3-Methyl-2-phenyl-3-buten-1-ol | 57502-36-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-Methyl-2-phenyl-3-buten-1-ol
• 英文别名: 3-methyl-2-phenylbut-3-en-1-ol
• CAS: 57502-36-0
• 化学式: C₁₁H₁₄O
• 分子量: 162.232
• InChiKey: YDNITLGPLSXQAS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  3-Methyl-2-phenyl-3-buten-1-ol 在 三氟化硼乙醚 、 N-亚硫酰基-p-甲苯磺胺 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 12.0h， 生成 4-Methylidene-5-phenyloxathiane 2,2-dioxide
  参考文献：
  名称：

  Convenient Syntheses of Chiral Cyclic Sulfinates (Sultines) from Unsaturated Alcohols

  摘要：

  The reaction of unsaturated alcohols with N-sulfinyl-p-toluenesulfonamide (TsNSO) is shown to lead stereoselectively to chiral cyclic or bicyclic sulfinates (sultines). The reactions occur at ambient temperatures and afford a general route to delta- and epsilon-sultines which are notable for their crystallinity and thermal stability. These studies confirm the preservation of stereochemical integrity of the carbon atom alpha to the oxygen atom in the sultine ring. Some unsaturated aldehydes furnish sultines via a tandem oxo-ene cyclization and subsequent ring closure to the sultine. In some reactions, N-toluenesulfonamide derivatives of sultines (compounds of type 11) were isolated, and since those were converted into the sultines by the action of BF3-OEt(2), such sulfonamides are considered to be intermediates in the reaction pathway.

  DOI：

  10.1021/jo00129a056
• 作为产物：
  描述：

  1-溴-3-甲基丁-3-烯-2-醇 在 氢氧化钾 、 magnesium 作用下， 反应 1.5h， 生成 3-Methyl-2-phenyl-3-buten-1-ol
  参考文献：
  名称：

  Synthesis and some reactions of isopropenyloxirane

  摘要：

  DOI：

  10.1007/bf00504391

文献信息

• Regioselective Arylboration of Isoprene and Its Derivatives by Pd/Cu Cooperative Catalysis
  作者：Kevin B. Smith、M. Kevin Brown

  DOI：10.1021/jacs.7b04024

  日期：2017.6.14

  A method for the regioselective arylboration of isoprene and its derivatives is presented. These reactions allow for the synthesis of useful building blocks from simple components. Through these studies, an unusual additive effect with DMAP has been uncovered that allows for altered reactivity and the formation of quaternary carbon centers. The utility of this method is demonstrated toward the formal

  提出了异戊二烯及其衍生物的区域选择性芳基硼化的方法。这些反应允许从简单的组分合成有用的构建块。通过这些研究，发现了 DMAP 的一种不寻常的累加效应，它可以改变反应性并形成四元碳中心。这种方法的效用被证明对 mesembrine 的正式合成。
• 1-(<i>N,N</i>-Diisopropylcarbamoyloxy)-1-tosyl-1-alkenes—<i>a</i>²<i>d</i>¹ Synthons via Tandem Umpolung
  作者：Yue-Lei Chen、Dieter Hoppe

  DOI：10.1021/jo900347s

  日期：2009.6.5

  have been developed as an a2d1 synthon via tandem umpolung. Upon addition of Grignard reagents and further quench by carbonyl compounds, this synthon produces α,α′-branched-α′-oxygenated ketones. Strategically, this widely applicable method installs respectively a carbanion unit and a carbonyl unit formally onto the α-carbon and the carbonyl center of an aldehyde in one-pot.

  1-（N，N- -Diisopropylcarbamoyloxy）-1-甲苯磺酰基烯烃已经被开发作为一个2 d 1点通过串联极性转换的合成子。在添加格利雅试剂和羰基化合物进一步骤冷的，这种合成子产生α，α ' -支化-α ' -oxygenated酮。从战略上讲，这种广泛应用的方法是在一个罐中分别将碳负离子单元和羰基单元分别正式安装在醛的α-碳和羰基中心上。
• Cu-Catalyzed Enantioselective Protoboration of 2,3-Disubstituted 1,3-Dienes
  作者：Sensheng Liu、Yangbin Liu、Arthur Flaget、Cheng Zhang、Clément Mazet

  DOI：10.1021/acs.orglett.3c02627

  日期：2023.9.22

  A Cu-catalyzed regio- and enantioselective protoboration of 2,3-disubstituted 1,3-dienes is described. The protocol operates under mild conditions and is applicable to symmetrically and unsymmetrically substituted dienes, providing access to homoallylic boronates in consistently high yield, regioselectivity, and enantiomeric ratio. Preliminary investigations point to a complex mechanism.

  描述了 2,3-二取代 1,3-二烯的 Cu 催化区域选择性和对映选择性原硼化反应。该方案在温和条件下运行，适用于对称和不对称取代的二烯，以一致的高产率、区域选择性和对映体比例提供同烯丙基硼酸酯。初步调查表明存在一个复杂的机制。
• Stereoselective Pinacol-Type Rearrangement of 2,3-Epoxy Alcohols with Retention of Configuration Mediated by Bis(iodozincio)methane
  作者：Seijiro Matsubara、Hiromasa Yamamoto、Koichiro Oshima

  DOI：10.1002/1521-3773(20020802)41:15<2837::aid-anie2837>3.0.co;2-x

  日期：2002.8.2
• GEVORKYAN, A. A.;KAZARYAN, P. I.;AVAKYAN, S. V., XIMIYA GETEROTSIKL. SOEDIN., 1985, N 4, 450-457
  作者：GEVORKYAN, A. A.、KAZARYAN, P. I.、AVAKYAN, S. V.

  DOI：——

  日期：——