2-propylpent-4-en-1-ol | 246530-07-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-propylpent-4-en-1-ol
• CAS: 246530-07-4
• 化学式: C₈H₁₆O
• 分子量: 128.214
• InChiKey: FQNULKBTKGWZAI-UHFFFAOYSA-N

物化性质

• 沸点：
  185.9±9.0 °C(Predicted)
• 密度：
  0.834±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  9
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-propylpent-4-en-1-ol 在 吡啶 、 正丁基锂 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 sodium iodide 作用下， 以 氯仿 为溶剂， 反应 1.5h， 生成 Trimethyl-((Z)-2-propyl-penta-2,4-dienyl)-silane
  参考文献：
  名称：

  Highly selective trapping of unsymmetrical pentadienyl anions by silicon and tin electrophiles. Marked contrast between kinetic and thermodynamic control of product composition

  摘要：

  The nucleophilic reaction of lithium and potassium salts of five pentadienyl anions bearing sterically and/or coordinatively different groups at their unsymmetrical 2-position toward Me3SiCl and Me3SnBr is described. When the anion of the potassium salt was trapped by Me3SiCl, (Z)-4-substituted-pentadienylsilanes were obtained with high selectivity (87-100%). The lithium salt, however, gave a mixture of (E)- and (Z)-4-substituted-pentadienylsilanes. The coupling reaction proceeds under kinetic control, because the product composition from Si trapping reflected the structure of the parent dienyl anion and the steric interaction between the incoming Me3Si group and the substituent on the anion. In contrast, when the anion was trapped by Me3SnBr under the identical conditions, (Z)-2-substituted-pentadienyltins were formed with 60-96% selectivity. Only relatively small changes in product composition, as a function of the cation or the substituent on the anion, were observed. These results could be explained by thermodynamic controlling factors, including a 1,5-Me3Sn shift, and a redistribution of pentadienyl groups under basic conditions.

  DOI：

  10.1021/jo00006a011
• 作为产物：
  描述：

  戊酸甲酯 在 lithium aluminium tetrahydride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 生成 2-propylpent-4-en-1-ol
  参考文献：
  名称：

  Highly selective trapping of unsymmetrical pentadienyl anions by silicon and tin electrophiles. Marked contrast between kinetic and thermodynamic control of product composition

  摘要：

  The nucleophilic reaction of lithium and potassium salts of five pentadienyl anions bearing sterically and/or coordinatively different groups at their unsymmetrical 2-position toward Me3SiCl and Me3SnBr is described. When the anion of the potassium salt was trapped by Me3SiCl, (Z)-4-substituted-pentadienylsilanes were obtained with high selectivity (87-100%). The lithium salt, however, gave a mixture of (E)- and (Z)-4-substituted-pentadienylsilanes. The coupling reaction proceeds under kinetic control, because the product composition from Si trapping reflected the structure of the parent dienyl anion and the steric interaction between the incoming Me3Si group and the substituent on the anion. In contrast, when the anion was trapped by Me3SnBr under the identical conditions, (Z)-2-substituted-pentadienyltins were formed with 60-96% selectivity. Only relatively small changes in product composition, as a function of the cation or the substituent on the anion, were observed. These results could be explained by thermodynamic controlling factors, including a 1,5-Me3Sn shift, and a redistribution of pentadienyl groups under basic conditions.

  DOI：

  10.1021/jo00006a011

文献信息

• PROCESSES FOR THE SYNTHESIS OF CHIRAL 1-ALKANOLS
  申请人：PURDUE RESEARCH FOUNDATION

  公开号：US20160332940A1

  公开（公告）日：2016-11-17

  The invention relates to highly enantioselective processes for the synthesis of chiral 1-alkanols via Zr-catalyzed asymmetric carboalumination of alkenes.

  这项发明涉及通过Zr催化的不对称烯烃碳硼烷化反应合成手性1-烷醇的高对映选择性过程。
• NHC-Catalyzed Ring Expansion of Oxacycloalkane-2-carboxaldehydes: A Versatile Synthesis of Lactones
  作者：Li Wang、Karen Thai、Michel Gravel

  DOI：10.1021/ol8029005

  日期：2009.2.19

  Imidazolinium-derived carbenes catalyze the ring-expansion lactonization of oxacycloalkane-2-carboxaldehydes. A variety of functionalized five-, six-, and seven-membered lactones can be formed efficiently under mild reaction conditions. The success of this new method for the construction of lactones is highly influenced by the electronic nature of the carbene catalyst.

  咪唑啉鎓衍生的卡宾催化氧杂环烷-2-甲醛的扩环内酯化反应。在温和的反应条件下，可以有效地形成各种功能化的五元，六元和七元内酯。卡宾催化剂的电子性质极大地影响了这种构建内酯的新方法的成功。
• Indium-mediated regioselective allylation of terminal epoxides: a facile synthesis of bishomoallyl alcohols
  作者：J.S Yadav、S Anjaneyulu、Md Moinuddin Ahmed、B.V Subba Reddy

  DOI：10.1016/s0040-4039(01)00112-5

  日期：2001.3

  indium, prepared from allyl bromide and indium metal in THF, reacts with terminal epoxides at room temperature to afford the corresponding bishomoallyl alcohols in excellent yields and with good regioselectivity.

  由烯丙基溴和铟金属在THF中制得的烯丙基铟在室温下与末端环氧化物反应，以优异的收率和良好的区域选择性提供相应的双商品烯丙基醇。
• LiAlH4-Induced Reductive Dephosphonylation of α,α-Dialkyl Triethyl β-Phosphonyl Esters: Mechanistic Study and Synthetic Application
  作者：Jia-Liang Zhu、Jr-Sheng Bau、You-Cheng Shih

  DOI：10.1055/s-0031-1290485

  日期：2012.4

  Treatment of α,α-dialkyl triethyl β-phosphonyl esters with LiAlH 4 in CH 2 Cl 2 –THF caused the one-pot dephosphonylation and reduction to yield the corresponding primary alcohols bearing a controllable β secondary carbon center. Mechanistic study has revealed that the LiAlH 4 -induced dephosphonylation should occur first with the assistance of the carboxylate group, and the hydrogen source of the

  在 CH 2 Cl 2 –THF 中用 LiAlH 4 处理 α,α-二烷基三乙基 β-膦酰基酯引起一锅脱膦酰基化和还原反应，产生带有可控 β 仲碳中心的相应伯醇。机理研究表明，LiAlH 4 诱导的脱膦酰化应首先在羧酸根的帮助下发生，所得新 C-H 键的氢源是 LiAlH 4 。
• Processes for the synthesis of chiral 1-alkanols
  申请人：PURDUE RESEARCH FOUNDATION

  公开号：US10000432B2

  公开（公告）日：2018-06-19

  The invention relates to highly enantioselective processes for the synthesis of chiral 1-alkanols via Zr-catalyzed asymmetric carboalumination of alkenes.

  本发明涉及通过 Zr 催化的烯烃不对称羧氨化合成手性 1-烷醇的高对映选择性工艺。