(E)-1-phenyl-3-(2-(tosylamino)phenyl)prop-2-en-1-one | 1195694-52-0

• 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: (E)-1-phenyl-3-(2-(tosylamino)phenyl)prop-2-en-1-one
• 英文别名: (E)-4-methyl-N-(2-(3-oxo-3-phenylprop-1-en-1-yl)phenyl)benzenesulfonamide；4-Methyl-N-{2-[(E)-3-oxo-3-phenylprop-1-en-1-yl]phenyl}benzenesulfonamide；4-methyl-N-[2-[(E)-3-oxo-3-phenylprop-1-enyl]phenyl]benzenesulfonamide
• CAS: 1195694-52-0
• 化学式: C₂₂H₁₉NO₃S
• 分子量: 377.464
• InChiKey: VWQJOJJITJJDDF-DTQAZKPQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  71.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-1-phenyl-3-(2-(tosylamino)phenyl)prop-2-en-1-one 在 三氟甲磺酸 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 12.0h， 以90%的产率得到2-苯基喹啉
  参考文献：
  名称：

  通过酸催化2-（甲苯磺酰基氨基）查耳酮的环脱水合成喹啉

  摘要：

  研究了（E）-3-[（2-甲苯磺酰基氨基）苯基] -1-（杂）芳基丙-2-烯-1-酮的酸催化环脱水为2-取代的喹诺酮。反应通过（E，Z）-异构化的关键步骤进行，随后进行分子内环化，以高收率得到目标化合物。

  DOI：

  10.1007/s10593-017-2010-3
• 作为产物：
  描述：

  (E)-3-(2-nitrophenyl)-1-phenylprop-2-en-1-one 在 吡啶 、 铁粉 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 生成 (E)-1-phenyl-3-(2-(tosylamino)phenyl)prop-2-en-1-one
  参考文献：
  名称：

  有机催化对映选择性级联Aza-Michael / Michael加成反应，用于合成高度官能化的四氢喹啉和四氢色氮喹啉

  摘要：

  AbstractAn efficient organocatalytic highly asymmetric cascade aza‐Michael/Michael addition reaction for the synthesis of tetrahydroquinolines and tetrahydrochromanoquinolines has been developed. This cascade reaction proceeds well at low catalyst loading with a broad substrate scope, furnishing the desired products in excellent yields with excellent diastereoselectivities and enantioselectivities (up to >99:1 dr, 99% ee) under mild conditions. Importantly, it is the first catalytic asymmetric method for tetrahydrochromanoquinolines. This protocol provides a straightforward entry to highly functionalized chiral tetrahydroquinoline and tetrahydrochromanoquinoline derivatives from simple starting materials.magnified image

  DOI：

  10.1002/adsc.201300670

文献信息

• Asymmetric domino aza-Michael–Michael reaction of o-N-protected aminophenyl α,β-unsaturated ketones: construction of chiral functionalized tetrahydroquinolines
  作者：Shinae Kim、Ki-Tae Kang、Sung-Gon Kim

  DOI：10.1016/j.tet.2014.05.114

  日期：2014.8

  The diastereo- and enantioselective synthesis of 2,3,4-trisubstituted tetrahydroquinolines has been developed through organocatalytic domino aza-Michael–Michael reaction of o-N-tosylaminophenyl α,β-unsaturated ketones with nitroalkenes. This useful and simple domino process afforded diverse highly functionalized tetrahydroquinolines, some of which are not easily accessible using other methodologies

  的2,3,4-三取代的四氢喹啉的diastereo-和对映选择性合成已经通过的有机催化多米诺氮杂迈克尔-反应开发ø - Ñ -tosylaminophenylα，β不饱和酮与硝基烯烃。这种有用且简单的多米诺工艺提供了多种高度官能化的四氢喹啉，其中一些不易使用其他方法获得，收率高且非对映和对映选择性极佳（高达> 30：1 dr，> 99％ee）。
• 신규한 알데히드기를 포함하는 키랄 1,4-디히드로퀴놀린유도체와 이의 제조방법
  申请人：Kyonggi University Industry & Academia Cooperation Foundation 경기대학교 산학협력단(220050169907) BRN ▼135-82-10872

  公开号：KR101716586B1

  公开（公告）日：2017-03-14

  본 발명은 광학활성을 갖는 알데히드기를 포함하는 1,4-디히드로퀴놀린을 얻을 수 있는 제조방법에 관한 것으로, 2-아미노페닐 알파,베타-불포화 케톤 유도체와 알키닐알데히드 화합물의 촉매적 첨가-고리화(asymmetric addition-cyclization) 반응을 프로린으로부터 유래한 키랄 아민 유기촉매를 이용하여 수행한 것이다. 상기 방법은 알데히드기를 포함하는 1,4-디히드로퀴놀린을 높은 화학적 수득률과 거울상 이성질체를 선택적으로 제조할 수 있다.

  这项发明涉及一种制备含有光学活性醛基的1,4-二氢喹啉的方法，通过使用源自脯氨酸的手性胺有机催化剂，在2-氨基苯基α,β-不饱和酮衍生物和烷基醛化合物的催化加成-环化反应中进行。该方法可以高效地选择性制备含有醛基的1,4-二氢喹啉，具有高化学产率和手性镜像异构体。
• Asymmetric One-Pot Synthesis of 1,4-Dihydroquinolines via an Organocatalytic Aza-Michael/Michael Cascade Strategy
  作者：Yona Lee、Seungpyeong Heo、Sung-Gon Kim

  DOI：10.1002/adsc.201401176

  日期：2015.5.4

  A synthetic method for the construction of fully substituted enantioenriched 1,4‐dihydroquinolines using an organocatalytic aza‐Michael/Michael cascade reaction has been developed. The asymmetric reaction of 2‐(tosylamino)phenyl α,β‐unsaturated ketones with alkynyl aldehydes, promoted by diphenylprolinol O‐TMS ether as an organocatalyst, generated chiral 1,4‐dihydroquinolines in good to high yields

  开发了一种使用有机催化氮杂-迈克尔/迈克尔级联反应构建完全取代的对映体富集的1,4-二氢喹啉的合成方法。由二苯基脯氨醇O -TMS醚作为有机催化剂促进的2-（甲苯磺酰基氨基）苯基α，β-不饱和酮与炔醛的不对称反应生成手性的1,4-二氢喹啉，具有良好的高收率和优异的对映选择性（高达97 ％ee）。
• Preparation of functional benzofurans and indoles via chemoselective intramolecular Wittig reactions
  作者：Yu-Ting Lee、Yeong-Jiunn Jang、Siang-en Syu、Shu-Chi Chou、Chia-Jui Lee、Wenwei Lin

  DOI：10.1039/c2cc33972b

  日期：——

  A general preparation of new types of benzofurans, benzothiophenes and indoles is realized via chemoselective intramolecular Wittig reactions with the corresponding ester, thioester and amide functionalities using in situ formed phosphorus ylides as key intermediates. The reaction conditions are very mild, and numerous Michael acceptors and commercially available acid chlorides can be applied very

  新型苯并呋喃，苯并噻吩和吲哚的一般制备方法是通过化学选择性分子内Wittig反应，使用原位形成的磷化磷作为主要中间体，与相应的酯，硫酯和酰胺官能团进行的。反应条件非常温和，可以一步一步高效地应用许多迈克尔受体和市售的酰氯。
• Asymmetric synthesis of CF₃-containing tetrahydroquinoline via a thiourea-catalyzed cascade reaction
  作者：Yuanyuan Zhu、Boyu Li、Cui Wang、Zhenghao Dong、Xiaoling Zhong、Kairong Wang、Wenjin Yan、Rui Wang

  DOI：10.1039/c7ob01013c

  日期：——

  An organocatalytic asymmetric method for the synthesis of 2-CF3 tetrahydroquinoline has been achieved. The cascade reaction of 2-aminochalcones with β-CF3 nitroalkenes afforded the products bearing three contiguous stereogenic centers in good yields with excellent diastereoselectivities and enantioselectivities.

  已经实现了用于合成2-CF 3四氢喹啉的有机催化不对称方法。2- aminochalcones与β-CF级联反应3个硝基烯烃得到轴承产品以良好的收率具有优良的非对映选择性和对映选择性三个连续的手性中心。