(±)-2-methyl-1-(thiophen-2-yl)prop-2-en-1-ol | 1245792-94-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: (±)-2-methyl-1-(thiophen-2-yl)prop-2-en-1-ol
• 英文别名: 1-(2-thienyl)-2-methylprop-2-en-1-ol；2-Methyl-1-thiophen-2-ylprop-2-en-1-ol；2-methyl-1-thiophen-2-ylprop-2-en-1-ol
• CAS: 1245792-94-2
• 化学式: C₈H₁₀OS
• 分子量: 154.233
• InChiKey: JEDNPTAFIRKYDY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  48.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (±)-2-methyl-1-(thiophen-2-yl)prop-2-en-1-ol 、 2-iodobenzyl methanesulfonate 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 18.0h， 以79%的产率得到(±)-2-(1-((2-iodobenzyl)oxy)-2-methylallyl)thiophene
  参考文献：
  名称：

  Functionalized Chromans and Isochromans via a Diastereoselective Pd(0)-Catalyzed Carboiodination

  摘要：

  A diastereoselective approach to isochromans and chromans via Pd(0)-catalyzed carboiodination is reported. The transformations using this methodology display excellent yields and diastereoselectivities as well as broad functional group compatibility. The selectivity observed in these cyclizations, forming isochroman or chroman targets, is postulated to originate from the minimization of A(1,2) strain and axial axial interactions, respectively. This method has also been used to highlight the concept of reversible oxidative addition to carbon iodine bonds in polyiodinated substrates.

  DOI：

  10.1021/ol302111y
• 作为产物：
  描述：

  1-(2-噻吩基)-1-丙酮 在 sodium tetrahydroborate 、 cerium(III) chloride heptahydrate 、 乙酸酐 作用下， 以 甲醇 为溶剂， 反应 5.0h， 生成 (±)-2-methyl-1-(thiophen-2-yl)prop-2-en-1-ol
  参考文献：
  名称：

  Fc-PIP催化的芳基烯基甲醇的动力学拆分

  摘要：

  开发了有效的动力学拆分非芳基酰基转移催化剂Fc-PIP催化的各种芳基烯基羰基醇的方法，可提供相应的未反应的醇，其ee值高达99％，优良的ee值高达24。

  DOI：

  10.1002/cjoc.201200410

文献信息

• Rhodium-Catalyzed Synthesis of γ-Pyrones by Three Consecutive Redox-Aldol Reactions of Allylic Alcohols with α,β-Unsaturated Aldehydes
  作者：Akio Mizuno、Hiroyuki Kusama、Nobuharu Iwasawa

  DOI：10.1002/chem.201001068

  日期：——

  All together now! A unique RhI‐catalyzed reaction was developed to produce γ‐pyrones, which are 1,3,5‐triketone equivalents. This reaction was thought to proceed by three redox reactions of allylic alcohols, two intermolecular aldol reactions of α,β‐unsaturated aldehydes, and one intramolecular aldol reaction to afford 1,3‐cyclohexanediones, which were then converted into γ‐pyrones (see scheme; TMSOTf=trimethylsilyl

  现在都在一起了！开发了独特的Rh I催化反应以生成γ-吡喃酮，其为1,3,5-三酮当量。该反应被认为是通过烯丙醇的三个氧化还原反应，两个α，β-不饱和醛的分子间羟醛反应和一个分子内的羟醛反应进行的，以提供1,3-环己二酮，然后将其转化为γ-吡喃酮（见方案） ； TMSOTf ＝三甲基甲硅烷基三氟甲磺酸盐）。
• One-Pot and Unsymmetrical Bis-Allylation of Malononitrile with Conjugated Dienes and Allylic Alcohols
  作者：Wenxiu Gao、Dong Zhang、Xiaoyu Zhang、Xinying Cai、Peizhong Xie、Teck-Peng Loh

  DOI：10.1021/acs.orglett.2c03405

  日期：2022.12.30

  A Pd/Ca catalytic system to promote the unsymmetrical bis-allylation of malononitrile was developed by selecting conjugated dienes and allylic alcohols as allylic reagents. This catalytic system suppressed the competitive symmetrical bis-allylation process and guaranteed the desired unsymmetrical bis-allylation with high chemoselectivity. A wide range of conjugated dienes and allylic alcohols were

  通过选择共轭二烯和烯丙醇作为烯丙基试剂，开发了促进丙二腈不对称双烯丙基化的 Pd/Ca 催化体系。该催化体系抑制了竞争性对称双烯丙基化过程，并保证了所需的具有高化学选择性的不对称双烯丙基化。在这种转化中，广泛的共轭二烯和烯丙醇具有良好的耐受性，并且高效地获得了多种 1,6-二烯。
• Functionalized Chromans and Isochromans via a Diastereoselective Pd(0)-Catalyzed Carboiodination
  作者：David A. Petrone、Hasnain A. Malik、Antonin Clemenceau、Mark Lautens

  DOI：10.1021/ol302111y

  日期：2012.9.21

  A diastereoselective approach to isochromans and chromans via Pd(0)-catalyzed carboiodination is reported. The transformations using this methodology display excellent yields and diastereoselectivities as well as broad functional group compatibility. The selectivity observed in these cyclizations, forming isochroman or chroman targets, is postulated to originate from the minimization of A(1,2) strain and axial axial interactions, respectively. This method has also been used to highlight the concept of reversible oxidative addition to carbon iodine bonds in polyiodinated substrates.
• Kinetic Resolution of Aryl Alkenylcarbinols Catalyzed by Fc-PIP
  作者：Bin Hu、Meng Meng、Shanshan Jiang、Weiping Deng

  DOI：10.1002/cjoc.201200410

  日期：2012.6

  An effective kinetic resolution of a variety of aryl alkenylcarbinols catalyzed by nonenzymatic acyl transfer catalyst Fc‐PIP was developed, affording corresponding unreacted alcohols in good to excellent ee value up to 99% and with selectivity factors up to 24.

  开发了有效的动力学拆分非芳基酰基转移催化剂Fc-PIP催化的各种芳基烯基羰基醇的方法，可提供相应的未反应的醇，其ee值高达99％，优良的ee值高达24。