6-Chloro-2-(4-methoxy-phenyl)-2H-chromene | 121507-61-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 6-Chloro-2-(4-methoxy-phenyl)-2H-chromene
• 英文别名: 6-chloro-2-(4-methoxyphenyl)-2H-chromene
• CAS: 121507-61-7
• 化学式: C₁₆H₁₃ClO₂
• 分子量: 272.731
• InChiKey: WYHMMUWLTMGLKC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-Chloro-2-(4-methoxy-phenyl)-2H-chromene 在 chloroauric acid 、 水 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以87%的产率得到3-(5-chloro-2-hydroxyphenyl)-1-(4-methoxyphenyl)-propan-1-one
  参考文献：
  名称：

  An unexpected rearrangement-hydration reaction sequence of 2H-chromenes to dihydrochalcones under catalysis of HAuCl4

  摘要：

  2-Aryl-2H-chromenes in aqueous DCM medium under catalysis of HAuCl4 are converted into 3-(2-hydroxyaryl)-1-arylpropan-1-ones through hydration-rearrangement reaction sequence in very good yield. The key step probably involves the [1,5] hydride shift followed by the hydrolysis under the reaction condition. The notable advantages of this method are operational simplicity and ease of isolation of products and also provide a pathway to convert the chalcone into DHCs with the transposition of carbonyl group. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.08.117
• 作为产物：
  描述：

  2-羟基-5-氯苯乙酮 在 sodium tetrahydroborate 、 sodium hydroxide 作用下， 以 乙醇 、 水 、 异丙醇 为溶剂， 生成 6-Chloro-2-(4-methoxy-phenyl)-2H-chromene
  参考文献：
  名称：

  An unexpected rearrangement-hydration reaction sequence of 2H-chromenes to dihydrochalcones under catalysis of HAuCl4

  摘要：

  2-Aryl-2H-chromenes in aqueous DCM medium under catalysis of HAuCl4 are converted into 3-(2-hydroxyaryl)-1-arylpropan-1-ones through hydration-rearrangement reaction sequence in very good yield. The key step probably involves the [1,5] hydride shift followed by the hydrolysis under the reaction condition. The notable advantages of this method are operational simplicity and ease of isolation of products and also provide a pathway to convert the chalcone into DHCs with the transposition of carbonyl group. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.08.117

文献信息

• Homodimerization of 2<i>H</i>-chromenes catalyzed by Brønsted-acid derived UiO-66 MOFs
  作者：Zongcheng Miao、Zihao Zhou、Houliang Tang、Mengdie Yu、Daniele Ramella、Xin Du、Yi Luan

  DOI：10.1039/c7cy02362f

  日期：——

  Brønsted acid UiO-66 MOFs were prepared for the efficient homo-dimerization of 2H-chromenes, which involves a tandem rearrangement/hetero-Diels–Alder reaction sequence.

  Brønsted酸UiO-66 MOFs被制备用于高效的2H-色酮的同源二聚化，其中涉及串联重排/杂环Diels-Alder反应序列。
• A facile 2<i>H</i>-chromene dimerization through an <i>ortho</i>-quinone methide intermediate catalyzed by a sulfonyl derived MIL-101 MOF
  作者：Xin Du、Xiujuan Li、Houliang Tang、Wenyu Wang、Daniele Ramella、Yi Luan

  DOI：10.1039/c8nj01354c

  日期：——

  SEM, XRD, FTIR, BET and TGA. An efficient and diastereoselective homo-dimerization of 2H-chromenes catalysis was achieved using the sulfonyl derived MIL-101 MOF as a catalyst. A benzopyranobenzopyran polycyclic structure was generated in high yield and diastereoselectivity under mild catalytic reaction conditions. Furthermore, a regio-isomer was observed when 2H-chromene bears different substitution

  MIL-101–SO 3 H MOF是使用市售材料合成的。合成后的MIL-101-SO 3 H的特征在于SEM，XRD，FTIR，BET和TGA。使用磺酰基衍生的MIL-101 MOF作为催化剂，可实现2 H-苯甲基二烯催化的高效非对映选择性均二聚。在温和的催化反应条件下，以高收率和非对映选择性生成了苯并吡喃并苯并吡喃多环结构。此外，当2 H-色烯带有不同的取代基时，观察到一个区域异构体，从而提供了chromeno [2,3- b] chromene二聚体，收率高，非对映选择性好。提出了一种具有串联重排/杂-Diels-Alder反应序列的机制，这得到了证据的支持。此外，酸性MIL-101 MOF催化剂可以循环使用十次，而不会影响收率和选择性。
• A novel synthesis of flav-3-enes by claisen rearrangement
  作者：Rajaram Sankara Subramanian、Kalpattu Kuppusamy Balasubramanian

  DOI：10.1016/s0040-4039(00)82458-2

  日期：——

  1-Arylprop-2-ynyl aryl ethers () undergo a facile Claisen rearrangement in N,N-diethylaniline/o-dichlorobenzene to give flav-3-enes in good yields.

  1-芳基丙-2-炔基芳基醚（）在N，N-二乙基苯胺/邻二氯苯中进行容易的Claisen重排，从而以高收率得到黄三烯。
• Subramanian, R. Sankara; Balasubramanian, K. K., Synthetic Communications, 1989, vol. 19, # 7,8, p. 1255 - 1260
  作者：Subramanian, R. Sankara、Balasubramanian, K. K.

  DOI：——

  日期：——
• SUBRAMANIAN, RAJARAM SANKARA;BALASUBRAMANIAN, KALPATTU KUPPUSAMY, TETRAHEDRON. LETT., 29,(1988) N 51, C. 6797-6800
  作者：SUBRAMANIAN, RAJARAM SANKARA、BALASUBRAMANIAN, KALPATTU KUPPUSAMY

  DOI：——

  日期：——