Di-sec.-2-butenyl-carbinol | 61005-41-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Di-sec.-2-butenyl-carbinol
• 英文别名: 3,5-dimethyl-hepta-2,5-dien-4-ol；3,5-Dimethylhepta-2,5-dien-4-ol
• CAS: 61005-41-2
• 化学式: C₉H₁₆O
• 分子量: 140.225
• InChiKey: OIKRAIPRESLNRF-UHFFFAOYSA-N

物化性质

• 沸点：
  56.3 °C(Press: 1.5 Torr)
• 密度：
  0.866±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.56
• 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：

  Di-sec.-2-butenyl-carbinol 在 manganese(IV) oxide 、 甲酸 、 磷酸 作用下， 以 正戊烷 为溶剂， 反应 2.0h， 生成 1,2,3,4,5-五甲基环戊二烯
  参考文献：
  名称：

  Communications- Preparation of 1,2,3,4,5-Pentamethyl-cyclopentadiene, 1,2,3,4,5,5-Hexamethyl-cyclopentadiene, and 1,2,3,4,5-Pentamethyl-cyclopentadienylcarbinol

  摘要：

  DOI：

  10.1021/jo01080a623
• 作为产物：
  描述：

  2-溴-2-丁烯 、 甲酸乙酯 在 lithium 作用下， 以 乙醚 为溶剂， 生成 Di-sec.-2-butenyl-carbinol
  参考文献：
  名称：

  Enzymelike Catalysis of the Nazarov Cyclization by Supramolecular Encapsulation

  摘要：

  The water-soluble, self-assembled, tetrahedral assembly K12Ga4L6 (L = 1,5-biscatecholamidenaphthalene) catalyzes the Nazarov cyclization of 1,3-pentadienols with extremely high levels of efficiency. The catalyzed reaction proceeds over a million times faster than the background reaction, an increase comparable to those observed in some enzymatic systems. This catalysis operates under aqueous conditions at mild temperatures and pH, and the reaction is halted by the addition of an appropriate inhibitor. This unprecedented rate enhancement is attributed to both the stabilization of protonated reaction intermediates and the effect of constrictive binding on the bound guest.

  DOI：

  10.1021/ja102633e

文献信息

• Site‐ and Enantioselective Iridium‐Catalyzed Desymmetric Mono‐Hydrogenation of 1,4‐Dienes
  作者：Haibo Wu、Hao Su、Erik J. Schulze、Bram B. C. Peters、Mark D. Nolan、Jianping Yang、Thishana Singh、Mårten S. G. Ahlquist、Pher G. Andersson

  DOI：10.1002/anie.202107267

  日期：2021.8.23

  The control of site selectivity in asymmetric mono-hydrogenation of dienes or polyenes remains largely underdeveloped. Herein, we present a highly efficient desymmetrization of 1,4-dienes via iridium-catalyzed site- and enantioselective hydrogenation. This methodology demonstrates the first iridium-catalyzed hydrogenative desymmetriation of meso dienes and provides a concise approach to the installation

  二烯或多烯不对称单氢化中位点选择性的控制在很大程度上仍然不发达。在此，我们提出了一种通过铱催化的位点和对映选择性氢化对 1,4-二烯进行高效去对称化的方法。该方法展示了第一个铱催化的内消旋二烯的氢化去对称作用，并提供了一种在烯烃附近安装两个邻位立构中心的简明方法。一系列二乙烯基甲醇和二乙烯基碳酰胺底物获得了高分离产率（高达 96%）和优异的非对映选择性和对映选择性（高达 99:1 dr 和 99% ee）。DFT 计算表明，羟基氧和反应氢化物之间的相互作用是二乙烯基甲醇去对称化的立体选择性的原因。根据计算的能量分布，应用模拟产品随时间分布的模型来显示该过程的直观动力学。通过天然产物萨拉戈酸A和(+)-invictolide的关键中间体的合成证明了该方法的有效性。
• Enzymelike Catalysis of the Nazarov Cyclization by Supramolecular Encapsulation
  作者：Courtney J. Hastings、Michael D. Pluth、Robert G. Bergman、Kenneth N. Raymond

  DOI：10.1021/ja102633e

  日期：2010.5.26

  The water-soluble, self-assembled, tetrahedral assembly K12Ga4L6 (L = 1,5-biscatecholamidenaphthalene) catalyzes the Nazarov cyclization of 1,3-pentadienols with extremely high levels of efficiency. The catalyzed reaction proceeds over a million times faster than the background reaction, an increase comparable to those observed in some enzymatic systems. This catalysis operates under aqueous conditions at mild temperatures and pH, and the reaction is halted by the addition of an appropriate inhibitor. This unprecedented rate enhancement is attributed to both the stabilization of protonated reaction intermediates and the effect of constrictive binding on the bound guest.
• Communications- Preparation of 1,2,3,4,5-Pentamethyl-cyclopentadiene, 1,2,3,4,5,5-Hexamethyl-cyclopentadiene, and 1,2,3,4,5-Pentamethyl-cyclopentadienylcarbinol
  作者：L deVries

  DOI：10.1021/jo01080a623

  日期：1960.10