(E)-3-(4-chlorophenyl)-2-nitroprop-2-en-1-ol | 1169855-54-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: (E)-3-(4-chlorophenyl)-2-nitroprop-2-en-1-ol
• CAS: 1169855-54-2
• 化学式: C₉H₈ClNO₃
• 分子量: 213.62
• InChiKey: MHXUZEOICLIWHY-WEVVVXLNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-3-(4-chlorophenyl)-2-nitroprop-2-en-1-ol 在 三乙胺 作用下， 以 二氯甲烷 、 甲苯 、 苯 为溶剂， 反应 1.33h， 生成 (3aS,4S,8R,9R,9aS)-8-benzoyl-9-(4-chlorophenyl)-4-phenyltetrahydrofuro[3,4-c]isoxazolo[2,3-b]isoxazolo-3(1H)-one
  参考文献：
  名称：

  通过串联[4 +1] / [3 + 2]环化加成的硫叶立德和硝基烯烃对映异构地构建氧杂和氮杂角的三喹烷。

  摘要：

  已经开发了硫代烷基化物和链烯连接的硝基烯烃的正式[4 +1] / [3 + 2]环加成序列。（R）-苯酚衍生的手性硫化物的使用导致不对称过程，该过程允许以良好至优异的非对映选择性和对映选择性制备氧杂-和氮杂-角的三喹烷。

  DOI：

  10.1021/ol303363r
• 作为产物：
  描述：

  4-氯苯甲醛 在 咪唑 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 生成 (E)-3-(4-chlorophenyl)-2-nitroprop-2-en-1-ol
  参考文献：
  名称：

  Asymmetric synthesis of tetrahydropyran[3,2-c]quinolinones via an organocatalyzed formal [3 + 3] annulation of quinolinones and MBH 2-naphthoates of nitroolefin

  摘要：

  An efficient asymmetric and enantio-swithchable organocatalytic [3 + 3] annulation reaction using MBH-2-naphthoates of nitroalkenes and 4-hydroxyquinolin-2(1H)-ones has been developed. Densely substituted tetrahydropyrano[3,2-c]quinolinones scaffolds with two adjacent stereogenic centers are obtained with high yield (up to 95% yield) and good stereoselectivities (up to >20:1 dr and 96% ee) in an enantio-switchable manner. Furthermore, gram scale synthesis was achieved and the nitro group could easily transform into an amino group without any appreciable loss in the diastereo- and enantioselectivity. (C) 2019 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.cclet.2019.08.040

文献信息

• 1,3-Dipolar Cycloaddition on Baylis-Hillman Adducts: Novel Synthesis of Pyrrolidines, Spiropyrrolidines, and Spiropyrrolizidines
  作者：Manickam Bakthadoss、Nagappan Sivakumar、Anthonisamy Devaraj、Duddu Sharada

  DOI：10.1055/s-0030-1260053

  日期：2011.7

  A facile regio- and stereoselective synthesis of functionalized pyrrolidines, spiropyrrolidines, and spiropyrrolizidines using the Baylis-Hillman adducts derived from nitroolefins via intermolecular [3+2]-cycloaddition reaction is reported. Baylis-Hillman reaction - intermolecular [3+2] cycloaddition - azomethine ylides - 1,3-dipolar cycloaddition - pyrrolidines - spiro compounds

  报道了使用衍生自硝基烯烃的Baylis-Hillman加合物通过分子间[3 + 2]-环加成反应的功能性吡咯烷，螺吡咯烷和螺吡咯并核苷的容易的区域和立体选择性合成。 Baylis-Hillman反应-分子间[3 + 2]环加成-偶氮甲亚胺-1,3-偶极环加成-吡咯烷-螺环化合物
• Cooperative Dienamine/Hydrogen-Bonding Catalysis: Enantioselective Formal [2+2] Cycloaddition of Enals with Nitroalkenes
  作者：Garazi Talavera、Efraím Reyes、Jose L. Vicario、Luisa Carrillo

  DOI：10.1002/anie.201200269

  日期：2012.4.23

  Two can play this game: The title reaction is catalyzed by a chiral secondary amine in the presence of an achiral thiourea for the enantio‐ and diastereoselective synthesis of highly functionalized cyclobutanes (see scheme; TMS=trimethylsilyl). Mechanistically, two consecutive Michael reactions proceed through an unprecedented combination of an dienamine/iminium activation mode.

  两个可以玩这个游戏：在手性仲胺的存在下，手性仲胺催化标题反应，用于高功能化环丁烷的对映和非对映选择性合成（参见方案； TMS =三甲基甲硅烷基）。从机理上讲，两个连续的迈克尔反应是通过前所未有的二烯胺/亚胺活化方式进行的。
• A remarkable solvent effect on the reaction of 4-hydroxycoumarin with (E)-3-aryl-2-nitroprop-2-enol: Facile synthesis of highly substituted furo/pyrano[3,2-c]chromenes
  作者：Shivendra Singh、Anvita Srivastava、Shaikh M. Mobin、Sampak Samanta

  DOI：10.1039/c4ra10610e

  日期：——

  A remarkable solvent effect on the reaction of 4-hydroxycoumarin derivatives with (E)-3-aryl/hetero-aryl-2-nitroprop-2-enols has been observed in water and DMSO media. This result was employed for the straightforward syntheses of new functionalized furo/pyrano[3,2-c]chromenes in 63–93% yields and diasteromeric ratio up to ≤99 : 1. Moreover, a simple, mild, efficient and catalyst-free one-pot method

  在水和DMSO介质中，已观察到对4-羟基香豆素衍生物与（E）-3-芳基/杂芳基-2-硝基丙-2-烯醇的反应具有显着的溶剂作用。该结果用于新型官能化的呋喃/吡喃并[3,2- c ]色烯的直接合成，产率为63-93％，非对映异构体比例最高为≤99：1。此外，该方法简单，温和，高效且无催化剂一锅法可能会为香豆素核上的呋喃/吡喃环的成环提供另一种合成策略。此外，水对该反应的速率和选择性（产物）显示出显着的积极作用。
• Access to Substituted Carbazoles in Water by a One-Pot Sequential Reaction of α,β-Substituted Nitro Olefins with 2-(3-Formyl-1<i>H</i>-indol-2-yl)acetates
  作者：Soumen Biswas、Anuradha Dagar、Anvita Srivastava、Sampak Samanta

  DOI：10.1002/ejoc.201500470

  日期：2015.7

  interesting new multifunctional carbazole scaffolds have been prepared in good to excellent yields by an organocatalytic one-pot two-step sequential reaction between α-alkyl-β-substituted nitro olefins or α-alkyl-δ-substituted nitro-dienes and 2-(3-formyl-1H-indol-2-yl)acetates in water at room temperature followed by treatment with 2 n HCl under mild conditions. This one-pot, organocatalytic, oxidant-free

  通过α-烷基-β-取代硝基烯烃或α-烷基-δ-取代硝基二烯与2 -(3-formyl-1H-indol-2-yl)acetates 在室温下的水中，然后在温和条件下用 2n HCl 处理。这种一锅法、有机催化、无氧化剂、温和且环保的工艺可以提供一种强大的替代合成方案，以快速获得与生物活性天然咔唑结构相似的 3-烷基取代咔唑骨架。此外，使用这种合成方法已经有效地制备了具有生物学意义的环状酰亚胺和喹啉酮稠合咔唑。
• Stereoselective Synthesis of 3‐Oxabicyclo[3.3.1]Nonan‐2‐Ones via a Domino Reaction Catalyzed by Modularly Designed Organocatalysts
  作者：Ramarao Parella、Satish Jakkampudi、Hadi Arman、John C.‐G. Zhao

  DOI：10.1002/adsc.201800987

  日期：2019.1.11

  1]nonan-2-one derivatives with four contiguous stereogenic centers, including one tetrasubstituted stereogenic center, was realized through an organocatalytic domino Michael-hemiacetalization-Michael reaction of (E)-3-aryl-2-nitroprop-2-enols and (E)-7-aryl-7-oxohept-5-enals followed by a PCC oxidation. Using the modularly designed organocatalysts (MDOs) self-assembled from cinchona alkaloid derivatives and

  通过(E )-3-芳基-2-硝基丙-2-烯醇和(E)-7-芳基-7-氧代庚基-5-烯醇，然后进行 PCC 氧化。使用由金鸡纳生物碱衍生物和氨基酸在反应介质中自组装的模块化设计的有机催化剂（MDO），以良好的产率（高达84%）、优异的非对映选择性（> 99:1 dr）和高的产率获得了标题产物。对映选择性（高达 96% ee）。