(Z)-4-(but-2'-yn-1'-oxy)-but-2-en-1-yl acetate | 499794-48-8

• 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: (Z)-4-(but-2'-yn-1'-oxy)-but-2-en-1-yl acetate
• 英文别名: [(Z)-4-but-2-ynoxybut-2-enyl] acetate
• CAS: 499794-48-8
• 化学式: C₁₀H₁₄O₃
• 分子量: 182.219
• InChiKey: HMTMIYFVZBCVHF-WAYWQWQTSA-N

物化性质

• 沸点：
  253.4±30.0 °C(Predicted)
• 密度：
  1.010±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-4-(but-2'-yn-1'-oxy)-but-2-en-1-yl acetate 在 2,2'-联吡啶 、 palladium diacetate 、 溶剂黄146 作用下， 反应 12.0h， 以94%的产率得到3-(1'-acetoxy-ethylidene)-4-vinyl-tetrahydrofuran
  参考文献：
  名称：

  Cycloisomerization of 1,6-Enynes Using Acetate as a Nucleophile under Palladium(II) Catalysis

  摘要：

  An efficient method for the synthesis of five-membered carbo- and heterocyclic compounds, including fused rings, was reported using acetate as a nucleophile in the cyclization of 1,6-enynes under palladium(II) catalysis. The reaction is initiated by trans-acetoxypalladation of the alkynes and quenched by either trans- or cis-deacetoxypalladation in the presence of 2,2'-bipyridine as the ligand. An example of the catalytic asymmetric cyclization is presented with moderate enantioselectivity using chiral bisoxazoline ligand.

  DOI：

  10.1021/jo048414o
• 作为产物：
  描述：

  乙酸酐 、 (Z)-4-(but-2'-yn-1'-oxy)-but-2-en-1-ol 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以95%的产率得到(Z)-4-(but-2'-yn-1'-oxy)-but-2-en-1-yl acetate
  参考文献：
  名称：

  Cycloisomerization of 1,6-Enynes Using Acetate as a Nucleophile under Palladium(II) Catalysis

  摘要：

  An efficient method for the synthesis of five-membered carbo- and heterocyclic compounds, including fused rings, was reported using acetate as a nucleophile in the cyclization of 1,6-enynes under palladium(II) catalysis. The reaction is initiated by trans-acetoxypalladation of the alkynes and quenched by either trans- or cis-deacetoxypalladation in the presence of 2,2'-bipyridine as the ligand. An example of the catalytic asymmetric cyclization is presented with moderate enantioselectivity using chiral bisoxazoline ligand.

  DOI：

  10.1021/jo048414o

文献信息

• Pd-Catalyzed Borylative Cyclization of 1,6-Enynes
  作者：Juan Marco-Martínez、Verónica López-Carrillo、Elena Buñuel、Raquel Simancas、Diego J. Cárdenas

  DOI：10.1021/ja0685598

  日期：2007.2.1

  Pd-catalyzed cyclization of 1,6-enynes in the presence of bis(pinacolato)diboron affords homoallylic alkylboronates. The reaction is general and proceeds with differently substituted alkenes and with both internal and terminal alkynes. It tolerates the presence of β-hydrogens and is stereoselective in the formation of both the new stereogenic centers and the alkene. This synthesis of alkylboronates

  在双（频哪醇）二硼存在下，钯催化的 1,6-烯炔环化得到高烯丙基烷基硼酸酯。该反应是通用的，并且使用不同取代的烯烃以及内部和末端炔烃进行。它耐受β-氢的存在，并且在形成新的立体中心和烯烃时具有立体选择性。这种烷基硼酸酯的合成避免了使用高度亲核试剂​​并且与大多数官能团相容。
• The use of iminopyridines as efficient ligands in the palladium(II)-catalyzed cyclization of (Z)-4′-acetoxy-2′-butenyl 2-alkynoates
  作者：Juan Song、Qi Shen、Fan Xu、Xiyan Lu

  DOI：10.1016/j.tet.2007.04.006

  日期：2007.6

  Iminopyridines were found to be a sort of efficient bidentate ligands for the palladium(II)-catalyzed cyclization of (Z)-4′-acetoxy-2′-butenyl 2-alkynoates in acetic acid to afford the α-(Z)-acetoxyalkylidene-β-vinyl-γ-butyrolactones. The iminopyridine ligands could not only inhibit β-hydride elimination but also stabilize the vinyl-palladium intermediate in acetic acid in the reaction.

  发现氨基吡啶是一种有效的二齿配体，可用于钯（II）催化乙酸中的（Z）-4'-乙酰氧基-2'-丁烯基2-炔酸酯的环化反应，得到α-（Z）-乙酰氧基亚烷基-β-乙烯基-γ-丁内酯。亚氨基吡啶配体不仅可以抑制β-氢化物的消除，而且可以稳定反应中乙酸中的乙烯基-钯中间体。
• Highly Enantioselective Rh-Catalyzed Intramolecular Alder–Ene Reactions for the Syntheses of Chiral Tetrahydrofurans
  作者：Aiwen Lei、Minsheng He、Shulin Wu、Xumu Zhang

  DOI：10.1002/1521-3773(20020916)41:18<3457::aid-anie3457>3.0.co;2-3

  日期：2002.9.16