响。制备了一系列的4-取代的谷氨酸类似物，发现化合物1k的效力是1m的十倍。化合物1k对离子型谷氨酸受体没有明显的亲和力，第1组和第3组代谢型受体也没有。
• Method of preparing optically active homo-beta-amino acids
  申请人：MONSANTO COMPANY

  公开号：EP0561758A3

  公开（公告）日：1995-04-05

  The present invention is directed to synthesis of homo-β-amino acids of an optical purity sufficient to exhibit optical activity wherein Curtius rearrangement of 3-mono-substituted succinate acid half ester of an optical purity sufficient to exhibit optical activity is affected and the incipient isocyanate is trapped with a primary or secondary alcohol. The resulting carbamate-protected homo-β-amino esters are then saponified to produce the corresponding carbamate-protected homo-β-amino acids which are deprotected to yield homo-β-amino acids of an optical purity sufficient to exhibit optical activity.

  本发明旨在合成具有足够光学活性以表现光学活性的同型β-氨基酸，其中影响了具有足够光学活性的3-单取代琥珀酸半酯的Curtius重排，并且初级异氰酸酯被一级或二级醇捕获。然后，产生的羰基保护的同型β-氨基酸酯被皂化以产生相应的羰基保护的同型β-氨基酸，然后去保护以产生具有足够光学活性以表现光学活性的同型β-氨基酸。
• Synthesis of new 13-diphenylalkyl analogues of berberine and elucidation of their base pair specificity and energetics of DNA binding
  作者：Debipreeta Bhowmik、Franco Buzzetti、Gaetano Fiorillo、Fabrizio Orzi、Tanjia Monir Syeda、Paolo Lombardi、Gopinatha Suresh Kumar

  DOI：10.1039/c3md00254c

  日期：——

  A series of 13-diphenylalkyl berberine derivatives were designed and synthesized, and their base specificity and energetics of DNA binding were evaluated using one natural and two synthetic DNA polynucleotides. Biophysical evaluation demonstrated that the addition of the diphenylalkyl chain at the 13-position of berberine significantly improved the binding ability to DNA. The binding clearly revealed the high preference of the analogues to the alternating AT sequences compared to the alternating GC sequences. The binding affinity was enhanced with the increase in chain length up to a critical length of (CH2)3 in all the cases, after which the binding affinity decreased. Analogue BR4 had the best affinity for DNA, which corresponds to a length of (CH2)3. The results also suggested the adenine-thymine (AT) base specificity of these berberine analogues and that the length of the side chain at the 13-position of the isoquinoline chromophore is critical in modulating the binding affinity.

  设计并合成了一系列 13-二苯基烷基小檗碱衍生物，并使用一种天然 DNA 多核苷酸和两种合成 DNA 多核苷酸评估了它们的碱基特异性和 DNA 结合能。生物物理评估结果表明，在小檗碱的 13 位添加二苯基烷基链可显著提高与 DNA 的结合能力。结合结果清楚地表明，与交替的 GC 序列相比，类似物更倾向于交替的 AT 序列。在所有情况下，结合亲和力随着链长的增加而增强，直到临界长度（CH2）3，之后结合亲和力下降。结果还表明，这些小檗碱类似物具有腺嘌呤-胸腺嘧啶（AT）碱基特异性，异喹啉发色团 13 位侧链的长度是调节结合亲和力的关键。
• Solution and Solid-State Analysis of Binding of 13-Substituted Berberine Analogues to Human Telomeric G-quadruplexes
  作者：Marta Ferraroni、Carla Bazzicalupi、Francesco Papi、Gaetano Fiorillo、Luis Miguel Guamán-Ortiz、Alessio Nocentini、Anna Ivana Scovassi、Paolo Lombardi、Paola Gratteri

  DOI：10.1002/asia.201600116

  日期：2016.4.5

  showing the ligand which interacts via π‐stacking, sandwiched at the interface of two symmetry‐related quadruplex units, with its benzhydryl group contributing to the overall stability of the adduct by means of additional π‐stacking interactions with the DNA residues. The berberine derivatives were also investigated for their cytotoxic activity towards a panel of human cancer cell lines. Compounds NAX042

  通过光谱学和晶体学方法研究了13-苯基烷基和13-二苯基烷基小t碱衍生物（NAX）与人类端粒DNA G4结构之间的相互作用。NAX042和NAX053是改善天然小precursor碱前体性能的最佳化合物。这一发现与NAX053的X射线衍射结果一致‐Tel12加合物，显示通过π堆积相互作用的配体，夹在两个对称相关四链体单元的界面上，其苯甲基通过与DNA残基的额外π堆积相互作用而有助于加合物的整体稳定性。还研究了小ber碱衍生物对一组人类癌细胞系的细胞毒活性。化合物NAX042和NAX053以剂量依赖的方式影响癌细胞系的生存能力。