4-(4-chlorophenyl)-2-phenyl-3,6-dihydro-2H-pyran | 1367736-99-9

• 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: 4-(4-chlorophenyl)-2-phenyl-3,6-dihydro-2H-pyran
• CAS: 1367736-99-9
• 化学式: C₁₇H₁₅ClO
• 分子量: 270.758
• InChiKey: LQTDSBFGOWRCTL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-(buta-1,3-dien-2-yl)-4-chlorobenzene 、 苯甲醛 在 aluminum (III) chloride 作用下， 以 四氯化碳 为溶剂， 反应 15.0h， 以73%的产率得到4-(4-chlorophenyl)-2-phenyl-3,6-dihydro-2H-pyran
  参考文献：
  名称：

  AlCl 3催化芳香醛与简单二烯的oxa-Diels-Alder反应

  摘要：

  已经开发了由AlCl 3催化的高度区域选择性和非对映选择性的oxa-Diels-Alder反应。该反应是有效的并且以良好的官能团相容性为特征，可以容忍F，Cl，CN，NO 2，OMe和硫代苯基。基于该结果，提出了路易斯酸催化的协同环加成机理。

  DOI：

  10.1016/j.tet.2016.10.049

文献信息

• Iron Corrole-catalyzed [4 + 2] Cycloaddition of Dienes and Aldehydes
  作者：Toru Kuwano、Takuya Kurahashi、Seijiro Matsubara

  DOI：10.1246/cl.130672

  日期：2013.10.5

  We have developed cationic iron(IV) corrole-catalyzed formal hetero-Diels–Alder reaction of aldehydes with dienes, which opens the way for divergent synthesis of pyrans. The potential utility of the catalyst was also demonstrated by carrying out cycloaddition of α,β-unsaturated aldehyde with a diene to give pyran selectively. Furthermore, the catalytic reactivity of iron corrole complex on the cycloaddition was determined by comparing that of iron porphyrin complex.

  我们开发了一种阳离子铁(IV) corrole 催化的醛与二烯的正式杂-Diels-Alder 反应，这为吡喃的多样性合成开辟了道路。催化剂的潜在应用价值也通过 α,β-不饱和醛与二烯的环加成反应得到选择性吡喃的生成得以证明。此外，通过比较铁 porphyrin 配合体在环加成反应中的催化活性，确定了铁 corrole 配合体的催化反应活性。
• Efficient Synthesis of 3,6‐Dihydro‐2H‐pyrans via [3+2+1] Annulation Based on the Heteroatom‐free Tri‐atom Donor
  作者：Hui Li、Haiping Liu、Yufeng Liu、Zhongzhong Cao、Miaodong Su、Meiqiang Fu、Weiping Luo、Qiang Liu、Cancheng Guo

  DOI：10.1002/adsc.201900900

  日期：2019.12.3

  strategy based on the heteroatom‐free tri‐atom donor to synthesize 3,6‐dihydro‐2H‐pyrans has been developed. In this method, 2‐arylpropylene served as tri‐atom donor to contribute three carbon atoms, the heteroatom was provided by aldehyde, and DMSO served as one carbon donor and solvent. This annulation reaction gave 3,6‐dihydro‐2H‐pyrans in moderate to good yields. Based on the control experiments, a

  基于无杂原子的三原子供体合成3,6-二氢-2 H-吡喃的新的[3 + 2 + 1]环空策略已被开发出来。在这种方法中，2-芳基丙烯充当三原子供体，贡献三个碳原子，杂原子由醛提供，而DMSO作为一种碳供体和溶剂。此成环反应产生3,6-dihydro-2 H-吡喃，产率中等至良好。在控制实验的基础上，提出了一种可能的机理。
• Cationic Iron(III) Porphyrin-Catalyzed [4 + 2] Cycloaddition of Unactivated Aldehydes with Simple Dienes
  作者：Kyohei Fujiwara、Takuya Kurahashi、Seijiro Matsubara

  DOI：10.1021/ja300790x

  日期：2012.3.28

  Cationic iron(III) porphyrin was found to be an efficient catalyst for the highly chemoselective hetero-Diels Alder-type reaction of aldehydes with 1,3-dienes. The catalyzed process did not require the use of electron-deficient aldehydes such as glyoxylic acid derivatives or activated electron-rich 1,3-dienes such as Danishefslcy's diene and Rawal's diene. The high functional group tolerance and robustness of the catalyst were demonstrated. Further, the potential utility of the catalyst was demonstrated by performing the cycloaddition in the presence of water and by carrying out cycloaddition of an unactivated ketone such as cyclohexanone with a diene.
• AlCl3 catalyzed oxa-Diels-Alder reaction of aromatic aldehydes with simple dienes
  作者：Wujun Jian、Bo Qian、Hongli Bao、Daliang Li

  DOI：10.1016/j.tet.2016.10.049

  日期：2017.7

  A highly regioselective and diastereoselective oxa-Diels-Alder reaction catalyzed by AlCl3 has been developed. This reaction is efficient and characterized by good functional group compatibility, F, Cl, CN, NO2, OMe and thiophenyl groups are tolerated. A Lewis acid catalyzed concerted cycloaddition mechanism is proposed based on the results.

  已经开发了由AlCl 3催化的高度区域选择性和非对映选择性的oxa-Diels-Alder反应。该反应是有效的并且以良好的官能团相容性为特征，可以容忍F，Cl，CN，NO 2，OMe和硫代苯基。基于该结果，提出了路易斯酸催化的协同环加成机理。