3-butylcyclohex-2-en-1-yl acetate | 141091-11-4

• 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: 3-butylcyclohex-2-en-1-yl acetate
• 英文别名: 1-acetoxy-3-butyl-cyclohex-2-ene；(3-Butylcyclohex-2-en-1-yl) acetate
• CAS: 141091-11-4
• 化学式: C₁₂H₂₀O₂
• 分子量: 196.29
• InChiKey: ZSNQUNPRDSDEMF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  烯丙基硼酸频哪醇酯 、 3-butylcyclohex-2-en-1-yl acetate 在 (allylPdCl)2 、 1,2-双(二苯基膦基)苯 、 水 、 cesium fluoride 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以59%的产率得到3-allyl-3-butylcyclohex-1-ene
  参考文献：
  名称：

  Catalytic Stereospecific Allyl–Allyl Cross-Coupling of Internal Allyl Electrophiles with AllylB(pin)

  摘要：

  Application of internal electrophiles in catalytic stereospecific allyl allyl cross-coupling enable the rapid construction of multisubstituted 1,5-dienes, including those with all carbon quaternary centers. Compounds with minimal steric differentiation can be synthesized with high enantiomeric excess.

  DOI：

  10.1021/ol500456s
• 作为产物：
  描述：

  1-butyl-2-cyclohexen-1-ol 在 4-二甲氨基吡啶 、 三乙胺 、 水杨酸 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 15.0h， 生成 3-butylcyclohex-2-en-1-yl acetate
  参考文献：
  名称：

  Catalytic Stereospecific Allyl–Allyl Cross-Coupling of Internal Allyl Electrophiles with AllylB(pin)

  摘要：

  Application of internal electrophiles in catalytic stereospecific allyl allyl cross-coupling enable the rapid construction of multisubstituted 1,5-dienes, including those with all carbon quaternary centers. Compounds with minimal steric differentiation can be synthesized with high enantiomeric excess.

  DOI：

  10.1021/ol500456s

文献信息

• Lewis acid-catalyzed oxidative rearrangement of tertiary allylic alcohols mediated by TEMPO
  作者：Jean-Michel Vatèle

  DOI：10.1016/j.tet.2009.11.104

  日期：2010.1

  Two methods for the oxidative rearrangement of tertiary allylic alcohols have been developed. Most of tertiary allylic alcohols studied were oxidized to their corresponding transposed carbonyl derivatives in excellent to fair yields by reaction with TEMPO in combination with PhIO and Bi(OTf)3 or copper (II) chloride in the presence or not of oxygen. Other primary oxidants of TEMPO such as PhI(OAc)2

  已经开发了两种方法用于叔烯丙基醇的氧化重排。通过与TEMPO结合PhIO和Bi（OTf）3或氯化铜（II）在氧气存在或不存在的情况下反应，可以将所研究的大多数叔烯丙醇氧化成其相应的转座羰基衍生物，收率极好至合理。TEMPO的诸如岛（OAC）等初级氧化剂2，中号CPBA，过硫酸氢钾®不能令人满意给予烯酮在适度低的产率。
• TEMPO/NaIO₄−SiO₂: A Catalytic Oxidative Rearrangement of Tertiary Allylic Alcohols to β-Substituted α,β-Unsaturated Ketones
  作者：Masatoshi Shibuya、Masaki Tomizawa、Yoshiharu Iwabuchi

  DOI：10.1021/ol801673r

  日期：2008.11.6

  The novel catalytic method for the oxidative rearrangement of tertiary allylic alcohols to beta-substituted alpha,beta-unsaturated ketones is described. TEMPO/NaIO4-SiO2 causes facile and efficient oxidative rearrangement of various acyclic substrates as well as medium-sized and macrocyclic substrates.

  描述了一种新的催化方法，用于将叔烯丙基醇氧化重排为β-取代的α，β-不饱和酮。TEMPO / NaIO4-SiO2导致各种无环底物以及中型和大环底物的便捷有效氧化重排。
• Lithium perchlorate-assisted substitution reactions of allylic acetates and allylic alcohols
  作者：William H. Pearson、Jeffrey M. Schkeryantz

  DOI：10.1021/jo00037a004

  日期：1992.5

  Substitution reactions of allylic acetates and allylic alcohols by a variety of nucleophiles proceed smoothly in the presence of lithium perchlorate in ether, providing a convenient alternative to transition metal catalyzed methods.