3-(苯基甲氧基)-苯丙醛 | 75677-04-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 3-(苯基甲氧基)-苯丙醛
• 英文名称: 3-(3-(benzyloxy)phenyl)propanal
• 英文别名: 3-(Phenylmethoxy)-benzenepropanal；3-(3-phenylmethoxyphenyl)propanal
• CAS: 75677-04-2
• 化学式: C₁₆H₁₆O₂
• 分子量: 240.302
• InChiKey: IPHLHNBJXAFUIE-UHFFFAOYSA-N

物化性质

• 沸点：
  373.8±22.0 °C(Predicted)
• 密度：
  1.088±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(苯基甲氧基)-苯丙醛 在 sodium chlorite 、 sodium dihydrogenphosphate dihydrate 、 palladium 10% on activated carbon 、 氢气 、 溶剂黄146 、 三氟乙酸 、 D-脯氨酸 作用下， 以 甲醇 、 二氯甲烷 、 水 、 乙腈 、 叔丁醇 为溶剂， 反应 46.5h， 生成 methyl (S)-2-amino-3-(3-hydroxyphenyl)propanoate
  参考文献：
  名称：

  Synthesis of the Southern Tripeptide (C₁–N₁₂) of Sanglifehrins Using Asymmetric Organocatalysis

  摘要：

  The tripeptide southern region of the novel cyclophilin binding natural product macrolides, namely sanglifehrins, is synthesized involving asymmetric organocatalysis as chirality-inducing step. List's asymmetric alpha-amination was used in the synthesis of the m-hydroxyphenylalanine part, whereas alpha-hydrazination was used for the piperazic ester part.

  DOI：

  10.1080/00397911.2014.947653
• 作为产物：
  描述：

  间-香豆酸 在 platinum(IV) oxide 硫酸 、 氢气 、 二异丁基氢化铝 、 potassium carbonate 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 51.5h， 生成 3-(苯基甲氧基)-苯丙醛
  参考文献：
  名称：

  Tandem reduction / intramolecular hydroxyalkylation of (3-hydroxyphenyl)alkanoates: a new regioselective approach to 1,8-dihydroxytetralins

  摘要：

  4-(3-hydroxyphenyl)-butanoates 4, on treatment with DIBALH, followed by hydrolytic work-up, undergo a novel completely regioselective intramolecular hydroxyalkylation reaction to give 1,8-dihydroxytetralins. The yield of the reaction depends heavily on the structure of starting material, best results being achieved with 3,3-disubstituted butanoates.

  DOI：

  10.1016/s0040-4039(00)74819-2

文献信息

• Synthesis and Biological Activity of New 3-Hydroxy-3-methylglutaryl-CoA Synthase Inhibitors: 2-Oxetanones with a meta-Substituent on the Benzene Ring in the Side Chain.
  作者：Hirokazu HASHIZUME、Hajime ITO、Naoaki KANAYA、Hajime NAGASHIMA、Hiroyuki USUI、Reiko OSHIMA、Munefumi KANAO、Hiroshi TOMODA、Toshiaki SUNAZUKA、Hidetoshi KUMAGAI、Satoshi OMURA

  DOI：10.1248/cpb.42.1272

  日期：——

  Isosteric side chain analogs of 3a were synthesized and tested for inhibitory activivies towards 3-hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) synthase and upon cholesterol production in Hep G2 cells and in mouse liver. It became clear that the lipophilic substituent on the aromatic ring and the terminal hydrophilic group in the side chain were important in the enhancement of activity. 4-[2-(3-n-Hexyloxyphanyl)ethyl]-3-hydroxymethyl-2-oxetanone (5a) showed equivalent inhibitory activity in vivo to that of 1233A.

  同位素侧链类似物3a被合成并测试了对3-羟基-3-甲基戊二酰辅酶A（HMG-CoA）合酶以及在Hep G2细胞和小鼠肝脏中胆固醇生成的抑制活性。结果表明，芳环上的亲脂性取代基和侧链末端的亲水性基团对活性的增强非常重要。4-[2-(3-正己氧基苯基)乙基]-3-羟甲基-2-氧杂环丁酮（5a）在体内的抑制活性与1233A相当。
• 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。
• Structure based optimization of chromen-based TNF-α converting enzyme (TACE) inhibitors on S1′ pocket and their quantitative structure–activity relationship (QSAR) study
  作者：Jee Sun Yang、Kwangwoo Chun、Jung Eun Park、Misun Cho、Jeongjea Seo、Doona Song、Hongchul Yoon、Chun-Ho Park、Bo-Young Joe、Jong-Hee Choi、Myung-Hwa Kim、Gyoonhee Han

  DOI：10.1016/j.bmc.2010.10.006

  日期：2010.12

  structure–activity relationship (QSAR) study using genetic function approximation technique (GFA) and docking study were performed to confirm the series of coumarin core TACE inhibitors. QSAR model have been evaluated internally and externally using test set prediction. Through docking study of each molecule, it is validated that the electrostatic descriptors from the QSAR equation could explain the importance

  根据对接研究，设计了一系列基于香豆素的TACE抑制剂以结合在TACE酶的S1'口袋中。合成了十二个类似物，大多数化合物具有体外TACE酶抑制作用以及细胞TNF-α抑制作用。其中15μl通过以30mg / kg的剂量口服有效抑制血清TNF-α的产生。化合物15l在角叉菜胶模型中也显示出42％的良好口服生物利用度，并有效抑制爪水肿。使用遗传功能近似技术（GFA）进行了定量构效关系（QSAR）研究和对接研究，以确认一系列香豆素核心TACE抑制剂。QSAR模型已使用测试集预测在内部和外部进行了评估。通过对每个分子的对接研究，证实了QSAR方程中的静电描述符可以很好地解释S1'口袋和TACE抑制活性的重要性。
• Mevalonolactone derivatives as inhibitors of 3-hydroxy-3-methylglutaryl coenzyme A reductase.
  作者：AIYA SATO、HIROSHI NOGUCHI、SEIJI MITSUI、ISAO KANEKO、YOKO SHIMADA

  DOI：10.1248/cpb.28.1509

  日期：——

  Mevalonolactone derivatives were prepared via stereo-and regioselective bromolactonization of γ, δ-unsaturated acids and their structure-activity relationship in connection with their inhibitory activity in vitro against 3-hydroxy-3-methylglutaryl coenzyme A (HMG CoA) reductase, a rate-limiting enzyme in cholesterol biosynthesis, was investigated.

  通过对γ, δ-不饱和酸进行立体选择性和区域选择性的溴内酯化反应制备了美瓦龙内酯衍生物，并研究了它们在体外对3-羟基-3-甲基谷氨酰辅酶A（HMG CoA）还原酶的抑制活性与其结构-活性关系，该酶是胆固醇生物合成中的限速酶。
• Catalytic Asymmetric Diarylation of Internal Acyclic Styrenes and Enamides
  作者：Yang Xi、Wenyi Huang、Chenchen Wang、Haojie Ding、Tingting Xia、Licheng Wu、Ke Fang、Jingping Qu、Yifeng Chen

  DOI：10.1021/jacs.2c03411

  日期：2022.5.11

  diastereo-, and stereoselective control of reactions with internal acyclic alkenes for the construction of functionalized acyclic alkanes still remain a persistent challenge. Here, we report a palladium-catalyzed asymmetric regiodivergent Heck-type diarylation of internal acyclic alkenes. The 1,2-diarylation of two accessible acyclic alkenes, cinnamyl carbamates and enamides with diazonium salts and aromatic

  烯烃的对映选择性转化是有机化合物不对称合成最重要的策略之一。化学-、非对映-和立体选择性控制与内部无环烯烃的反应以构建官能化无环烷烃仍然是一个持续的挑战。在这里，我们报告了内部无环烯烃的钯催化不对称区域发散 Heck 型二芳基化。使用重氮盐和芳族硼酸对两种可接近的无环烯烃、肉桂基氨基甲酸酯和烯酰胺进行 1,2-二芳基化反应，通过羰基配位辅助的瞬态钯环的立体定向形成提供含有邻位立体中心的产物。而且，烯酰胺的不对称迁移二芳基化能够通过中断的非对映选择性1,3-链行走过程形成不连续的立体中心。该协议简化了对嵌入关键生物活性基序中的高度功能化的多取代对映富集氨基甲酸酯和胺衍生物的访问。