(E)-1-bromo-2-methyloct-1-ene | 1081763-04-3

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: (E)-1-bromo-2-methyloct-1-ene
• CAS: 1081763-04-3
• 化学式: C₉H₁₇Br
• 分子量: 205.138
• InChiKey: ISTCARXXRIJZJQ-CMDGGOBGSA-N

物化性质

• 沸点：
  92-93 °C(Press: 20 Torr)
• 密度：
  1.103 g/cm3(Temp: 18 °C)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (E)-1-bromo-2-methyloct-1-ene 在 C₃₄H₃₈Cl₂F₆FeP₂Pd 、 臭氧 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 为溶剂， 反应 54.21h， 生成 (R)-2-methyloctane-1,2-diol
  参考文献：
  名称：

  Nonracemic Allylic Boronates through Enantiotopic-Group-Selective Cross-Coupling of Geminal Bis(boronates) and Vinyl Halides

  摘要：

  Under the influence of a chiral palladium catalyst, 1,1-bis(pinacolboronate) esters undergo asymmetric cross-coupling with bromoalkenes to generate nonracemic allyl boronates with high levels of enantioselectivity. The so-formed allyl boronates may be oxidized with hydrogen peroxide to provide secondary allylic alcohols or with nitrosobenzene to furnish nonracemic tertiary allylic alcohols. Mechanistic experiments suggest the operation of a pathway involving outer-sphere stereoinvertive transmetalation.

  DOI：

  10.1021/ja510266x
• 作为产物：
  描述：

  (E)-(2-methyl-1-octenyl)dimethylalane 在 甲磺酰溴 作用下， 反应 0.25h， 生成 (E)-1-bromo-2-methyloct-1-ene
  参考文献：
  名称：

  Efficient halogenation of unsaturated organoaluminum compounds with sulfonyl halides

  摘要：

  Alkenylalumanes prepared by carbo-or cycloalumination of substituted acetylenes reacted with an equivalent amount of sulfonyl halide (MsCl, TsCl, PhSO2Cl, MsBr) in methylene chloride or hexane at room temperature to produce alkenyl halides in high yields. Electron-donor solvents such as diethyl ether or tetrahydrofuran inhibited the halogenation process. beta-Substituted vinylalumanes generated by hydroalumination of substituted acetylenes failed to react with sulfonyl halides.

  DOI：

  10.1134/s1070428013030020

文献信息

• Pd‐Catalyzed Negishi Cross‐Coupling of Vinyl Bromides with Diborylmethylzinc Chloride
  作者：Minjae Kim、Jun Hee Lee、Seung Hwan Cho

  DOI：10.1002/bkcs.12212

  日期：2021.3

  We have developed Pd‐catalyzed Negishi cross‐coupling of diborylmethylzinc chloride with vinyl bromides. The reaction shows a broad scope and an array of α‐boryl‐substituted allylic boronate esters are obtained in high efficiency.

  我们已经开发了二硼烷基甲基氯化锌与乙烯基溴化物在Pd催化下的Negishi交叉偶联。该反应显示出广阔的范围，并且可以高效地获得一系列α-硼基取代的烯丙基硼酸酯。
• Single‐Flask Multicomponent Palladium‐Catalyzed α,γ‐Coupling of Ketone Enolates: Facile Preparation of Complex Carbon Scaffolds
  作者：Michael Grigalunas、Per‐Ola Norrby、Olaf Wiest、Paul Helquist

  DOI：10.1002/anie.201505895

  日期：2015.9.28

  A three‐component palladium‐catalyzed reaction sequence has been developed in which γ‐substituted α,β‐unsaturated products are obtained in a single flask by an α‐alkenylation with either a subsequent γ‐alkenylation or γ‐arylation of a ketone enolate. Coupling of a variety of electronically and structurally different components was achieved in the presence of a Pd/Q‐Phos catalyst (2 mol %), usually

  已开发出一种三组分钯催化的反应序列，其中在单个烧瓶中通过α-烯基化以及随后的γ-烯基化或酮烯酸酯的γ-芳基化在单个烧瓶中获得γ-取代的α，β-不饱和产物。在Pd / Q-Phos催化剂（2 mol％）的存在下，通常在22°C时，各种电子和结构上不同的组件可以实现偶联，收率最高为85％。最重要的是，通过一种简单的操作即可代替使用多个反应，从而获得这些产品。
• Practical Synthesis of Chiral Allylboronates by Asymmetric 1,1‐Difunctionalization of Terminal Alkenes
  作者：Caocao Sun、Yuqiang Li、Guoyin Yin

  DOI：10.1002/anie.202209076

  日期：2022.9.12

  A highly 1,1-regio- and enantioselective alkenylboration of undirected and unactivated alkenes has been developed, which allows chiral allylboronates to be efficiently synthesized from readily available terminal alkenes, alkenyl bromides and B2pin2. This method is distinguished by its use of an inexpensive chiral catalyst, readily available starting materials, mild and convenient reaction conditions

  已经开发了一种高度 1,1-区域和对映选择性的无向和未活化烯烃的烯基硼化反应，它允许从容易获得的末端烯烃、烯基溴化物和 B 2 pin 2有效地合成手性烯丙基硼酸酯。该方法的特点是使用廉价的手性催化剂、容易获得的起始材料、温和方便的反应条件、可扩展性和实用性。