1-ethyl-2,3-butadienyl acetate | 99893-57-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1-ethyl-2,3-butadienyl acetate
• CAS: 99893-57-9
• 化学式: C₈H₁₂O₂
• 分子量: 140.182
• InChiKey: HFTXUMBGGQEHFK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-ethyl-2,3-butadienyl acetate 在 palladium diacetate 、 lithium bromide 作用下， 以 溶剂黄146 为溶剂， 反应 6.0h， 生成 (3E)-2-bromo-1,3-hexadiene
  参考文献：
  名称：

  Palladium(II)-Catalyzed S_N2‘ Reactions of α-Allenic Acetates. Stereoconvergent Synthesis of (Z,E)-2-Bromo-1,3-dienes

  摘要：

  The reaction of acetylated a-allenic alcohols with LiBr in the presence of 1.5 mol % of Pd(OAc)(2) provides easy access to substituted (Z,E)-2-bromo-1,3-dienes in good yields with excellent diastereoselectivity. Both secondary and tertiary acetates as well as terminal and nonterminal allenes were studied to investigate the scope and the limitations of the reaction. A mechanism is proposed to clarify how a diastereomeric mixture of the starting compound is transformed into a single diastereomer of the product.

  DOI：

  10.1021/jo015950x
• 作为产物：
  描述：

  乙基乙炔基甲醇 在 吡啶 、 4-二甲氨基吡啶 、 二异丙胺 、 copper(I) bromide 作用下， 以 1,4-二氧六环 为溶剂， 生成 1-ethyl-2,3-butadienyl acetate
  参考文献：
  名称：

  Palladium(II)-Catalyzed S_N2‘ Reactions of α-Allenic Acetates. Stereoconvergent Synthesis of (Z,E)-2-Bromo-1,3-dienes

  摘要：

  The reaction of acetylated a-allenic alcohols with LiBr in the presence of 1.5 mol % of Pd(OAc)(2) provides easy access to substituted (Z,E)-2-bromo-1,3-dienes in good yields with excellent diastereoselectivity. Both secondary and tertiary acetates as well as terminal and nonterminal allenes were studied to investigate the scope and the limitations of the reaction. A mechanism is proposed to clarify how a diastereomeric mixture of the starting compound is transformed into a single diastereomer of the product.

  DOI：

  10.1021/jo015950x

文献信息

• Catalytic Asymmetric Allenylation of Malonates with the Generation of Central Chirality
  作者：Qiankun Li、Chunling Fu、Shengming Ma

  DOI：10.1002/anie.201204346

  日期：2012.11.19

  Water plays an important role in a palladium‐catalyzed allenylation of diethyl malonate with 2,3‐allenyl acetates to yield centrally chiral allenyl malonates bearing synthetically useful functional groups (see scheme). The products were formed with 92–96 % ee in the presence of a bulky, electron‐rich biphenyl ligand at room temperature.

  水在钯催化的丙二酸二乙酯与2，3-烯丙基乙酸酯的烯丙基化反应中起重要作用，以产生带有合成有用官能团的中心手性烯丙二酸酯（参见方案）。在室温下，在存在大量电子富集的联苯配体的情况下，形成的产品具有92％至96％  ee。
• Stereodivergent Synthesis of Allenes with α,β‐Adjacent Central Chiralities Empowered by Synergistic Pd/Cu Catalysis
  作者：Ling Zhao、Yicong Luo、Junzhe Xiao、Xiaohong Huo、Shengming Ma、Wanbin Zhang

  DOI：10.1002/anie.202218146

  日期：2023.2.20

  An efficient Pd/Cu co-catalyzed dynamic kinetic allenylic alkylation of racemic allenylic acetates with aldimine esters has been developed. Various allenes bearing α,β-adjacent central chiralities were obtained with excellent stereoselectivities. The easy interconversion between the uncommon η3-butadienyl palladium intermediates featuring a weak C=C/Pd coordination bond and a stable Csp2−Pd bond is

  开发了一种有效的 Pd/Cu 共催化的外消旋丙二烯乙酸酯与醛亚胺酯的动态动态丙二烯烷基化反应。获得了具有 α,β-相邻中心手性的各种丙二烯，具有优异的立体选择性。具有弱 C=C/Pd 配位键和稳定的 Csp 2 -Pd 键的罕见η 3 -丁二烯基钯中间体之间的容易相互转化对于标题反应至关重要。
• Allylstannation
  作者：Andrea Boaretto、Daniele Marton、Giuseppe Tagliavini

  DOI：10.1016/0022-328x(85)80121-2

  日期：1985.6
• BOARETTO, A.;MARTON, D.;TAGLIAVINI, G., J. ORGANOMET. CHEM., 1985, 288, N 3, 283-287
  作者：BOARETTO, A.、MARTON, D.、TAGLIAVINI, G.

  DOI：——

  日期：——
• Palladium(II)-Catalyzed S_N2‘ Reactions of α-Allenic Acetates. Stereoconvergent Synthesis of (<i>Z</i>,<i>E</i>)-2-Bromo-1,3-dienes
  作者：Attila Horváth、Jan-E. Bäckvall

  DOI：10.1021/jo015950x

  日期：2001.11.1

  The reaction of acetylated a-allenic alcohols with LiBr in the presence of 1.5 mol % of Pd(OAc)(2) provides easy access to substituted (Z,E)-2-bromo-1,3-dienes in good yields with excellent diastereoselectivity. Both secondary and tertiary acetates as well as terminal and nonterminal allenes were studied to investigate the scope and the limitations of the reaction. A mechanism is proposed to clarify how a diastereomeric mixture of the starting compound is transformed into a single diastereomer of the product.