2-(溴甲基)辛-1-烯 | 71186-14-6

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机溴化物
• 中文名称: 2-(溴甲基)辛-1-烯
• 英文名称: 2-(bromomethyl)oct-1-ene
• CAS: 71186-14-6
• 化学式: C₉H₁₇Br
• 分子量: 205.138
• InChiKey: XDWSPANBQSDCMW-UHFFFAOYSA-N

物化性质

• 沸点：
  105-110 °C(Press: 22 Torr)
• 密度：
  1.073 g/cm3(Temp: 15 °C)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  10
• 可旋转键数：
  6
• 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：

  2-(溴甲基)辛-1-烯 在 蔗糖 Saccharomyces cerevisiae 、 硝酸铵 、 citric monohydrate 、 碳酸氢钠 、 碳酸氢铵 作用下， 以 乙醇 、 水 、 二甲基亚砜 为溶剂， 反应 132.0h， 生成 (R)-2-methyloctan-1-ol
  参考文献：
  名称：

  The synthesis of the insect pheromone (2S,3R,7R)-3,7-dimethyltridec-2-yl acetate from racemic 3,4-dimethyl-γ-butyrolactone by diastereoselective chiral resolution

  摘要：

  The insect pheromone (2S,3R,7R)-3,7-dimethyltridec-2-yl acetate 1-Ac was prepared from diastereomerically enriched (2S*,3R*,7R)-1, which in turn was obtained by the coupling of racemic 3,4-dimethyl-gamma-butyrolactone with (7S)-2-methyloctyllithium, followed by a Wolff-Kishner reduction of the resulting ketone. Conversion of (2S*,3R*,7R)-1 to the corresponding alkyl hydrogen phthalate and diastereomer salt formation with (S)-PhCHMeNH2 provided after several crystallizations individual diastereomer, which was later transformed into target 1-Ac after hydrolysis and acylation. (c) 2006 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2006.11.005
• 作为产物：
  描述：

  庚酸乙酯 在 titanium(IV) isopropylate 、 硫酸 、 三乙胺 、 magnesium bromide 作用下， 以 乙醚 为溶剂， 反应 4.0h， 生成 2-(溴甲基)辛-1-烯
  参考文献：
  名称：

  The synthesis of the insect pheromone (2S,3R,7R)-3,7-dimethyltridec-2-yl acetate from racemic 3,4-dimethyl-γ-butyrolactone by diastereoselective chiral resolution

  摘要：

  The insect pheromone (2S,3R,7R)-3,7-dimethyltridec-2-yl acetate 1-Ac was prepared from diastereomerically enriched (2S*,3R*,7R)-1, which in turn was obtained by the coupling of racemic 3,4-dimethyl-gamma-butyrolactone with (7S)-2-methyloctyllithium, followed by a Wolff-Kishner reduction of the resulting ketone. Conversion of (2S*,3R*,7R)-1 to the corresponding alkyl hydrogen phthalate and diastereomer salt formation with (S)-PhCHMeNH2 provided after several crystallizations individual diastereomer, which was later transformed into target 1-Ac after hydrolysis and acylation. (c) 2006 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2006.11.005

文献信息

• Synthesis and evaluation of phospholipid analogs as inhibitors of cobra venom phospholipase A2
  作者：Wei Yuan、Richard J. Berman、Michael H. Gelb

  DOI：10.1021/ja00260a020

  日期：1987.12

  Synthese d'analogues de phosphatidylcholine ou le groupe situe en 2 est remplace par des oxo-2 alkyle ou des hydroxy-2 alkyle

  Synthese d'analogues de phosphatidylcholine ou le groupe situen en 2 est remplace par des oxo-2alkane ou des hydroxy-2烷基
• Copper-Catalyzed Enantiotopic-Group-Selective Allylation of <i>gem</i>-Diborylalkanes
  作者：Minjae Kim、Bohyun Park、Minkyeong Shin、Suyeon Kim、Junghoon Kim、Mu-Hyun Baik、Seung Hwan Cho

  DOI：10.1021/jacs.0c11750

  日期：2021.1.20

  We report a copper-catalyzed enatiotopic-group-selective allylation of gem-diborylalkanes with allyl bromides. The combination of copper(I) bromide and H8-BINOL derived phosphoramidite ligand proved to be the most effective catalytic system to provide various enantioenriched homoallylic boronate esters, containing a boron-substituted stereogenic center that is solely derived from gem-diborylalkanes

  我们报告了铜催化的对映基团选择性烯丙基化的 gem-二硼烷烃与烯丙基溴。溴化铜 (I) 和 H8-BINOL 衍生的亚磷酰胺配体的组合被证明是提供各种对映体富集的高烯丙基硼酸酯的最有效的催化系统在温和条件下具有高对映体比率。已经进行了实验和理论研究以阐明反应机理，揭示了宝石-二硼烷基烷烃与手性铜配合物的对映基团选择性转移金属是如何发生手性 α-硼烷基-铜物种的。还包括合成各种手性构件的其他合成应用。
• Asymmetric Linear-Selective Hydroformylation of 1,1-Dialkyl Olefins Assisted by a Steric-Auxiliary Strategy
  作者：Dequan Zhang、Cai You、Xiuxiu Li、Jialin Wen、Xumu Zhang

  DOI：10.1021/acs.orglett.0c01550

  日期：2020.6.5

  Asymmetric hydroformylation of 1,2-dialkyl olefins was reported. In order to increase the enantiomeric induction, steric auxiliary sulfonyl groups were introduced. Using a Rh/Yanphos complex as catalyst, chiral aldehydes were obtained with high enantioselectivities under mild pressure. The easily removable auxiliary made this method a powerful tool in the preparation of important enantiopure building

  据报道1,2-二烷基烯烃的不对称加氢甲酰化。为了增加对映异构体的诱导，引入了空间辅助磺酰基。使用Rh / Yanphos络合物作为催化剂，在适度的压力下获得具有高对映选择性的手性醛。易于去除的助剂使该方法成为制备重要对映纯构件的强大工具。
• Dynamic Kinetic Resolution of Aldehydes by Hydroacylation
  作者：Zhiwei Chen、Yusuke Aota、Hillary M. H. Nguyen、Vy M. Dong

  DOI：10.1002/anie.201900545

  日期：2019.3.26

  We report a dynamic kinetic resolution (DKR) of chiral 4‐pentenals by olefin hydroacylation. A primary amine racemizes the aldehyde substrate via enamine formation and hydrolysis. Then, a cationic rhodium catalyst promotes hydroacylation to generate α,γ‐disubstituted cyclopentanones with high enantio‐ and diastereoselectivities.

  我们通过烯烃加氢酰化反应报告了手性4-戊烯醛的动态动力学拆分（DKR）。伯胺通过烯胺的形成和水解使醛底物消旋。然后，阳离子铑催化剂促进加氢酰化反应生成具有高对映异构和非对映异构选择性的α，γ-二取代环戊酮。
• Direct carboxylation of allylic halides with carbon dioxide in the presence of indium
  作者：Bukeyan Miao、Shengming Ma

  DOI：10.1039/c4cc00148f

  日期：——

  A highly regioselective indium-mediated allylation of carbon dioxide starting from simple allylic halides (X = I, Br, Cl) has been developed. No transition metal catalyst is needed and an inert atmosphere is not necessary. The reaction tolerates a wide range of synthetically attractive functional groups with a very high branched regioselectivity.

  一种高区域选择性的铟介导的二氧化碳烯丙基化反应已被开发，该反应以简单的烯丙卤化物（X = I, Br, Cl）为起始物。不需要过渡金属催化剂，也不需要惰性气氛。该反应能够耐受广泛的合成上具有吸引力的功能团，并具有非常高的支化区域选择性。