3-(Benzo[d][1,3]dioxol-5-yl)-1-(naphthalen-2-yl)prop-2-en-1-one | 52601-57-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 3-(Benzo[d][1,3]dioxol-5-yl)-1-(naphthalen-2-yl)prop-2-en-1-one
• 英文别名: 3-(1,3-benzodioxol-5-yl)-1-naphthalen-2-ylprop-2-en-1-one
• CAS: 52601-57-7
• 化学式: C₂₀H₁₄O₃
• 分子量: 302.329
• InChiKey: UIASZIZNIOGSLS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(cinnamylsulfonyl)-4-methylbenzene 、 3-(Benzo[d][1,3]dioxol-5-yl)-1-(naphthalen-2-yl)prop-2-en-1-one 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以75%的产率得到5-(5-Naphthalen-2-yl-2-phenylphenyl)-1,3-benzodioxole
  参考文献：
  名称：

  多取代quaterphenyls和环丙烷的一锅法合成

  摘要：

  朝向多官能化quaterphenyls一种有效的一步合成路线3或环丙烷4选自取代的查耳酮开发1和砜2以良好的收率通过区域选择性[3C + 3C]或[1C + 2C]环。该反应具有温和的条件，多取代和对官能团的耐受性，并且不含过渡金属催化剂。该方案为合成四苯基或环丙烷的常规方法提供了一种新颖的替代方法。

  DOI：

  10.1016/j.tet.2013.09.060
• 作为产物：
  描述：

  胡椒醛 、 2-萘乙酮 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 生成 3-(Benzo[d][1,3]dioxol-5-yl)-1-(naphthalen-2-yl)prop-2-en-1-one
  参考文献：
  名称：

  多官能化的一锅法合成米-terphenyls

  摘要：

  朝向多官能化一种简便一步法合成的协议米-terphenyls 5和磺酰米-terphenyls 6选自取代的查耳酮开发1和烯丙基砜2经由[3C + 3C]环以良好的收率。NaH介导的环化反应具有无过渡金属的条件。查耳酮1与官能团耐受性很容易通过取代的苯甲醛的克莱森-施密特缩合制备3与苯乙酮4以定性收率下含水碱性甲醇溶液。

  DOI：

  10.1016/j.tet.2013.09.036

文献信息

• One-pot synthesis of multifunctionalized m-terphenyls
  作者：Meng-Yang Chang、Chieh-Kai Chan、Shin-Ying Lin、Ming-Hao Wu

  DOI：10.1016/j.tet.2013.09.036

  日期：2013.11

  one-step synthetic protocol toward multifunctionalized m-terphenyls 5 and sulfonyl m-terphenyls 6 is developed from substituted chalcones 1 and allyl sulfone 2 in good yields via a [3C+3C] annulation. The NaH-mediated annulation features transition metal catalyst-free condition. Chalcones 1 with the functional groups tolerance are easily prepared via Claisen–Schmidt condensation of substituted benzaldehydes

  朝向多官能化一种简便一步法合成的协议米-terphenyls 5和磺酰米-terphenyls 6选自取代的查耳酮开发1和烯丙基砜2经由[3C + 3C]环以良好的收率。NaH介导的环化反应具有无过渡金属的条件。查耳酮1与官能团耐受性很容易通过取代的苯甲醛的克莱森-施密特缩合制备3与苯乙酮4以定性收率下含水碱性甲醇溶液。
• One‐Pot Construction of Sulfonyl Benzonorcaradienes
  作者：Meng‐Yang Chang、Chun‐Yi Lin

  DOI：10.1002/adsc.202300012

  日期：2023.3.21

  We report here on a one-pot stereoselective synthesis of strained sulfonyl benzonorcaradienes, which proceeds through base-mediated tandem annulation of o-bis-sulfonylmethyl arenes with diversified chalcones (α,β-unsaturated carbonyls) via intermolecular desulfonylative cyclopropanation, followed by intramolecular condensation. A plausible mechanism is proposed and discussed. The proposed synthetic

  我们在这里报告了应变磺酰基苯并碳二烯的一锅法立体选择性合成，它通过碱介导的o -双磺酰甲基芳烃与多种查耳酮（α,β-不饱和羰基）的串联环化通过分子间脱磺酰化环丙烷化反应进行，然后进行分子内缩合. 提出并讨论了一种合理的机制。拟议的合成路线形成两个碳-碳单 (CC) 键和一个碳-碳双 (C=C) 键。
• Effect of ring A and ring B substitution on the cytotoxic potential of pyrazole tethered chalcones
  作者：Kunal Nepali、Kanika Kadian、Ritu Ojha、Rajni Dhiman、Atul Garg、Gagandip Singh、Abhishek Buddhiraja、Preet Mohinder Singh Bedi、Kanaya Lal Dhar

  DOI：10.1007/s00044-011-9824-9

  日期：2012.10

  Chalcone is an aromatic ketone that forms the central core for a variety of important biological compounds, which are collectively known as chalcones. The cytotoxic potential of chalcones which consists of C-6-C-3-C-6 units gets enhanced by the incorporation of pyrazole ring as proved by our earlier studies. Thus in the present work, pyrazoles of chalcones with ring A substituted by furan, naphthalene and variety of substituted phenyl rings has been prepared and evaluated for in vitro cytotoxic activity against PC-3, OVCAR, IMR-32, HEP-2 human cancer cell lines.All the synthesized compounds were evaluated for in vitro cytotoxicity against PC-3, OVCAR, IMR-32, HEP-2 human cancer cell lines. Compound 68 was found to be the most potent showing broad spectrum of cytotoxicity against all the cell lines .
• One-pot synthesis of multifunctionalized cyclopropanes
  作者：Meng-Yang Chang、Yi-Chia Chen、Chieh-Kai Chan

  DOI：10.1016/j.tet.2014.02.024

  日期：2014.4

  A facile one-step synthetic protocol toward multifunctionalized cyclopropanes 4 is developed from substituted chalcones 1 and sulfones 2 in good yields via a [2C+1C] annulation. (c) 2014 Elsevier Ltd. All rights reserved.
• One-pot synthesis of multisubstituted quaterphenyls and cyclopropanes
  作者：Meng-Yang Chang、Chieh-Kai Chan、Shin-Ying Lin、Ming-Hao Wu

  DOI：10.1016/j.tet.2013.09.060

  日期：2013.11

  quaterphenyls 3 or cyclopropanes 4 is developed from substituted chalcones 1 and sulfones 2 in good yields via a regioselective [3C+3C] or [1C+2C] annulation. The reaction features mild conditions, multisubstitution, and functional groups tolerance and is transition metal catalyst-free. The protocol provides a novel alternative to the conventional methodologies for the synthesis of quaterphenyls or

  朝向多官能化quaterphenyls一种有效的一步合成路线3或环丙烷4选自取代的查耳酮开发1和砜2以良好的收率通过区域选择性[3C + 3C]或[1C + 2C]环。该反应具有温和的条件，多取代和对官能团的耐受性，并且不含过渡金属催化剂。该方案为合成四苯基或环丙烷的常规方法提供了一种新颖的替代方法。