1-(4-bromophenyl)hex-5-en-1-ol | 71434-58-7

• 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-bromophenyl)hex-5-en-1-ol
• 英文别名: 1-(4-Bromo-phenyl)-hex-5-en-1-ol
• CAS: 71434-58-7
• 化学式: C₁₂H₁₅BrO
• 分子量: 255.155
• InChiKey: RNJMSXMSWMJVPU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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-bromophenyl)hex-5-en-1-ol 在 Hoveyda-Grubbs catalyst second generation 、 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 phenyl (E)-7-(4-bromophenyl)-7-oxohept-2-enoate
  参考文献：
  名称：

  协同质子-电子转移介质在有利的应用偏压下进行电催化酮基-烯烃环化

  摘要：

  最近的研究表明，还原性协同质子-电子转移 (CPET) 是一种将净氢原子转移到有机基材上的强大策略；然而，CPET 在同源偶联之外的 C-C 键形成方面的直接应用尚未得到充分探索。我们在此报告了电催化 CPET ( e CPET)的扩展，其使用带有 Brønsted 碱基的钴茂介体 ([CpCoCp NMe 2 ][OTf]) 与酮烯烃底物，在通过e CPET 生成酮基自由基后进行环化。使用苯乙酮衍生的底物与束缚的丙烯酸酯作为自由基受体，在甲苯磺酸存在下，我们证明了通过表征顺式来实现烯酮-烯烃环化-内酯和烯烃产品。该 2 H + /2 e –过程的机理分析揭示了底物和酸的混合顺序以及具有适度负斜率的 Hammett 图，突出了连续 CPET 和 ET/PT 步骤对反应总速率和为初始 O-H 键的形成提供支持。通过受控电位电解在相对温和的还原电位下获得酮基自由基的能力使官能团在一系列底物上具有耐受性。

  DOI：

  10.1021/acs.inorgchem.2c00839
• 作为产物：
  描述：

  (±)-4-溴苯乙烯环氧化物 、 3-Butenylmagnesium bromide 在 lithium chloride 、 copper dichloride 作用下， 以 四氢呋喃 为溶剂， 以79%的产率得到1-(4-bromophenyl)hex-5-en-1-ol
  参考文献：
  名称：

  二取代吡咯烷的非对映选择性 C−H 键胺化

  摘要：

  我们在此报告了从脂肪族叠氮化物非对映选择性合成 2,5-二取代吡咯烷的改进方法。由二吡啶铁配合物 ( Ad L)FeCl(OEt 2 ) 介导的 C−H 胺化反应的实验和理论研究提供了非对映诱导模型，并允许对催化剂进行系统变化以提高选择性。在评估的铁醇盐和芳氧化物催化剂中，苯酚铁络合物在生成具有高非对映选择性的顺式2,5-二取代吡咯烷方面表现出优异的性能。

  DOI：

  10.1002/anie.201708519

文献信息

• Anti-Markovnikov Hydrofunctionalization of Alkenes: Use of a Benzyl Group as a Traceless Redox-Active Hydrogen Donor
  作者：Geoffroy Hervé Lonca、Derek Yiren Ong、Thi Mai Huong Tran、Ciputra Tejo、Shunsuke Chiba、Fabien Gagosz

  DOI：10.1002/anie.201705368

  日期：2017.9.11

  A protocol for the anti-Markovnikov hydrofunctionalization of alkenes has been developed by the use of a benzyl group as a traceless redox-active hydrogen donor. Under copper catalysis and in the presence of CF3- or N3-containing hypervalent iodine reagents, a series of homoallylic alcohol derivatives were hydrofunctionalized regioselectivity. A similar principle was also applied to the hydrofunctionalization

  通过使用苄基作为无痕的氧化还原活性氢供体，已经开发了用于烯烃的抗马尔可夫尼科夫加氢官能化的方案。在铜催化下并且在含有CF 3或N 3的高价碘试剂的存在下，一系列均烯丙基醇衍生物被加氢官能化区域选择性。类似的原理也应用于烯醇的加氢官能​​化。
• Copper-catalyzed remote oxidation of alcohols initiated by radical difluoroalkylation of alkenes: facile access to difluoroalkylated carbonyl compounds
  作者：Jian Zhang、Weiwei Jin、Cungui Cheng、Fang Luo

  DOI：10.1039/c8ob00889b

  日期：——

  A Cu-catalyzed oxidation of alcohols triggered by the radical difluoroalkylation of alkenes has been developed, providing facile access to a series of difluoroalkylated ketones or aldehydes in moderate to high yields. The concurrent realization of the catalytic oxidation of alcohols and difluoroalkylation of alkenes enables a highly efficient and attractive method for organic synthesis.

  已经开发了由烯烃的自由基二氟烷基化引发的Cu催化的醇氧化，可轻松以中等到高收率获得一系列二氟烷基化的酮或醛。醇的催化氧化和烯烃的二氟烷基化的同时实现实现了有机合成的高效且有吸引力的方法。
• Cyclopentane Formation from Flexible Precursors Using Samarium(II) Reagents
  作者：Christopher D. Aretz、Humberto Escobedo、Bryan J. Cowen

  DOI：10.1002/ejoc.201800102

  日期：2018.4.30

  This study presents three efficient methods for five‐membered ring carbocycle synthesis using samarium(II) reagents. Simple organic starting materials engage in intramolecular Reformatsky aldol, enolate alkylation, and pinacol cyclizations. A promising lead result has also been established demonstrating enantioselectivity in a chiral ligand controlled Reformatsky aldol reaction.

  这项研究提出了使用efficient（II）试剂合成五元环碳环的三种有效方法。简单的有机原料会参与分子内Reformatsky醇醛，烯醇烷基化和频哪醇环化反应。还建立了有希望的先导结果，证明了在手性配体控制的Reformatsky aldol反应中的对映选择性。
• 2',4'-DICHLORO-BIPHENYL-4-YL-HYDROXY-KETONES AND RELATED COMPOUNDS AND THEIR USE AS THERAPEUTIC AGENTS
  申请人：Greig Iain Robert

  公开号：US20080221220A1

  公开（公告）日：2008-09-11

  The present invention pertains generally to the field of therapeutic compounds, and more specifically to certain 2′,4′-dichloro-biphenyl-4-yl-hydroxy-ketones and related compounds (collectively referred to herein as “DCBP compounds”), and more particularly to compounds selected from compounds of the following formula and pharmaceutically acceptable salts, solvates, and hydrates thereof: wherein: n is independently 1, 2, 3, or 4; W is independently —C(═O)—, —CH(OH)—, or —C(═NOR OX )—; R OX is independently —H or C 1-3 alkyl; J is independently: —H, —R E1 , —C(═O)—R E2 , —C(═O)—O—R E3 , —C(═O)—O—S(═O) 2 OR E4 , —C(═O)—(CH 2 ) n —C(═O)OR E5 , —C(═O)—(CH 2 ) n —NR NE1 R NE2 , —C(═O)—(CH 2 ) n —NR NE3 —C(═O)R E6 , —C(═O)—(CH 2 ) n —C(═O)—NR NE4 R NE5 , or —P(═O)(OR E7 )(OR E8 ); wherein each of R E1 , R E2 , R E3 , R E4 , R E5 , R E6 , and R E7 is independently: —H, C 1-3 alkyl, -Ph, or —CH 2 -Ph. The present invention also pertains to pharmaceutical compositions comprising such compounds, and the use of such compounds and compositions, both in vitro and in vivo, in treatment and/or prevention, for example, of inflammation and/or joint destruction and/or bone loss; of disorders mediated by excessive and/or inappropriate and/or prolonged activation of the immune system; of, inflammatory and autoimmune disorders, for example, rheumatoid arthritis, psoriasis, psoriatic arthritis, inflammatory bowel disease, ankylosing spondylitis, and the like; of disorders associated with bone loss, such as bone loss associated with excessive osteoclast activation in rheumatoid arthritis, osteoporosis, cancer associated bone disease, Paget's disease and the like.

  本发明涉及治疗化合物领域，更具体地涉及某些2′，4′-二氯联苯基-4-羟基酮类化合物及相关化合物（以下统称为“DCBP化合物”），更进一步地，涉及选择自以下公式化合物及其药学上可接受的盐、溶剂和水合物的化合物：其中：n独立地为1、2、3或4；W独立地为—C(═O)—、—CH(OH)—或—C(═NOROX)—；ROX独立地为—H或C1-3烷基；J独立地为：—H、—RE1、—C(═O)—RE2、—C(═O)—O—RE3、—C(═O)—O—S(═O)2ORE4、—C(═O)—(CH2)n—C(═O)ORE5、—C(═O)—( )n—NRNE1RNE2、—C(═O)—( )n—NRNE3—C(═O)RE6、—C(═O)—( )n—C(═O)—NRNE4RNE5或—P(═O)(ORE7)(ORE8)；其中，RE1、RE2、RE3、RE4、RE5、RE6和RE7中的每一个独立地为：—H、C1-3烷基、-Ph或—CH2-Ph。本发明还涉及包含这样的化合物的制剂，以及这样的化合物和制剂的使用，无论是体外还是体内，在治疗和/或预防方面，例如：炎症和/或关节破坏和/或骨质丢失；由免疫系统过度和/或不适当和/或持续激活引起的疾病；炎症和自身免疫性疾病，例如：类风湿性关节炎、银屑病、银屑病性关节炎、炎症性肠病、强直性脊柱炎等；与骨质丢失有关的疾病，例如：类风湿性关节炎中过度破骨细胞激活引起的骨质丢失、骨质疏松症、与癌症相关的骨病、帕吉特病等。
• 2′,4′-dichloro-biphenyl-4-yl-hydroxy-ketones and related compounds and their use as therapeutic agents
  申请人：The University Court of the University of Aberdeen

  公开号：US07560597B2

  公开（公告）日：2009-07-14

  The present invention pertains generally to the field of therapeutic compounds, and more specifically to certain 2′,4′-dichloro-biphenyl-4-yl-hydroxy-ketones and related compounds (collectively referred to herein as “DCBP compounds”), and more particularly to compounds selected from compounds of the following formula and pharmaceutically acceptable salts, solvates, and hydrates thereof: wherein: n is independently 1, 2, 3, or 4; W is independently —C(═O)—, —CH(OH)—, or —C(═NOROX)—; ROX is independently —H or C1-3alkyl; J is independently: —H, —RE1, —C(═O)—RE2, —C(═O)—O—RE3, —C(═O)—O—S(═O)2ORE4, —C(═O)—(CH2)n—C(═O)ORE5, —C(═O)—(CH2)n—NRNE1RNE2, —C(═O)—(CH2)n—NRNE3—C(═O)RE6, —C(═O)—(CH2)n—C(═O)—NRNE4RNE5, or —P(═O)(ORE7)(ORE8); wherein each of RE1, RE2, RE3, RE4, RE5, RE6, and RE7 is independently: —H, C1-3alkyl, -Ph, or —CH2-Ph. The present invention also pertains to pharmaceutical compositions comprising such compounds, and the use of such compounds and compositions, both in vitro and in vivo, in treatment and/or prevention, for example, of inflammation and/or joint destruction and/or bone loss; of disorders mediated by excessive and/or inappropriate and/or prolonged activation of the immune system; of, inflammatory and autoimmune disorders, for example, rheumatoid arthritis, psoriasis, psoriatic arthritis, inflammatory bowel disease, ankylosing spondylitis, and the like; of disorders associated with bone loss, such as bone loss associated with excessive osteoclast activation in rheumatoid arthritis, osteoporosis, cancer associated bone disease, Paget's disease and the like.

  本发明通常涉及治疗化合物领域，更具体地涉及某些2′，4′-二氯联苯基-4-羟基酮和相关化合物（以下统称为“DCBP化合物”），更特别地涉及选择自以下公式化合物及其药学上可接受的盐、溶剂和水合物的化合物： 其中：n独立地为1、2、3或4；W独立地为—C（═O）—、—CH（OH）—或—C（═NOROX）—；ROX独立地为—H或C1-3烷基；J独立地为：—H、—RE1、—C（═O）—RE2、—C（═O）—O—RE3、—C（═O）—O—S（═O）2ORE4、—C（═O）—（CH2）n—C（═O）ORE5、—C（═O）—（ ）n—NRNE1RNE2、—C（═O）—（ ）n—NRNE3—C（═O）RE6、—C（═O）—（ ）n—C（═O）—NRNE4RNE5或—P（═O）（ORE7）（ORE8）；其中，RE1、RE2、RE3、RE4、RE5、RE6和RE7中的每一个独立地为：—H、C1-3烷基、-Ph或—CH2-Ph。本发明还涉及包含这样的化合物的制药组合物，以及这样的化合物和组合物在体内外的使用，例如，用于治疗和/或预防炎症和/或关节破坏和/或骨质流失；治疗由免疫系统过度和/或不适当和/或持续激活介导的疾病；治疗炎症和自身免疫性疾病，例如类风湿性关节炎、银屑病、银屑病性关节炎、炎症性肠病、强直性脊柱炎等；治疗与骨质流失相关的疾病，例如类风湿性关节炎中过度的骨吸收、骨质疏松症、癌症相关骨病、帕吉特病等。