2-苄基-1-乙氧基乙烯 | 18232-27-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-苄基-1-乙氧基乙烯
• 英文名称: 2-benzyl-1-ethoxyethylene
• 英文别名: 1-Ethoxy-3-phenyl-prop-1-en；1-Ethoxy-3-phenyl-prop-2-en；1-Ethoxy-3-phenylprop-1-en；p-Ethoxyallylbenzene；3-ethoxyprop-2-enylbenzene
• CAS: 18232-27-4
• 化学式: C₁₁H₁₄O
• 分子量: 162.232
• InChiKey: BZKGPTKCEFKPCG-UHFFFAOYSA-N

物化性质

• 沸点：
  110 °C(Press: 16 Torr)
• 密度：
  0.944±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  2-苄基-1-乙氧基乙烯 在 盐酸 作用下， 以 吡啶 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 苯丙醛
  参考文献：
  名称：

  Nickel-Catalyzed Arylation of Acrolein Diethyl Acetal:  A Substitute to the 1,4-Addition of Arylhalides to Acrolein

  摘要：

  In the presence of catalytic amount of NiBr2 as Catalyst precursor, organic halides are reductively coupled at 70 degreesC with acrolein diethyl acetal to give (Z)- and (E)-enolethers by allylic deplacement of an alkoxy group. Subsequent hydrolysis affords beta-arylated aldehydes.

  DOI：

  10.1021/ol035877s
• 作为产物：
  描述：

  3-Cyclohexen-(1)-yl-propin-(2)-al-(1)-diethylacetal 生成 2-苄基-1-乙氧基乙烯
  参考文献：
  名称：

  Mantione,R. et al., Bulletin de la Societe Chimique de France, 1967, p. 2912 - 2918

  摘要：

  DOI：

文献信息

• Cobalt- and rhodium-catalyzed cross-coupling reaction of allylic ethers and halides with organometallic reagents
  作者：Hiroto Yasui、Keiya Mizutani、Hideki Yorimitsu、Koichiro Oshima

  DOI：10.1016/j.tet.2005.11.032

  日期：2006.2

  Reactions of 2-alkenyl methyl ether with phenyl, trimethylsilylmethyl, and allyl Grignard reagents in the presence of cobalt(II) complexes are discussed. The success of the reactions heavily depends on the combination of the substrate, ligand, and Grignard reagent. In the reaction of cinnamyl methyl ether, the formation of the linear coupling products predominates over that of the relevant branched

  讨论了2-烯基甲基醚与苯基，三甲基甲硅烷基甲基和烯丙基格氏试剂在钴（II）配合物存在下的反应。反应的成功在很大程度上取决于底物，配体和格氏试剂的组合。在肉桂基甲基醚的反应中，线性偶联产物的形成比相关支链产物的形成更占优势。在烯丙基醚的钴催化的烯丙基化中，添加二膦配体可以改变区域选择性，主要提供相应的支链产物。铑配合物分别催化烯丙基醚和卤化物与烯丙基氯化镁和烯丙基溴化锌的反应，其中支链偶联产物是主要产物。
• Palladium-Catalyzed Difunctionalization of Enol Ethers to Amino Acetals with Aminals and Alcohols
  作者：Yinjun Xie、Jianhua Hu、Pan Xie、Bo Qian、Hanmin Huang

  DOI：10.1021/ja410611b

  日期：2013.12.11

  generated in Heck reaction via nucleophilic addition prior to the step of migratory insertion, which leads to a new palladium-catalyzed difunctionalization of enol ethers with aminals and alcohols to afford amino acetals. Mechanistic studies suggested that the cationic cyclometalated Pd(II) complex generated by the oxidative addition of aminal to a Pd(0) species was crucial for this unusual transformation

  开发了一种新策略，用于在迁移插入步骤之前通过亲核加成拦截 Heck 反应中生成的钯-烷基物质，这导致新的钯催化的烯醇醚与胺和醇的双官能化以提供氨基缩醛。机理研究表明，通过将氨基氧化加成到 Pd(0) 物种中产生的阳离子环金属化 Pd(II) 络合物对于这种不寻常的转化至关重要。
• Fluoroolefin dipeptide isosteres -II.
  作者：Thomas Allmendinger、Eduard Felder、Ernst Hungarbühler

  DOI：10.1016/s0040-4039(00)88549-4

  日期：1990.1

  hydroxyl group thus formed by a trichloro-acetamido group via Overman rearrangement constitutes a new general route to fluoroofefin dipeptide isosteres in enantiomerically pure form. This methodology was applied for the preparation of both enantiomars of the Phe…(CFCH)Gly dipeptide mimic which were further elongated to substance P analogues.

  向α-氟代-α，β-不饱和醛中添加旋光酯烯醇，再由三氯乙酰胺基通过超载重排形成的烯丙基羟基进行正式的S N 2'取代，构成了制备氟代蝶呤二肽等排体的新途径呈对映体纯形式。该方法学用于制备Phe…（CFCH）Gly二肽模拟物的两个对映体，并进一步延长为P物质类似物。
• Quelet,R. et al., Bulletin de la Societe Chimique de France, 1966, p. 3258 - 3264
  作者：Quelet,R. et al.

  DOI：——

  日期：——
• Alkylation of 2-oxy-substituted 1-sulfonylallyl and 1-sulfonylvinyl anions. New routes to functionalized carbocycles and dihydrofurans
  作者：Albert Padwa、William H. Bullock、Andrew D. Dyszlewski、S. W. McCombie、B. B. Shankar、A. K. Ganguly

  DOI：10.1021/jo00011a021

  日期：1991.5

  Alkylation of the anion derived from 2-phenoxy-3-(phenylsulfonyl)-1-propene proceeds alpha to the phenylsulfonyl group and affords cyclic products from 1,omega-dihalides. Reaction of the monoalkylated products, in which a suitably positioned olefinic or acetylenic unit is present, with sodium benzenesulfinate-acetic acid gives functionalized acetylcyclopentenes and cyclohexenes via C-C bond formation from the allyl cation-sulfinate ion pair. In the vinyl sulfone series, deprotonation of (E)- or (Z)-2-alkoxyvinyl phenyl sulfones rapidly affords the more stable (E)-lithio derivative, an acetaldehyde anion equivalent which reacts normally with aldehydes, ketones, alkyl halides, and epoxides. The latter process may be effected in an intramolecular fashion. Thus, (E)-(2-phenylsulfonyl) vinyl ethers of 2,3-epoxy alcohols cyclize on treatment with amide bases to afford dihydrofurans whose stereochemistry is fully defined by that of the starting epoxy alcohol.