6-bromo-2-hexen-1-ol | 71032-11-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-bromo-2-hexen-1-ol
• 英文别名: 6-bromohex-2-en-1-ol；6-Bromhexen-2-ol；6-Bromohex-2-en-1-ol
• CAS: 71032-11-6
• 化学式: C₆H₁₁BrO
• 分子量: 179.057
• InChiKey: LCAJAAKSZFJUEA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  8
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  6-bromo-2-hexen-1-ol 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 L-(+)-酒石酸二乙酯 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 六甲基磷酰三胺 、 pyridine-SO3 complex 、 双氧水 、 sodium hexamethyldisilazane 、 二甲基亚砜 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 0.17h， 生成 (2E,6S,8S,9E,12S)-16,18-bis(ethoxymethoxy)-12-methyl-7,13-dioxatricyclo[13.4.0.06,8]nonadeca-1(15),2,9,16,18-pentaen-14-one
  参考文献：
  名称：

  抑制激酶的支架aigialomycin D的模块化不对称合成。

  摘要：

  DOI：

  10.1002/anie.200600593
• 作为产物：
  描述：

  ethyl 6-bromohex-2-enoate 在 二异丁基氢化铝 作用下， 以 正己烷 为溶剂， 生成 6-bromo-2-hexen-1-ol
  参考文献：
  名称：

  Conformational effects on the 2,3-sigmatropic shift of sulfur-stabilized ylides and enolates involving bicyclic transition states

  摘要：

  DOI：

  10.1021/jo01332a029

文献信息

• Allylic Aminations with Hindered Secondary Amine Nucleophiles Catalyzed by Heterobimetallic Pd–Ti Complexes
  作者：Whitney K. Walker、Diana L. Anderson、Ryjul W. Stokes、Stacey J. Smith、David J. Michaelis

  DOI：10.1021/acs.orglett.5b00058

  日期：2015.2.6

  palladium–titanium complexes are highly effective catalysts for allylic aminations of allylic chlorides with hindered secondary amine nucleophiles. Three titanium-containing ligands are shown to assemble active catalysts in situ and enable catalysis at room temperature. A variety of sterically bulky secondary amines are efficiently allylated in high yields with as little as 1 mol % palladium catalyst. Piperidine and

  膦酰胺骨架的异双金属钯-钛络合物是高效的催化剂，用于烯丙基氯化物与受阻仲胺亲核试剂的烯丙基胺化反应。示出了三种含钛的配体在原位组装活性催化剂并能够在室温下催化。使用低至1 mol％的钯催化剂，可以高收率高效地烯丙基化各种空间庞大的仲胺。哌啶和吡咯烷产物也可通过受阻胺亲核试剂的分子内胺化而有效产生。
• Ir(I)-Catalyzed Enantioselective Decarboxylative Allylic Etherification: A General Method for the Asymmetric Synthesis of Aryl Allyl Ethers
  作者：Dongeun Kim、Srinivasa Reddy、Om V. Singh、Jae Seung Lee、Suk Bin Kong、Hyunsoo Han

  DOI：10.1021/ol3033237

  日期：2013.2.1

  Ir(I)-catalyzed enantioselective decarboxylative allylic etherification of aryl allyl carbonates provides aryl allyl ethers. Key to the generality and high stereoselection of the reaction is the use of the intramolecular decarboxylative allylation process and [Ir(dbcot)Cl]2 as an Ir(I) source. Ir(I)-catalyzed diastereoselective decarboxylative allylic etherification, combined with asymmetric aldehyde

  Ir（I）催化的芳基碳酸烯丙酯的对映选择性脱羧烯丙基醚化反应提供了芳基烯丙基醚。反应的一般性和高立体选择的关键是使用分子内脱羧烯丙基化过程和[Ir（dbcot）Cl] 2作为Ir（I）来源。Ir（I）催化的非对映选择性脱羧烯丙基醚化反应，与不对称醛的crotylation和交叉复分解相结合，可以提供具有高非对映选择性的单保护的2-甲基-1,3-二醇（从简单的醛开始）。
• Palladium/Norbornene Cooperative Catalysis To Access Tetrahydronaphthalenes and Indanes with a Quaternary Center
  作者：Ze-Shui Liu、Guangyin Qian、Qianwen Gao、Peng Wang、Hong-Gang Cheng、Qiang Wei、Qi Liu、Qianghui Zhou

  DOI：10.1021/acscatal.8b00975

  日期：2018.6.1

  palladium/XPhos complex and 5-norbornene-2-carboxylic acid was developed. This system promotes a two-component annulation reaction, allowing the construction of tetrahydronaphthalenes and indanes that contain quaternary centers through consecutive Catellani-type C–H activation and redox-relay Heck reaction. Inexpensive 5-norbornene-2-carboxylic acid acts as a catalytic mediator (20 mol %) in this process. This mild

  开发了包含钯/ XPhos配合物和5-降冰片烯-2-羧酸的协同催化体系。该系统促进了两组分环化反应，从而通过连续的Catellani型C–H活化和氧化还原中继Heck反应，构建了含有四级中心的四氢萘和茚满。廉价的5-降冰片烯-2-羧酸在该方法中充当催化介体（20mol％）。这种温和的，可扩展的和化学选择性的方案与各种现成的芳基碘化物和烷基化试剂兼容。证明了该方法在阿片类镇痛肽唑嗪的4步合成中的应用。初步研究强调了将这种Catellani /氧化还原中继Heck级联反应对映选择性的未来前景。
• Enantioselective Synthesis of Bicyclo[6.1.0]nonane-9-carboxylic Acids via Me₂AlOTf-Promoted Intramolecular Friedel−Crafts Alkylation of Arenes with the γ-Lactone Moiety of 3-Oxabicyclo[3.1.0]hexan-2-ones
  作者：Eric Fillion、Rachel L. Beingessner

  DOI：10.1021/jo0351419

  日期：2003.11.1

  acids via Me2AlOTf-promoted intramolecular Friedel-Crafts alkylation of tethered pi-nucleophiles with the gamma-lactone moiety of 3-oxabicyclo[3.1.0]hexan-2-ones is described. The approach begins with the enantioselective synthesis of 3-oxabicyclo[3.1.0]hexan-2-ones bearing a tethered pi-nucleophile at the 6-position by intramolecular Rh(II)-catalyzed cyclopropanation of allylic diazoacetates, prepared

  一种通过Me2AlOTf促进的分子内Fried-Crafts烷基化的π-亲核基团与3-氧杂双环[3.1.0] hexan-描述了2个位。该方法首先通过分子内Rh（II）催化的烯丙基重氮乙酸酯的环丙烷化对映体选择性合成在6位带有拴系π-亲核试剂的3-氧杂双环[3.1.0]己-2-酮。 Z）-烯丙醇。Me2AlOTf诱导的分子内Friedel-Crafts环化反应可高产率提供中等大小的碳环和杂环，而无需高稀释度或缓慢的底物添加技术。提出了这种综合方法的范围和局限性。
• 5-Norbornene-2-carboxylic acid: Another catalytic mediator for Catellani-type reactions
  作者：Ze-Shui Liu、Guangyin Qian、Qianwen Gao、Peng Wang、Hong-Gang Cheng、Yu Hua、Qianghui Zhou

  DOI：10.1016/j.tet.2019.01.033

  日期：2019.3

  Mediators play a central role in Catellani-type reactions. Herein we reported the discovery of inexpensive 5-norbornene-2-carboxylic acid (N-4) as a general catalytic mediator (20 mol%) to facilitate ortho C-H activation and the following C-C bond formation of aryl iodides. Firstly, a cooperative catalytic system comprising N-4 and a palladium/XPhos complex was developed for the novel Catellani/redox-relay Heck cascade to construct tetrahydronaphthalenes and indanes that contain a quaternary carbon stereogenic center. The striking feature of this work was the avoidance of stoichiometric NBE mediator that are usually required for Catellani-type reactions. Then, preliminary results demonstrated that N-4 could act as a general catalytic mediator to replace NBE for other Catellani-type reactions, which will undoubtedly inspire future developments in the field of cooperative catalysis. Finally, control experiments indicated that the carboxylic acid moiety of N-4 plays an essential role in its ability to serve as a superior mediator. (C) 2019 Elsevier Ltd. All rights reserved.