2-dodecylbuta-1,3-diene

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: 2-dodecylbuta-1,3-diene
• 英文别名: 3-Methylidenepentadec-1-ene
• 化学式: C₁₆H₃₀
• 分子量: 222.414
• InChiKey: CBDSKMTWQUERSQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  16
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  对甲基苯甲醛 、 2-dodecylbuta-1,3-diene 在 锰 、 2-(2-(diphenylphosphaneyl)phenyl)-4-isopropyl-4,5-dihydrooxazole 、 cobalt(II) bromide 、 2-萘甲酸 作用下， 以 丙酮 、 叔丁醇 为溶剂， 生成 2-methyl-1-(p-tolyl)-2-vinyltetradecan-1-ol
  参考文献：
  名称：

  Hydrogen Source Tuned Regiodivergent Asymmetric Hydroalkylations of 2‐Substituted 1,3‐Dienes with Aldehydes by Cobalt‐Catalysis

  摘要：

  Catalytic methods allowing for the reliable prediction and control of diverse regioselectivity along with the control of enantioselectivity to access different regio‐ and enantiomers by switching the least reaction parameters are one of the most attractive ways in organic synthesis, which provide access to diverse enantioenriched architectures from identical starting materials. Herein, a Co‐catalyzed regiodivergent and enantioselective reductive hydroalkylation of 1,3‐dienes with aldehydes have been achieved, furnishing different enantioenriched homoallylic alcohol architectures in good levels of enantioselectivity. The reaction features the switch of regioselectivity tuned by the selection of proton source. The use of an acid as proton source provided asymmetric 1,2‐hydroalkylation products under reductive conditions, yet asymmetric 4,3‐hydroalkylation products were obtained with silane as hydride source. This catalytic protocol allows for the access of homoallylic alcohols with two continuous saturated carbon centers in good levels of regio‐, diastereo‐, and enantioselectivity.

  DOI：

  10.1002/anie.202403073
• 作为产物：
  描述：

  1-<1-dodecyl-1-<(trimethylsilyl)methyl>prop-2-enyl>-1H-1,2,3-benzotriazole 反应 8.0h， 以90%的产率得到2-dodecylbuta-1,3-diene
  参考文献：
  名称：

  用于2-烷基取代的1,3-丁二烯的区域特异性合成的四碳单元试剂。

  摘要：

  从被掩盖的丁二烯试剂开始合成2-烷基取代的丁二烯，该掩蔽的丁二烯试剂允许通过锂化并随后与烷基卤化物或脂族醛反应而进行区域特异性合成2-烷基丁二烯。研究了与烯丙基卤化物以及脂族和芳族醛的反应的区域选择性。

  DOI：

  10.1021/jo9818881

文献信息

• A Four-Carbon Unit Reagent for the Regiospecific Synthesis of 2-Alkyl-Substituted 1,3-Butadienes
  作者：Alan R. Katritzky、Larisa Serdyuk、Dorin Toader、Xiaojing Wang

  DOI：10.1021/jo9818881

  日期：1999.3.1

  2-Alkyl-substituted butadienes are synthesized starting from a masked butadiene reagent, which allows the regiospecific synthesis of 2-alkylbutadienes by lithiation and subsequent reaction with alkyl halides or aliphatic aldehydes. The regioselectivity of the reaction with allylic halides and aliphatic and aromatic aldehydes is studied.

  从被掩盖的丁二烯试剂开始合成2-烷基取代的丁二烯，该掩蔽的丁二烯试剂允许通过锂化并随后与烷基卤化物或脂族醛反应而进行区域特异性合成2-烷基丁二烯。研究了与烯丙基卤化物以及脂族和芳族醛的反应的区域选择性。
• Hydrogen Source Tuned Regiodivergent Asymmetric Hydroalkylations of 2‐Substituted 1,3‐Dienes with Aldehydes by Cobalt‐Catalysis
  作者：Xian-Wang Zeng、Jia-Ni Lin、Wei Shu

  DOI：10.1002/anie.202403073

  日期：——

  Catalytic methods allowing for the reliable prediction and control of diverse regioselectivity along with the control of enantioselectivity to access different regio‐ and enantiomers by switching the least reaction parameters are one of the most attractive ways in organic synthesis, which provide access to diverse enantioenriched architectures from identical starting materials. Herein, a Co‐catalyzed regiodivergent and enantioselective reductive hydroalkylation of 1,3‐dienes with aldehydes have been achieved, furnishing different enantioenriched homoallylic alcohol architectures in good levels of enantioselectivity. The reaction features the switch of regioselectivity tuned by the selection of proton source. The use of an acid as proton source provided asymmetric 1,2‐hydroalkylation products under reductive conditions, yet asymmetric 4,3‐hydroalkylation products were obtained with silane as hydride source. This catalytic protocol allows for the access of homoallylic alcohols with two continuous saturated carbon centers in good levels of regio‐, diastereo‐, and enantioselectivity.