rac-1-(2-bromophenyl)hexane-1-ol | 749900-54-7

• 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: rac-1-(2-bromophenyl)hexane-1-ol
• 英文别名: 1-(2-Bromo-phenyl)-hexan-1-ol；1-(2-Bromophenyl)hexan-1-ol
• CAS: 749900-54-7
• 化学式: C₁₂H₁₇BrO
• 分子量: 257.17
• InChiKey: ARKOTRUWSJYGDH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  rac-1-(2-bromophenyl)hexane-1-ol 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 生成 1-(2'-bromophenyl)-hexan-1-one
  参考文献：
  名称：

  苯乙酮N-甲苯磺酰and与乙烯基的分子内反应：布朗斯台德酸促进阳离子环化成多取代茚

  摘要：

  在存在TsNHNH 2的情况下，开发了布朗斯台德酸促进的邻-（1-芳基乙烯基）苯乙酮衍生物的分子内环化反应，导致多取代的茚并酮具有复杂性和多样性，产率中等至优异。与自由基或卡宾涉及醛基N-甲苯磺酰hydr与乙烯基的环化形成鲜明对比，涉及阳离子环化途径，其中N-甲苯磺酰zone在该转化过程中用作亲电试剂和烷基化试剂。

  DOI：

  10.1039/d0cc07966a
• 作为产物：
  描述：

  1-(2'-bromophenyl)-hexan-1-one 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以90%的产率得到rac-1-(2-bromophenyl)hexane-1-ol
  参考文献：
  名称：

  Benzo lipoxin analogues

  摘要：

  提供苯唑啉类似物、其制备方法以及含有这些化合物的药物组合物。这些化合物和组合物在治疗各种疾病的方法中非常有用，包括炎症、自身免疫疾病和异常细胞增殖。

  公开号：

  US20050203184A1

文献信息

• Generation of Bromophenyllithium Reagents from Dibromobenzenes and Addition to Carbonyl and Nitrile Electrophiles
  作者：Stéphane Caron、Nga M. Do

  DOI：10.1055/s-2004-825611

  日期：——

  An evaluation of the mono-lithiation of all three regio-isomers of dibromobenzene using n-butylithium was performed. The resulting aryllithium reagents were added to electrophiles such as ketones, aldehydes, nitriles and amides to afford the desired ­benzylic alcohols or ketones.

  使用正丁基锂对二溴苯的三种区域异构体进行单锂化反应的评估已经完成。生成的芳基锂试剂与酮、醛、腈和酰胺等亲电试剂反应，得到所需苄醇或酮。
• Benzo Lipoxin Analogues
  申请人：PETASIS Nicos A.

  公开号：US20120142772A1

  公开（公告）日：2012-06-07

  Benzolipoxin analogs, methods of their preparation and pharmaceutical compositions containing the compounds are provided. The compounds and compositions are useful in methods for treatment of various diseases, including, inflammation, autoimmune disease and abnormal cell proliferation.

  本文提供苯唑环氧化物类似物的制备方法和含有该化合物的药物组合物。这些化合物和组合物在治疗各种疾病，包括炎症、自身免疫性疾病和异常细胞增殖的方法中有用。
• Palladium/Norbornene Cooperatively Catalyzed Modular Trifunctionalization of 2-Bromoaryl Ketone via a Decarbonylation Process
  作者：Qian Zhang、Yufeng Li、Xiaoliang Yang、Zeguo Fang、Dong Li

  DOI：10.1021/acs.orglett.4c01431

  日期：2024.7.12

  substrates and arylation reagents with a Heck acceptor. A decarbonylation process of the ketones also occurred in the reaction, finishing the modular ispo-Heck/ortho,ortho-diarylation in one pot. It provided the functionalized m-triphenyl derivatives with three new C–C bonds in moderate to excellent yields which exhibited good regioselectivities and functional group tolerance.

  钯/降冰片烯协同催化的 Catellani 型反应通常仅限于芳基碘化物作为底物。芳基溴的使用仍然具有挑战性。本文描述了 Pd/NBE 协同催化的 2-溴芳基酮的 Catellani 型反应。 2-溴芳基酮用作底物和具有 Heck 受体的芳基化试剂。反应中还发生酮的脱羰过程，一锅完成模块化ispo -Heck/邻、邻二芳基化反应。它以中等至优异的产率提供了具有三个新 C-C 键的官能化间三苯衍生物，表现出良好的区域选择性和官能团耐受性。
• Design and synthesis of benzo-lipoxin A4 analogs with enhanced stability and potent anti-inflammatory properties
  作者：Nicos A. Petasis、Raquel Keledjian、Yee-Ping Sun、Kalyan C. Nagulapalli、Eric Tjonahen、Rong Yang、Charles N. Serhan

  DOI：10.1016/j.bmcl.2008.01.013

  日期：2008.2

  A new class of chemically and metabolically stable lipoxin analogs featuring a replacement of the tetraene unit of native LXA(4) with a substituted benzo-fused ring system have been designed and studied. These molecules were readily synthesized via a convergent synthetic route involving iterative palladium-mediated cross-coupling, and exhibit enhanced chemical stability, as well as resistance to metabolic inactivation via eicosanoid oxido-reductase. These new LX analogs were evaluated in a model of acute inflammation and were shown to exhibit potent anti-inflammatory properties, significantly decreasing neutrophil infiltration in vivo. The most potent among these was compound 9 (o-[9,12]-benzo-15-epi-LXA(4) methyl ester. Taken together, these findings help identify a new class of stable and easily prepared LX analogs that may serve as novel tools and as promising leads for new anti-inflammatory agents with improved therapeutic pro. le. (c) 2008 Elsevier Ltd. All rights reserved.
• Synthesis of Bifunctional Lipoxin‐Derived Enzyme‐Triggered CO‐Releasing Molecules (LipET‐CORMs)
  作者：Lars Hemmersbach、Ruth Adam、Christina Plevnali、Xinmiao Zhang、Benito Yard、Hans‐Günther Schmalz

  DOI：10.1002/ejoc.202201424

  日期：2023.3

  AbstractIn an attempt to develop new anti‐inflammatory agents which act by co‐release of carbon monoxide (CO) and a specialized pro‐resolving mediator, we designed conjugates of a lipoxin A4 analogue and an acyloxycyclohexadiene‐Fe(CO)3 complex as an esterase‐triggered CO‐releasing molecule (ET‐CORM). After adjustment of the protecting group strategy, two of such compounds were successfully prepared by total synthesis (12 steps; 4–5 % overall yield) starting from deoxy‐d‐ribose and exploiting a Wittig olefination and an intermolecular Heck reaction as key C−C bond‐forming steps. A crucial late reduction of an aryl‐ketone moiety in the presence of a highly sensitive dienol ester functionality was achieved with BH3‐SMe2 in the presence of catalytic amounts of NaBH4. Both target compounds were dose‐dependently toxic towards cultured human umbilical vein endothelial cells (HUVEC), with LipET‐CORM 1‐A being slightly more toxic. While induction of heme oxygenase 1 (HO‐1) in HUVEC was observed for both compounds, they did not inhibit TNF‐α‐mediated VCAM‐1 expression in these cells. In M2 polarized macrophages HO‐1 expression was more pronounced as compared to M1 polarized macrophages. In both types of macrophages HO‐1 expression was downregulated by lipopolysaccharide, but only in M2 macrophages HO‐1 expression was rescued by LipET‐CORM. 15‐Lipoxygenase (15‐LO) was only expressed in M2 macrophages and was not influenced by LipET‐CORM. Collectively our data demonstrate that LipET‐CORMs induce HO‐1 expression in endothelial cells and M2 polarized macrophages. The role of the intra‐cellular released lipoxin A4 in resolution of inflammation, however, remains to be assessed.