2-phenethyl-2-vinyloxirane | 1610376-65-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-phenethyl-2-vinyloxirane
• 英文别名: Vinylphenylethyloxirane；2-ethenyl-2-(2-phenylethyl)oxirane
• CAS: 1610376-65-2
• 化学式: C₁₂H₁₄O
• 分子量: 174.243
• InChiKey: BRMGQMZZCKCDDK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-phenethyl-2-vinyloxirane 在 sodium hydride 作用下， 以 四氢呋喃 、 甲苯 、 mineral oil 为溶剂， 反应 12.0h， 生成 2-(4-phenylbut-1-en-2-yl)thiirane
  参考文献：
  名称：

  Mild stereoselective formation of tri- and tetrasubstituted olefins by regioselective ring opening of 1,1-disubstituted vinyl oxiranes with dialkyl dithiophosphates

  摘要：

  Presented in this Letter is a mild new method to stereoselectively ring open 1,1-disubstituted vinyl oxiranes using dialkyl dithiophosphate nucleophiles. This new reaction proceeds in toluene at room temperature to afford tri- and tetrasubstituted allylic alcohols with high Z-selectivity. The syn relationship between the alcohol and the newly incorporated dithiophosphate moiety presented an opportunity to evaluate the anionic hopping properties of the ring opening product. Treatment of the ring opening product with base results in a facile phosphate hopping followed by a selective thiolate 3-exo-trig instead of a 5-exo-tet cyclization. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.04.028
• 作为产物：
  描述：

  5-phenyl-1-penten-3-one 在 正丁基锂 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醚 、 二甲基亚砜 、 mineral oil 为溶剂， 反应 0.37h， 生成 2-phenethyl-2-vinyloxirane
  参考文献：
  名称：

  Mild stereoselective formation of tri- and tetrasubstituted olefins by regioselective ring opening of 1,1-disubstituted vinyl oxiranes with dialkyl dithiophosphates

  摘要：

  Presented in this Letter is a mild new method to stereoselectively ring open 1,1-disubstituted vinyl oxiranes using dialkyl dithiophosphate nucleophiles. This new reaction proceeds in toluene at room temperature to afford tri- and tetrasubstituted allylic alcohols with high Z-selectivity. The syn relationship between the alcohol and the newly incorporated dithiophosphate moiety presented an opportunity to evaluate the anionic hopping properties of the ring opening product. Treatment of the ring opening product with base results in a facile phosphate hopping followed by a selective thiolate 3-exo-trig instead of a 5-exo-tet cyclization. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.04.028

文献信息

• Palladium/<i>N</i>-Heterocyclic Carbene (NHC)-Catalyzed Asymmetric [3 + 2] Cycloaddition Reaction of Vinyl Epoxides with Allenic Amides
  作者：Wan-Ying Wang、Jing-Yu Wu、Qing-Rong Liu、Xiu-Yan Liu、Chang-Hua Ding、Xue-Long Hou

  DOI：10.1021/acs.orglett.8b01886

  日期：2018.8.17

  Allenic amides are successfully developed as dipolarophiles to react with vinyl epoxides under Pd-catalysis. The chiral NHC showed its unique role as the ligand in this asymmetric [3 + 2] cycloaddition. Chiral tetrahydrofurans bearing three functional groups (monosubstituted alkene, tetrasubstituted enolether, and amide) and vicinal tertiary and quaternary stereocenters were obtained in high yields

  丙二烯酰胺已成功开发为双极性亲和剂，可在Pd催化下与乙烯基环氧化物反应。手性NHC在这种不对称的[3 + 2]环加成反应中显示出其作为配体的独特作用。具有高非对映和对映选择性的高收率获得了带有三个官能团（单取代的烯烃，四取代的烯醇醚和酰胺）和邻位的叔和季立体中心的手性四氢呋喃。
• Palladium-Catalyzed Ring-Opening Reaction of Cyclopropenones with Vinyl Epoxides
  作者：Li-Guo Lu、Jun-Hua Chen、Xiao-Bo Huang、Miao-Chang Liu、Yun-Bing Zhou、Hua-Yue Wu

  DOI：10.1021/acs.joc.2c01976

  日期：2022.12.16

  We report herein the Pd-catalyzed selective ring-opening reaction of cyclopropenones with vinyl epoxides. By using a commercially available Pd2(dba)3·CHCl3–BINAP catalyst, a wide range of conjugated alkadienyl carboxylates could be accessed in good yield and excellent regioselectivity. The new application of zwitterionic π-allyl palladium intermediates has been demonstrated in organic synthesis.

  我们在此报告了 Pd 催化的环丙烯酮与乙烯基环氧化物的选择性开环反应。通过使用市售的 Pd 2 (dba) 3 ·CHCl 3 –BINAP 催化剂，可以以良好的收率和出色的区域选择性获得各种共轭链二烯基羧酸盐。两性离子π-烯丙基钯中间体在有机合成中的新应用已得到证实。
• 不飽和エポキシ化合物、その製造方法および不飽和エポキシ化合物の（共）重合体
  申请人：——

  公开号：JP2000297082A

  公开（公告）日：2000-10-24

  (57)【要約】\n【課題】 感光性樹脂製造用モノマーとして期待できる炭素炭素二重結合を有する新規な不飽和エポキシ化合物、その製法およびこの化合物を用いた（共）重合体を提供すること。\n【解決手段】 ω−ハロマグネシウムアルキル（α-メチル）スチレンと（メチル）エピクロロヒドリンを反応させて、式（１）の化合物を製造する。\n【化１】\n（式中、ｎは１〜５の整数を表し、Ｒは水素原子またはメチル基を表し、さらにＱは水素原子またはメチル基をそれぞれ表す。）

  (57) [摘要] Јn[主题] 提供新的具有碳碳双键的不饱和环氧化合物，该化合物有望作为生产感光树脂的单体、其生产工艺以及使用这些化合物的（共）聚合物材料。\溶液]式（1）化合物是通过ω-卤镁烷基（α-甲基）苯乙烯与（甲基）环氧氯丙烷反应制得的。\式 1] Јn（其中 n 代表 1 至 5 的整数，R 代表氢原子或甲基，Q 分别代表氢原子或甲基）。
• Mild stereoselective formation of tri- and tetrasubstituted olefins by regioselective ring opening of 1,1-disubstituted vinyl oxiranes with dialkyl dithiophosphates
  作者：Boying Guo、Edon Vitaku、Jon T. Njardarson

  DOI：10.1016/j.tetlet.2014.04.028

  日期：2014.5

  Presented in this Letter is a mild new method to stereoselectively ring open 1,1-disubstituted vinyl oxiranes using dialkyl dithiophosphate nucleophiles. This new reaction proceeds in toluene at room temperature to afford tri- and tetrasubstituted allylic alcohols with high Z-selectivity. The syn relationship between the alcohol and the newly incorporated dithiophosphate moiety presented an opportunity to evaluate the anionic hopping properties of the ring opening product. Treatment of the ring opening product with base results in a facile phosphate hopping followed by a selective thiolate 3-exo-trig instead of a 5-exo-tet cyclization. (C) 2014 Elsevier Ltd. All rights reserved.