(S)-(4-fluorophenyl)(6-hydroxycyclohex-1-enyl)methanone | 1239710-71-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (S)-(4-fluorophenyl)(6-hydroxycyclohex-1-enyl)methanone
• 英文别名: (4-fluorophenyl)-[(6S)-6-hydroxycyclohexen-1-yl]methanone
• CAS: 1239710-71-4
• 化学式: C₁₃H₁₃FO₂
• 分子量: 220.243
• InChiKey: BKHFPJRHPWOXCV-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  7-(4-fluorophenyl)-7-oxohept-5-enal 在 3-[[(1R,2R)-2-diphenylphosphanylcyclohexyl]amino]-4-ethoxycyclobut-3-ene-1,2-dione 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以96%的产率得到(S)-(4-fluorophenyl)(6-hydroxycyclohex-1-enyl)methanone
  参考文献：
  名称：

  手性膦-方酸酰胺作为分子内Morita-Baylis-Hillman反应的对映选择性催化剂。

  摘要：

  新型的含叔膦的方酰胺被开发为手性双官能有机催化剂，以促进ω-甲酰基-烯酮的不对称分子内Morita-Baylis-Hillman反应。加合物以良好的对映选择性（高达93％ee）以高收率获得。

  DOI：

  10.1039/c0cc03187a

文献信息

• Bifunctional ferrocene-based squaramide-phosphine as an organocatalyst for highly enantioselective intramolecular Morita–Baylis–Hillman reaction
  作者：Xiaorui Zhang、Pengfei Ma、Dongxu Zhang、Yang Lei、Shengyong Zhang、Ru Jiang、Weiping Chen

  DOI：10.1039/c4ob00137k

  日期：——

  catalysis, ferrocene could be an excellent scaffold for organocatalysts. The simple and easily accessible bifunctional ferrocene-based squaramide-phosphine shows high enantioselectivity in the intramolecular Morita–Baylis–Hillman reaction of 7-aryl-7-oxo-5-heptenals, giving a variety of 2-aroyl-2-cyclohexenols in up to 96% ee.

  这项工作表明，根据金属催化，二茂铁可能是有机催化剂的优良支架。简单易行的基于双官能二茂铁的方酰胺-膦在7-芳基-7-氧代-5-庚烯的分子内Morita-Baylis-Hillman反应中显示出很高的对映选择性，从而产生了多种2-芳基-2-环己烯醇到96％ee。
• The enantioselective intramolecular Morita–Baylis–Hillman reaction catalyzed by amino acid-derived phosphinothiourea
  作者：Jing-Jing Gong、Kui Yuan、Hong-Liang Song、Xin-Yan Wu

  DOI：10.1016/j.tet.2010.01.085

  日期：2010.3

  A series of chiral bifunctional phosphinothioureas derived from l-amino acids have been developed to promote the enantioselective intramolecular Morita–Baylis–Hillman reaction. The process afforded the cyclic hydroxyl enones with up to 84% ee and good yields under mild conditions.

  已经开发了一系列衍生自l-氨基酸的手性双功能膦硫脲，以促进对映选择性分子内Morita-Baylis-Hillman反应。该方法在温和条件下提供了高达84％ee的环状羟基烯酮和良好的收率。
• Enantioselective intramolecular Morita–Baylis–Hillman reaction using chiral bifunctional phosphinothiourea as an organocatalyst
  作者：Kui Yuan、Hong-Liang Song、Yinjun Hu、Jian-Fei Fang、Xin-Yan Wu

  DOI：10.1016/j.tetasy.2010.04.061

  日期：2010.4

  Chiral cyclohexane-based phosphinothioureas were found to be efficient organocatalysts for the enantioselective intramolecular Morita–Baylis–Hillman reaction of ω-formyl-enone. Among the solvents screened, t-BuOH was the best one which provided good yield and enantioselectivity. Moreover in the presence of 3 mol % of phosphinothiourea 2b, the desired products were obtained in good-to-excellent yields

  发现基于手性环己烷的膦硫脲类化合物是ω-甲酰基-烯酮的对映选择性分子内Morita-Baylis-Hillman反应的有效有机催化剂。在筛选出的溶剂中，叔-BuOH是最好的溶剂，可提供良好的收率和对映选择性。此外，在3mol％的硫代硫脲2b的存在下，在温和的反应条件下以良好至优异的产率和高达98％ee获得所需产物。
• 10.24820/ark.5550190.p011.072dummy2
  作者：Aydin, A. Ebru

  DOI：10.24820/ark.5550190.p011.072dummy2

  日期：——
• Highly Enantioselective Intramolecular Morita-Baylis-Hillman Reaction Catalyzed by Mannose-Based Thiourea-phosphine
  作者：Weihong Yang、Kui Yuan、Hongliang Song、Feng Sha、Xinyan Wu

  DOI：10.1002/cjoc.201500468

  日期：2015.10

  AbstractThe saccharide‐based chiral bifunctional thiourea‐phosphines were developed as chiral organocatalysts for the intramolecular Morita‐Baylis‐Hillman reaction of ω‐formyl‐enones. With only 2 mol% of thiourea‐phosphine catalyst 3c, chiral functionalized cyclohexenes were achieved under mild reaction conditions with excellent yields and enantioselectivities.