(Z)-1-bromo-4-methoxybut-2-ene

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (Z)-1-bromo-4-methoxybut-2-ene
• 化学式: C₅H₉BrO
• 分子量: 165.03
• InChiKey: ZVVCKMQQESDUNA-IHWYPQMZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  7
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (Z)-1-bromo-4-methoxybut-2-ene 在 氯化亚砜 、 sodium hydride 作用下， 生成 (Z)-1-(4-Chloro-but-2-ynyloxy)-4-methoxy-but-2-ene
  参考文献：
  名称：

  通过钨介导的[3 + 3]环氧化物与链状炔烃的环加成反应合成双环吡喃衍生物。

  摘要：

  用容易获得的材料在短时间内制备了带有束缚的环氧化物的炔丙钨化合物。在各种路易斯酸的存在下，BF（3）.Et（2）O催化剂（25摩尔％）最有效地促进环氧基[3 + 3]与其束缚的炔丙基钨基团的环加成，以合理的产率提供双环吡喃钨化合物。该环化具有非对映选择性，并且对各种官能团具有耐受性。立体化学结果表明，环加成反应是通过炔丙基钨基团的外向攻击由环氧化物的开环引发的。使用不同的氧化剂将所得吡喃钨钨有机金属脱金属以产生各种双环吡喃基衍生物。如果在环化反应中使用手性环氧化物，则这种新方法可以快速合成双环含氧化合物的对映体。提出了一种机械模型来合理化这种[3 + 3]环加成反应的路径。

  DOI：

  10.1021/jo010698e
• 作为产物：
  描述：

  (Z)-4-methoxybut-2-en-1-ol 在 三溴化磷 作用下， 以 乙醚 为溶剂， 以86%的产率得到(Z)-1-bromo-4-methoxybut-2-ene
  参考文献：
  名称：

  N，N'-二烷基二酮哌嗪添加剂的烯酸酯阴离子在BHAS偶联反应中单电子转移的证据。

  摘要：

  设计的N，N'-二烷基二酮哌嗪（DKP）提供了DKP添加剂作为引发剂的作用的证据，该引发剂在碱诱导的均相芳族取代反应（包括卤代芳烃与芳烃的偶联）中通过电子转移起作用。

  DOI：

  10.1039/c7ob02209c

文献信息

• Catalytic Iron-Mediated Triene Carbocyclizations: Stereoselective Five-Membered Ring Forming Carbocyclizations
  作者：James M. Takacs、Young-Chan Myoung、Lawrence G. Anderson

  DOI：10.1021/jo00102a016

  日期：1994.11

  The full details of investigations into the regiochemistry and stereochemistry of iron-catalyzed carbocyclizations of 2,7,9-decatriene derivatives to form five-membered carbocyclic ring systems are described. The roles of the allylic substituent, the alkene geometry, diene substitution, and the influence of resident stereogenic centers incorporated in the tether chain connecting the reacting 1,3-diene and alkene subunits are discussed.
• Copper-Catalyzed Regiospecific and 1,2-Regioselective Cyclopropanation of (1Z)-1-Amino- and (1Z)-1-Oxy-1,3-butadienyl Derivatives
  作者：Eiji Tayama、Shun Saito

  DOI：10.1055/s-0034-1380426

  日期：——

  The copper-catalyzed regiospecific and 1,2-regioselective cyclopropanation of (1Z)-1-amino- and (1Z)-1-oxy-1,3-butadienyl derivatives, which could be prepared by Z-stereoselective 1,4-elimination with a-aryl diazoesters was successfully demonstrated. This successful regiospecific protocol enabled the preparation of the corresponding 1-amino- and 1-oxy-2-vinylcyclopropane derivatives as almost single stereoisomers.
• Stereoselective preparation of (1Z)- and (1E)-N-Boc-1-amino-1,3-dienes by stereospecific base-promoted 1,4-elimination
  作者：Eiji Tayama、Yuka Toma

  DOI：10.1016/j.tet.2014.12.039

  日期：2015.1

  The base-promoted 1,4-elimination reaction of N-Boc-1-amino-4-methoxy-2-alkene 1 is shown to proceed with perfect stereoselectivity to afford the corresponding N-Boc-1-amino-1,3-diene 2 in good yields. The reaction is highly stereospecific. The substrate E-1 gave 1Z-2 by the 'Syn-Effect' and Z-1 gave 1E-2 via formation of a chelated intermediate. Our method is widely applicable to the preparation of various types of N-Boc-1-amino-1,3-dienes 2. (C) 2014 Elsevier Ltd. All rights reserved.
• Catalytic Iron-Mediated Enediene Carbocyclizations: Investigations into the Stereoselective Formation of Bicyclic Ring Systems
  作者：James M. Takacs、John J. Weidner、Peter W. Newsome、Beckie E. Takacs、Ramakrishnan Chidambaram、Richard Shoemaker

  DOI：10.1021/jo00116a039

  日期：1995.6

  Trienes in which the requisite 1,3-diene and allylic ether moieties are appended to a pre-existing ring system afford bicyclic ring systems-upon iron-catalyzed cyclization. The efficiency and stereoselectivity of the cyclization are dramatically influenced by the nature of the ring system to which the diene and alkene subunits are appended. Certain bicyclic ring systems are formed in good yield; most notably, substrates bearing a basic nitrogen are well-tolerated and certain indolizidine and quinolizidine ring systems are accessible using this methodology. The efficiency and stereoselectivity of the cyclization is also markedly dependent on the ligand used to modify the iron catalyst, and in this regard, a bisoxazoline-modified iron catalyst system is generally superior to what was the standard bipyridine-modified catalyst. In the course of these studies a difference spin polarization transfer (DSPT) experiment proved very useful for the stereochemical analysis of compounds that exhibit very crowded high field NMR spectra.
• Copper(II)–acid catalyzed cyclopropanation of 1,3-dienamides by electrophilic activation of α-aryl diazoesters
  作者：Eiji Tayama、Kouki Horikawa、Hajime Iwamoto、Eietsu Hasegawa

  DOI：10.1016/j.tetlet.2014.03.115

  日期：2014.5

  Copper(II)-acid catalyzed cyclopropanation of electron-rich alkenes, such as 1,3-dienamides, with cc-aryl diazoesters are described. The reaction could be performed without rare metal catalysts, excess substrate, or the need for the slow addition of the diazoesters. (C) 2014 Elsevier Ltd. All rights reserved.