(S)-(6-hydroxycyclohex-1-enyl)(naphthalen-2-yl)methanone | 1239710-72-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-(6-hydroxycyclohex-1-enyl)(naphthalen-2-yl)methanone
• 英文别名: [(6S)-6-hydroxycyclohexen-1-yl]-naphthalen-2-ylmethanone
• CAS: 1239710-72-5
• 化学式: C₁₇H₁₆O₂
• 分子量: 252.313
• InChiKey: WIJCGJPDMLVGMY-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 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-naphthalen-2-yl-7-oxohept-5-enal 在 C₂₉H₂₆FeNO₄P 作用下， 以 二氯甲烷 为溶剂， 反应 168.0h， 以72%的产率得到(S)-(6-hydroxycyclohex-1-enyl)(naphthalen-2-yl)methanone
  参考文献：
  名称：

  基于双官能二茂铁的方酰胺-膦作为高对映选择性分子内Morita–Baylis–Hillman反应的有机催化剂†

  摘要：

  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。

  DOI：

  10.1039/c4ob00137k

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。
• 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。
• 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.