trans-2-chloro-1,1-diethoxy-2-butene | 7364-07-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: trans-2-chloro-1,1-diethoxy-2-butene
• 英文别名: (Z)-2-chloro-1,1-diethoxy-2-butene；(Z)-2-chloro-1,1-diethoxy-but-2-ene
• CAS: 7364-07-0
• 化学式: C₈H₁₅ClO₂
• 分子量: 178.659
• InChiKey: HAIVYUPYTLCQAF-DAXSKMNVSA-N

物化性质

• 沸点：
  200.4±40.0 °C(Predicted)
• 密度：
  1.000±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.53
• 重原子数：
  11.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  trans-2-chloro-1,1-diethoxy-2-butene 在 盐酸 作用下， 生成 (Z)-2-chlorobut-2-enal
  参考文献：
  名称：

  Chemistry of gem-Dihalocyclopropanes. IV. Ring Opening of gem-Dichlorocyclopropyl Ethers

  摘要：

  DOI：

  10.1021/jo01343a057
• 作为产物：
  描述：

  乙醇 、 1,1-dichloro-2-ethoxy-3-methylcyclopropane 在 吡啶 作用下， 以80%的产率得到trans-2-chloro-1,1-diethoxy-2-butene
  参考文献：
  名称：

  Neighbouring-group Influence on the Ring Opening of 2-Aryloxymethyl-1,1,2-tribromocyclopropanes under Phase-transfer Conditions.

  摘要：

  When a number of 2-aryloxymethyl-1,1,2-tribromocyclopropa were treated with sodium hydroxide and ethanol under phase-transfer conditions, ring opening occurred to give mixtures of acetylenic diethyl acetals and ketals in better than 80% total isolated yield. The acetylenic diethyl ketals predominated significantly and were, in some cases, almost the exclusive product. It is argued that this ketal selectivity is in part caused by hydrogen bonding between ethanol and the aryloxy group.

  DOI：

  10.3891/acta.chem.scand.53-0465

文献信息

• A New Platinum Complex Catalyzed Reaction Involving Nucleophilic Substitution at the Central Carbon Atom of the π-Allyl Ligand
  作者：Joji Kadota、Shinji Komori、Yoshiya Fukumoto、Shinji Murai

  DOI：10.1021/jo990845x

  日期：1999.10.1

  The reaction of 2-chloro-allyl acetate with sodium ethyl acetoacetate in the presence of a platinum(O) complex gave furan derivatives. The key feature of this-new platinum-catalyzed reaction is the nucleophilic substitution at the central carbon atom of pi-allyl complexes. The regioselectivity of the nucleophilic attacks (central or terminal) is dependent on the pK(a) of the nucleophile. In addition, a labeling experiment revealed that a rapid syn-anti isomerization of the (pi-allyl) platinum complexes occurs.