(R)-(6-hydroxycyclohex-1-enyl)(o-tolyl)methanone | 865363-33-3

• 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: (R)-(6-hydroxycyclohex-1-enyl)(o-tolyl)methanone
• 英文别名: [(6R)-6-hydroxycyclohexen-1-yl]-(2-methylphenyl)methanone
• CAS: 865363-33-3
• 化学式: C₁₄H₁₆O₂
• 分子量: 216.28
• InChiKey: ZORRFISOEOWDMM-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  7-(2-methylphenyl)-7-oxohept-5-enal 在 (S)-1-(3,5-bis(trifluoromethyl)phenyl)-3-(1-(diphenylphosphino)-3-phenylpropan-2-yl)thiourea 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 (R)-(6-hydroxycyclohex-1-enyl)(o-tolyl)methanone 、 (S)-(6-hydroxycyclohex-1-enyl)(o-tolyl)methanone
  参考文献：
  名称：

  氨基酸衍生的硫代硫脲催化的对映选择性分子内Morita-Baylis-Hillman反应

  摘要：

  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。

  DOI：

  10.1016/j.tet.2010.01.085

文献信息

• Chiral phosphine-squaramides as enantioselective catalysts for the intramolecular Morita–Baylis–Hillman reaction
  作者：Hong-Liang Song、Kui Yuan、Xin-Yan Wu

  DOI：10.1039/c0cc03187a

  日期：——

  squaramides containing tertiary phosphine were developed as chiral bifunctional organic catalysts to promote the asymmetric intramolecular Morita-Baylis-Hillman reaction of omega-formyl-enones. The adducts were obtained in high yields with good-to-excellent enantioselectivity (up to 93% ee).

  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。
• 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：——
• Chiral thiourea derivatives as organocatalyts in the enantioselective Morita-Baylis-Hillman reactions
  作者：A. Ebru Aydin

  DOI：10.24820/ark.5550190.p011.072

  日期：——

  Novel chiral bifunctional thiourea derivatives have been synthesised and successfully applied to the intermolecular Morita-Baylis-Hillman (MBH) reaction of an aromatic aldehyde with methyl vinyl ketone (MVK) and to the intramolecular MBH reaction of omega-formyl-enone. The corresponding products were obtained with high enantioselectivities (up to 98 % ee). The thiourea organocatalyst derived from a B-amino alcohol gave high enantioselectivities (92 % ee) in the intermolecular MBH reaction, whereas the same chiral ligand afforded the corresponding product in high yield (85 %) with moderate enantioselectivity (75 % ee) in the intramolecular MBH reaction. The use of a thiophene ring-containing thiourea derivative gave high enantioselectivities in the intermolecular and intramolecular MBH reactions (85 % and 95 % ee, respectively).[GRAPHICS].