5-methoxy-[1,1'-biphenyl]-2-carbaldehyde | 15144-84-0

• 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: 5-methoxy-[1,1'-biphenyl]-2-carbaldehyde
• 英文别名: 4-methoxy-2-phenylbenzaldehyde；5-methoxy-biphenyl-2-carbaldehyde；2-Formyl-5-methoxybiphenyl
• CAS: 15144-84-0
• 化学式: C₁₄H₁₂O₂
• 分子量: 212.248
• InChiKey: RSKDJEGUSMNMCI-UHFFFAOYSA-N

物化性质

• 沸点：
  374.9±30.0 °C(Predicted)
• 密度：
  1.114±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 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：

  5-methoxy-[1,1'-biphenyl]-2-carbaldehyde 在 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 生成 1-(5-methoxy[1,1′-biphenyl]-2-yl)ethan-1-one
  参考文献：
  名称：

  阴极材料决定联芳基酮肟化学C-H官能化的产物选择性

  摘要：

  多环N-杂芳族化合物及其相应的N-氧化物的合成是通过联芳基酮肟的电化学CH功能化开发的。当使用Pt阴极时，肟底物会经历脱氢环化反应，从而导致空前地获得各种N-杂芳族N-氧化物。通过顺序地阳极促进的脱氢环化作用和最初形成的N-氧化物中N-O键的阴极裂解，采用Pb阴极，将电合成的产物切换为脱氧的N-杂芳族化合物。

  DOI：

  10.1002/anie.201809679
• 作为产物：
  描述：

  5-methoxy-[1,1′-biphenyl]-2-carboxylic acid 生成 5-methoxy-[1,1'-biphenyl]-2-carbaldehyde
  参考文献：
  名称：

  合成2-（2-联苯基）乙胺作为潜在的止痛药。

  摘要：

  DOI：

  10.1021/jm00315a046

文献信息

• Lewis acid-catalyzed tandem synthesis of 9-sulfonylamino- and 9-arylfluorenes
  作者：Dayun Huang、Weiguang Yang、Jianlan Zhang、Xuesong Wang、Xinyan Wang、Yuefei Hu

  DOI：10.1039/c6ra03889a

  日期：——

  A Lewis acid-catalyzed three-step tandem synthesis of 9-arylfluorene was developed by simply heating a mixture of 2-formyl biphenyl, TsNCO and an arene. In the absence of arene, a two-step tandem synthesis of 9-sulfonylaminofluorene was achieved. These advances were mainly attributed to the discovery of an anhydrous synthesis of N-tosyl arylaldimines from TsNCO and arylaldehydes.

  通过简单地加热2-甲酰基联苯，TsNCO和芳烃的混合物，开发了路易斯酸催化的三步串联合成9-芳基芴的方法。在没有芳烃的情况下，实现了两步串联的9-磺酰基氨基芴的合成。这些进展主要归因于从TsNCO和芳基醛无水合成N-甲苯磺酰基芳基亚胺的发现。
• Synthesis of highly substituted fluorenones via metal-free TBHP-promoted oxidative cyclization of 2-(aminomethyl)biphenyls. Application to the total synthesis of nobilone
  作者：Ilya A P Jourjine、Lukas Zeisel、Jürgen Krauß、Franz Bracher

  DOI：10.3762/bjoc.17.181

  日期：——

  Highly substituted fluorenones are readily prepared in mostly fair to good yields via metal- and additive-free TBHP-promoted cross-dehydrogenative coupling (CDC) of readily accessible N-methyl-2-(aminomethyl)biphenyls and 2-(aminomethyl)biphenyls. This methodology is compatible with numerous functional groups (methoxy, cyano, nitro, chloro, and SEM and TBS-protective groups for phenols) and was further

  通过不含金属和添加剂的 TBHP 促进的易于获得的N-甲基-2-(氨甲基)联苯和 2-(氨甲基)联苯的交叉脱氢偶联 (CDC)，可以轻松制备高度取代的芴酮，收率基本上相当到良好。该方法与多种官能团（甲氧基、氰基、硝基、氯以及苯酚的 SEM 和 TBS 保护基团）兼容，并进一步用于天然产物诺比隆的首次全合成。
• Synthesis of Novel Structurally Simplified Estrogen Analogues with Electron-Donating Groups in Ring A
  作者：Lutz Tietze、Carsten Vock、Ilga Krimmelbein、Linda Nacke

  DOI：10.1055/s-0029-1216810

  日期：2009.6

  A library of 25 novel estrogen analogues were prepared in five to eight steps from mostly commercially available substituted anisoles via bromination, formylation, Corey-Fuchs reaction, elimination, and Sonogashira reaction.

  合成了一系列25种新型雌激素类似物，这些化合物通过五个至八个步骤，主要以市售的取代茴香醚为原料，经过溴化、甲醛化、Corey-Fuchs反应、消除反应及Sonogashira反应制备得到。
• Regio- and Chemoselective Kumada–Tamao–Corriu Reaction of Aryl Alkyl Ethers Catalyzed by Chromium Under Mild Conditions
  作者：Xuefeng Cong、Huarong Tang、Xiaoming Zeng

  DOI：10.1021/jacs.5b08621

  日期：2015.11.18

  the cross-coupling reactions with aryl ethers via C-O bond activation have attracted broad interest. However, the functionalizations of C-O bonds are mainly limited to nickel catalysis, and selectivity has long been a prominent challenge when several C-O bonds are present in the one molecule. We report here the first chromium-catalyzed selective cross-coupling reactions of aryl ethers with Grignard reagents

  作为一种环境友好的合成工具，通过 CO 键活化与芳基醚的交叉偶联反应引起了广泛的兴趣。然而，CO 键的功能化主要限于镍催化，当一个分子中存在多个 CO 键时，选择性一直是一个突出的挑战。我们在这里报告了第一个铬催化的芳基醚与格氏试剂通过 CO（烷基）键断裂的选择性交叉偶联反应。在室温下使用简单、廉价的铬 (II) 预催化剂结合亚氨基助剂实现了多种转化。它为高效和选择性地构建官能化芳香醛提供了新途径。
• COMPOUNDS OF PHOSPHINANES AND AZAPHOSPHINANES, A PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM
  申请人：LES LABORATOIRES SERVIER

  公开号：US20180016288A1

  公开（公告）日：2018-01-18

  Compounds of formula (I) wherein: Ak 1 represents an alkyl chain, X represents —(CH 2 ) m —, —CH(R)—, —N(R)—, —CH 2 —N(R)—, —N(R)—CH 2 — or —CH 2 —N(R)—CH 2 —, m and R are as defined in the description, R 1 and R 2 each represent H when X represents —(CH 2 ) m —, —CH(R)—, —N(R)—, —CH 2 —N(R)— or —N(R)—CH 2 —, or together form a bond when X represents —CH 2 —N(R)—CH 2 —, R 3 represents NH 2 , Cy-NH 2 , Cy-Ak 3 -NH 2 or piperidin-4-yl, Cy and Ak 3 are as defined in the description, R 4 and R 5 , which may be identical or different, each represent H or F, their optical isomers, and addition salts thereof with a pharmaceutically acceptable acid. Medicinal products containing the same which are useful in treating conditions requiring a TAFIa inhibitor.

  式(I)的化合物中： Ak1代表一个烷基链， X代表—(CH2)m—，—CH(R)—，—N(R)—，— —N(R)—，—N(R)— —或— —N(R)— —， m和R如描述中所定义， R1和R2分别在X代表—( )m—，—CH(R)—，—N(R)—，— —N(R)—或—N(R)— —时代表H， 或者当X代表— —N(R)— —时，它们一起形成一个键， R3代表NH2，Cy-NH2，Cy-Ak3-NH2或哌啶-4-基， Cy和Ak3如描述中所定义， R4和R5，可能相同也可能不同，每个代表H或F， 它们的光学异构体， 以及它们与药学上可接受的酸形成的盐。 包含这些化合物的药品，在治疗需要TAFIa抑制剂的情况下有用。