(4-甲基联苯-3-基)-甲醇 | 89951-79-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (4-甲基联苯-3-基)-甲醇
• 中文别名: (4'-甲基 - [1,1'-联苯] -3-基)甲醇
• 英文名称: (4'-methylbiphenyl-3-yl)methanol
• 英文别名: (4’-methyl-[1,1‘-biphenyl]-3-yl)methanol；(4'-Methyl-[1,1'-biphenyl]-3-yl)methanol；[3-(4-methylphenyl)phenyl]methanol
• CAS: 89951-79-1
• 化学式: C₁₄H₁₄O
• mdl: MFCD05981708
• 分子量: 198.265
• InChiKey: UPANSIDQWGNVBX-UHFFFAOYSA-N

物化性质

• 沸点：
  346.3±11.0 °C(Predicted)
• 密度：
  1.072±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-(6-(aminomethyl)-1-oxoisoindolin-2-yl)piperidine-2,6-dione hydrochloride 、 (4-甲基联苯-3-基)-甲醇 、 N,N'-羰基二咪唑 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以40 %的产率得到(4’-methyl[1,1‘-biphenyl]-3-yl)methyl ((2-(2,6-dioxopiperidin-3-yl)-3-oxoisoindolin-5-yl)methyl)carbamate
  参考文献：
  名称：

  WO2023/69700

  摘要：

  公开号：
• 作为产物：
  描述：

  在 吡啶 、 4-二甲氨基吡啶 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 36.0h， 生成 (4-甲基联苯-3-基)-甲醇
  参考文献：
  名称：

  Pd-Mediated C-C and C-S Bond Formation on Solid Support: A Scope and Limitations Study

  摘要：

  本文报道了零价钯催化的芳基卤代物与聚苯乙烯树脂相连的配体、硼酸衍生物（铃木偶联反应）、芳基和乙烯基锡化合物（斯蒂尔偶联反应）以及硫醇之间的偶联反应的范围和局限性。针对所有反应，经过优化条件并使用不同试剂进行评估。在许多情况下，从固相载体上切割下来的产物收率极佳。大多数情况下，经过优化的反应条件优于先前文献报道的条件。

  DOI：

  10.1055/s-1998-22661

文献信息

• Studies on Pd/NiFe₂O₄ catalyzed ligand-free Suzuki reaction in aqueous phase: synthesis of biaryls, terphenyls and polyaryls
  作者：Sanjay R Borhade、Suresh Babsaheb Waghmode

  DOI：10.3762/bjoc.7.41

  日期：——

  Palladium supported on nickel ferrite (Pd/NiF₂O₄) was found to be a highly active catalyst for the Suzuki coupling reaction between various aryl halides and arylboronic acids. The reaction gave excellent yields (70–98%) under ligand free conditions in a 1:1 DMF/H₂O solvent mixture, in short reaction times (10–60 min). The catalyst could be recovered easily by applying an external magnetic field. The polyaryls were similarly synthesized.

  钯负载在镍铁氧体（Pd/NiF₂O₄）被发现是一种对各种芳基卤化物和芳基硼酸的铃木偶联反应具有高活性的催化剂。在无需配体、1:1的DMF/H₂O溶剂混合物中，反应在短时间（10-60分钟）内给出了极好的产率（70-98%）。通过施加外部磁场，可以轻松回收催化剂。聚芳基化合物也以类似方式合成。
• A General Suzuki–Miyaura Coupling of Aryl Chlorides with Potassium Aryltrifluoroborates­ in Water Catalyzed by an Efficient CPCy Phendole-phos–Palladium Complex
  作者：Chau So、Fuk Kwong、On Yuen、Shun Wong、Kin Chan

  DOI：10.1055/s-0033-1338660

  日期：——

  General examples of the palladium-catalyzed Suzuki–Miyaura cross-coupling of aryl or heteroaryl chlorides with potassium aryl- or heteroaryltrifluoroborates in water are presented. The palladium complex comprising of palladium(II) acetate and ‘CPCy Phendole-phos’ is found to be a highly effective catalyst system for this coupling reaction with low catalyst loading (down to 0.005 mol% Pd). General examples

  摘要 给出了水中钯催化的芳基或杂芳基氯化物与芳基或杂芳基三氟硼酸钾的Suzuki-Miyaura交叉偶联的一般实例。发现由乙酸钯（II）和“ CPCy Phendole-phos”组成的钯络合物是用于该偶联反应且催化剂负载量低（低至0.005mol％Pd）的高效催化剂体系。 给出了水中钯催化的芳基或杂芳基氯化物与芳基或杂芳基三氟硼酸钾的Suzuki-Miyaura交叉偶联的一般实例。发现由乙酸钯（II）和“ CPCy Phendole-phos”组成的钯络合物是用于该偶联反应且催化剂负载量低（低至0.005mol％Pd）的高效催化剂体系。
• Development of Unimolecular Tetrakis(piperidin-4-ol) as a Ligand for Suzuki-Miyaura Cross-Coupling Reactions: Synthesis of Incrustoporin and Preclamol
  作者：Jothi L. Nallasivam、Rodney A. Fernandes

  DOI：10.1002/ejoc.201500353

  日期：2015.6

  cross-coupling reactions under aerobic conditions. Various biaryls, terphenyls, and heterocyclic biphenyls were obtained in good to excellent yields. The ligands were also capable of catalyzing the Heck–Mizoroki reaction. As an application, the Suzuki–Miyaura coupling reaction was used in the synthesis of incrustoporin, its analogs, and the drug molecule preclamol.

  多米诺 aza-Cope/aza-Prins 级联反应合成了一类新的 4-羟基哌啶附加单分子、双、三和四单分子化合物，作为有效配体在有氧条件下催化 Suzuki-Miyaura 交叉偶联反应. 以良好到极好的收率获得了各种联芳基、三联苯和杂环联苯。配体还能够催化 Heck-Mizoroki 反应。作为应用，Suzuki-Miyaura 偶联反应用于合成肠壳孔蛋白、其类似物和药物分子 preclamol。
• Pd-catalyzed atom-efficient cross-coupling of triarylbismuth reagents with protecting group-free iodophenylmethanols: Synthesis of biarylmethanols
  作者：Maddali L.N. Rao、Suresh Meka

  DOI：10.1016/j.tetlet.2020.151676

  日期：2020.3

  An atom-efficient procedure for the synthesis of functionalized biarylmethanols via the Pd-catalyzed cross-coupling reactions of differently functionalized iodophenylmethanols and triarylbismuth reagents is described. This protecting group-free direct couplings of 2-, 3- or 4-iodophenylmethanols with triarylbismuth reagents afforded biarylmethanols in good to high yields.

  描述了通过不同功能化的碘代苯基甲醇与三芳基铋试剂的钯催化交叉偶联反应合成功能化联芳基甲醇的原子有效程序。这种2-，3-或4-碘苯基甲醇与三芳基铋试剂的无保护基团的直接偶联以良好或高收率提供了联芳基甲醇。
• Biphenyl Derivatives and Their Use in Treating Hepatitis C
  申请人：Wheelhouse Christopher James

  公开号：US20080255105A1

  公开（公告）日：2008-10-16

  A compound which is a biphenyl derivative of formula (I), or a pharmaceutically acceptable salt thereof wherein: R 1 is a C 1 -C 6 alkyl group or a moiety -A 1 , -L 1 -A 1 , -A 1 -A 1 ′, -L 1 -A 1 -A 1 ′, -A 1 -L 1 -A 1 ′, -A 1 -Y 1 -A 1 ′, -A 1 -Het 1 -A 1 ′, -L 1 -A 1 -Y 1 -A 1 ′, -L 1 -A 1 -Het 1 -A 1 ′, -L 1 -Het 1 -A 1 , -L 1 -Y 1 -A 1 , -L 1 -Y 1 -Het 1 -A 1 , -L 1 -Het 1 -Y 1 -A 1 , -L 1 -Y 1 -Het 1 -L 1 ′, -A 1 -Y 1 -Het 1 -A 1 ′, -A 1 -Het 1 -Y 1 -A 1 ′, -A 1 -Het 1 -L 1 -A 1 ′, -A 1 -L 1 -Het 1 -A 1 ′ or -L 1 -Het 1 -L 1 ′; -A and B are the same or different and each represent a direct bond or a —CO—NR′—, —NR′—CO—, —NR′—CO 2 —, —CO—, —NR′—CO—NR″—, —NR′—S(O) 2 —, —S(O) 2 —NR′—, —SO 2 —, —NR′—, —NR′—CO—CO—, —CO—O—, —O—CO—, —(C 1 -C 2 alkylene)-NR′— or —(C 1 -C 2 hydroxyalkylene)-NR′-moiety, wherein R′ and R″ are the same or different and each represent hydrogen or C 1 -C 4 alkyl; —R 2 and R 3 are the same or different and each represent C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy or halogen; n and m are the same or different and each represent 0 or 1; R 4 is a C 1 -C 6 alkyl group or a moiety -A 4 , -L 4 -A 4 , -A 4 -A 4 ′, -L 4 -A 4 -A 4 ′, -A 4 -L 4 -A 4 ′, -A 4 -Y 4 -A 4 ′, -A 4 -Het 4 -A 4 ′, -L 4 -A 4 -Y 4 -A 4 ′, -L 4 -A 4 -Het 4 -A 4 ′, -L 4 -Het 4 -A 4 , -L 4 -Y 4 -A 4 , -L 4 -Y 4 -Het 4 -A 4 , -L 4 -Het 4 -Y 4 -A 4 , -L 4 -Y 4 -Het 4 -L 4 ′, -A 4 -Y 4 -Het 4 -A 4 ′, -A 4 -Het 4 -Y 4 -A 4 ′, -A 4 -Het 4 -L 4 -A 4 ′, -A 4 -L 4 -Het 4 -A 4 ′ or -L 4 -Het 4 -L 4 ′, each A 1 , A 4 , A 1 ′ and A 4 ′ are the same or different and represent a phenyl, 5- to 10-membered heteroaryl, 5- to 10-membered heterocyclyl or C 3 -C 8 carbocyclyl moiety; each L 1 and L 4 is the same or different and represents a C 1 -C 4 alkylene or a C 1 -C 4 hydroxyalkylene group; each Y 1 and Y 4 is the same or different and represents —CO—, —SO— or —S(O) 2 —; each L 1 ′ and L 4 ′ is the same or different and represents hydrogen or a C 1 -C 4 alkyl group; and each Het 1 and Het 4 is the same or different and represents —O—, —S— or —NR′—, wherein R′ is hydrogen or a C 1 -C 4 alkyl group, the phenyl, heteroaryl, heterocyclyl and carbocyclyl moieties in R 1 and R 4 being optionally fused to a phenyl, 5- to 10-membered heteroaryl or 5- to 10-membered heterocyclyl ring; and the phenyl, heteroaryl, heterocyclyl and carbocyclyl moieties in R 1 and R 4 being unsubstituted or substituted by (a) a single unsubstituted substituent selected from —(C 1 -C 4 alkyl)-X 1 , —CO 2 R′, —SO 2 NR′R″, —S(O) 2 —R′, —CONR′R″, —NR′—CO—R′″, —NR′—S(O) 2 —R′″, —CO—NR′—(C 1 -C 4 alkyl)-NR′R″ and —CO—O—(C 1 -C 4 alkyl)-NR′R″ and/or (b) 1, 2 or 3 unsubstituted substituents selected from —(C 1 -C 4 alkyl)-X 2 , halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy, C 1 -C 4 hydroxyalkyl, hydroxy, cyano, nitro and —NR′R″, wherein X 1 is —CO 2 R′, —SO 2 —R′, —NR′—CO 2 —R″, —NR′—S(O) 2 —R′″, —CONR′R″ or —SO 2 —NR′R″, each X 2 is the same or different and is cyano, nitro or —NR′R″, each R′ and R″ is the same or different and represents hydrogen or C 1 -C 4 alkyl and each R′″ is the same or different and represents C 1 -C 4 alkyl.

  化合物是公式（I）的二苯基衍生物，或其药学上可接受的盐，其中：R1是C1-C6烷基或基-A1，-L1-A1，-A1-A1'，-L1-A1-A1'，-A1-L1-A1'，-A1-Y1-A1'，-A1-Het1-A1'，-L1-A1-Y1-A1'，-L1-A1-Het1-A1'，-L1-Het1-A1，-L1-Y1-A1，-L1-Y1-Het1-A1，-L1-Het1-Y1-A1，-L1-Y1-Het1-L1'，-A1-Y1-Het1-A1'，-A1-Het1-Y1-A1'，-A1-Het1-L1-A1'，-A1-L1-Het1-A1'或-L1-Het1-L1'的基团；A和B相同或不同，每个代表直接键或-CO-NR'，-NR'-CO，-NR'-CO2，-CO，-NR'-CO-NR"，-NR'-S（O）2，-S（O）2-NR'，-SO2，-NR'，-NR'-CO-CO-，-CO-O-，-O-CO-，-（C1-C2烷基）-NR'或-（C1-C2羟基烷基）-NR'基团，其中R'和R"相同或不同，每个代表氢或C1-C4烷基；-R2和R3相同或不同，每个代表C1-C4烷基，C1-C4烷氧基，C1-C4卤代烷基，C1-C4卤代烷氧基或卤素；n和m相同或不同，每个代表0或1；R4是C1-C6烷基或基-A4，-L4-A4，-A4-A4'，-L4-A4-A4'，-A4-L4-A4'，-A4-Y4-A4'，-A4-Het4-A4'，-L4-A4-Y4-A4'，-L4-A4-Het4-A4'，-L4-Het4-A4，-L4-Y4-A4，-L4-Y4-Het4-A4，-L4-Het4-Y4-A4，-L4-Y4-Het4-L4'，-A4-Y4-Het4-A4'，-A4-Het4-Y4-A4'，-A4-Het4-L4-A4'，-A4-L4-Het4-A4'或-L4-Het4-L4'，每个A1，A4，A1'和A4'相同或不同，代表苯基，5-至10-成员杂芳基，5-至10-成员杂环基或C3-C8碳环基基团；每个L1和L4相同或不同，代表C1-C4烷基或C1-C4羟基烷基基团；每个Y1和Y4相同或不同，代表-CO-，-SO-或-S（O）2-；每个L1'和L4'相同或不同，代表氢或C1-C4烷基基团；每个Het1和Het4相同或不同，代表-O-，-S-或-NR'-，其中R'是氢或C1-C4烷基，R1和R4中的苯基，杂芳基，杂环基和碳环基基团可以选择地与苯基，5-至10-成员杂芳基或5-至10-成员杂环基环融合；R1和R4中的苯基，杂芳基，杂环基和碳环基基团可以未经取代或经过（a）单个未取代的取代基的取代，所选的取代基为-（C1-C4烷基）-X1，-CO2R'，-SO2NR'R"，-S（O）2-R'，-CONR'R"，-NR'-CO-R'"，-NR'-S（O）2-R'"，-CO-NR'（C1-C4烷基）-NR'R"和-CO-O-（C1-C4烷基）-NR'R"和/或（b）1,2或3个未取代的取代基，所选的取代基为-（C1-C4烷基）-X2，卤素，C1-C4烷基，C1-C4烷氧基，C1-C4卤代烷基，C1-C4卤代烷氧基，C1-C4羟基烷基，羟基，氰基，硝基和-NR'R"，其中X1为-CO2R'，-SO2-R'，-NR'-CO2-R"，-NR'-S（O）2-R'"，-CONR'R"或-SO2-NR'R"，每个X2相同或不同，为氰基，硝基或-NR'R"，每个R'和R"相同或不同，代表氢或C1-C4烷基，每个R'"相同或不同，代表C1-C4烷基。