1-(4-biphenylyl)-n-pentanol | 50673-89-7

• 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: 1-(4-biphenylyl)-n-pentanol
• 英文别名: 1-biphenyl-4-yl-pentan-1-ol；1-([1,1'-biphenyl]-4-yl)pentan-1-ol；1-(4-Biphenyl)-pentanol；1-(4-Biphenylyl)pentanol；1-(4-phenylphenyl)pentan-1-ol
• CAS: 50673-89-7
• 化学式: C₁₇H₂₀O
• mdl: MFCD16357168
• 分子量: 240.345
• InChiKey: QLIGCPRAHIGSPJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.294
• 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：

  1-(4-biphenylyl)-n-pentanol 在 吡啶 、 manganese(IV) oxide 、 碘 作用下， 以 二氯甲烷 为溶剂， 反应 62.0h， 生成 (E)-2-(2-chlorophenyl)-N-[4-(4-phenylphenyl)-5-propyl-1,3-thiazol-2-yl]ethenesulfonamide
  参考文献：
  名称：

  Sulfonylated aminothiazoles as new small molecule inhibitors of protein phosphatases

  摘要：

  Based on a previously identified lead structure, SC-alpha alpha delta9, we have developed a versatile new chemical scaffold that can be readily modified to generate libraries of both Tyr and dual specificity phosphatase inhibitors with reduced molecular weight and lipophilicity. The most potent analogue identified to dare, aminothiazole 8z, inhibits the dual specificity phosphatase Cdc25B with a K-i of 4.6 +/- 0.4 muM and a Hill coefficient of 2. (C) 2001 Elsevier Science Ltd. Ail rights reserved.

  DOI：

  10.1016/s0960-894x(00)00658-2
• 作为产物：
  描述：

  正溴丁烷 、 对苯基苯甲醛 生成 1-(4-biphenylyl)-n-pentanol
  参考文献：
  名称：

  降胆固醇药。二。芳基烷基氢琥珀酸酯和戊二酸酯对-羟基-甲基戊二酰辅酶A还原酶的抑制作用。

  摘要：

  DOI：

  10.1002/jps.2600620620

文献信息

• Direct Transformation of Aryl 2-Pyridyl Esters to Secondary Benzylic Alcohols by Nickel Relay Catalysis
  作者：Xianqing Wu、Xiaobin Li、Wenyi Huang、Yun Wang、Hui Xu、Liangzhen Cai、Jingping Qu、Yifeng Chen

  DOI：10.1021/acs.orglett.9b00774

  日期：2019.4.5

  secondary benzylic alcohols via tandem Ni-catalyzed cross-coupling reactions of aromatic 2-pyridyl esters with alkyl zinc reagents and carbonyl group reduction by Ni–H species is achieved. Preliminary mechanistic studies reveal that the Ni–H species is generated in situ via β-hydride elimination of the Negishi reagents. The reaction is catalyzed by bench-stable nickel salts under mild conditions with

  通过芳族2-吡啶酯与烷基锌试剂的串联Ni催化的交叉偶联反应，以及Ni-H物种还原的羰基，可以将芳基酯直接转化为仲苄醇。初步的机理研究表明，Ni-H物种是通过Negishi试剂的β-氢化物消除原位生成的。在温和的条件下，具有稳定的官能团耐受性，可通过稳定的镍盐催化该反应。
• Rhodium-Catalyzed Deoxygenation and Borylation of Ketones: A Combined Experimental and Theoretical Investigation
  作者：Lei Tao、Xueying Guo、Jie Li、Ruoling Li、Zhenyang Lin、Wanxiang Zhao

  DOI：10.1021/jacs.0c07854

  日期：2020.10.21

  The rhodium-catalyzed deoxygenation and borylation of ketones with B2pin2 have been developed, leading to efficient formation of alkenes, vinylboronates, and vinyldiboronates. These reactions feature mild reaction conditions, a broad substrate scope, and excellent functional-group compatibility. Mechanistic studies support that the ketones initially undergo a Rh-catalyzed deoxygenation to give alkenes

  已经开发了铑催化的酮与 B2pin2 的脱氧和硼酸化，从而有效地形成烯烃、乙烯基硼酸酯和乙烯基二硼酸酯。这些反应的特点是反应条件温和，底物范围广，官能团兼容性好。机理研究支持酮最初经过 Rh 催化脱氧以通过硼烯醇化物中间体得到烯烃，随后 Rh 催化的烯烃脱氢硼化导致乙烯基硼酸酯和二硼化产物的形成，这也得到 DFT 计算的支持。
• Synthesis, biological evaluation, and molecular modeling studies of methylene imidazole substituted biaryls as inhibitors of human 17α-hydroxylase-17,20-lyase (CYP17)—Part II: Core rigidification and influence of substituents at the methylene bridge
  作者：Qingzhong Hu、Matthias Negri、Kerstin Jahn-Hoffmann、Yan Zhuang、Sureyya Olgen、Marc Bartels、Ursula Müller-Vieira、Thomas Lauterbach、Rolf W. Hartmann

  DOI：10.1016/j.bmc.2008.07.011

  日期：2008.8

  Thirty-five novel substituted imidazolyl methylene biphenyls have been synthesized as CYP17 inhibitors for the potential treatment of prostate cancer. Their activities have been tested with recombinant human CYP17 expressed in Escherichia coli. Promising compounds were tested for selectivity against CYP11B1, CYP11B2, and hepatic CYP enzymes 3A4, 1A2, 2B6 and 2D6. The core rigidified compounds (30-35)

  已合成了35种新型取代的咪唑基亚甲基联苯作为CYP17抑制剂，可用于治疗前列腺癌。已经用在大肠杆菌中表达的重组人CYP17测试了它们的活性。测试了有前途的化合物对CYP11B1，CYP11B2和肝CYP酶3A4、1A2、2B6和2D6的选择性。核心刚性化合物（30-35）是最活跃的化合物，比酮康唑更有效，并达到阿比特龙的活性。但是，它们不是非常有选择性。在大鼠中进一步检查了血浆中睾丸激素水平和药代动力学特性的另一种更有效且更具选择性的抑制剂（化合物23，IC（50）= 345 nM）。相较于参考文献Abiraterone，体内有23种活性更高，显示更长的血浆半衰期（10小时）和更高的生物利用度。使用我们的CYP17同源蛋白模型，与选定化合物进行对接研究，以研究抑制剂与活性位点氨基酸残基之间的可能相互作用。
• Scalable Aerobic Oxidation of Alcohols Using Catalytic DDQ/HNO₃
  作者：Tania Katsina、Louis Clavier、Jean-François Giffard、Nayane Macedo Portela da Silva、Jean Fournier、Rodolphe Tamion、Chloé Copin、Stellios Arseniyadis、Alexandre Jean

  DOI：10.1021/acs.oprd.9b00513

  日期：2020.5.15

  A selective, practical, and scalable aerobic oxidation of alcohols is described that uses catalytic amounts of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) and HNO3, with molecular oxygen serving as the terminal oxidant. The method was successfully applied to the oxidation of a wide range of benzylic, propargylic, and allylic alcohols, including two natural products, namely, carveol and podophyllotoxin

  描述了一种选择性，实用且可扩展的酒精好氧氧化方法，该方法使用催化量的2,3-二氯-5,6-二氰基-1,4-苯醌（DDQ）和HNO 3，分子氧作为末端氧化剂。该方法已成功应用于多种苄醇，炔丙基醇和烯丙基醇的氧化，包括两种天然产物，即香芹酚和鬼臼毒素。该条件也适用于对甲氧基苄基醚的选择性氧化脱保护。
• Hypocholesterolemic agents III: Inhibition of β‐hydroxy‐β‐methylglutaryl coenzyme a reductase by half acid esters of 1‐(4‐biphenylyl)pentanol
  作者：Kenneth E. Guyer、Sharon G. Boots、Paul E. Marecki、Marvin R. Boots

  DOI：10.1002/jps.2600650417

  日期：1976.4

  A series of half acid esters of 1-(4-biphenylyl)pentanol was synthesized and assayed for inhibition of rat liver beta-hydroxy-beta-methylglutaryl coenzyme A reductase. The number of methylenes separating the carboxyl and ester groups was varied from zero to six. A minimum of one methylene was required for reasonable activity. Further separation of the carboxyl and ester groups produced small changes

  合成了一系列1-（4-联苯基）戊醇的半酸酯，并测定了对大鼠肝脏β-羟基-β-甲基戊二酰辅酶A还原酶的抑制作用。分离羧基和酯基的亚甲基的数量从零到六不等。为了合理的活性，最少需要一种亚甲基。羧基和酯基的进一步分离产生小的活性变化。对几种异构（顺式和反式）半酸酯的研究表明，活性与构型无关。通过掺入3-羟基对戊二酸类似物的酸部分进行的修饰使活性增加了六倍。