2,4-chloro-2-((E)-2-nitrovinyl)phenol | 1310493-82-3

• 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: 2,4-chloro-2-((E)-2-nitrovinyl)phenol
• 英文别名: (E)-2,4-dichloro-6-(2-nitrovinyl)phenol；2,4-dichloro-6-[(E)-2-nitroethenyl]phenol
• CAS: 1310493-82-3
• 化学式: C₈H₅Cl₂NO₃
• 分子量: 234.039
• InChiKey: UEJUCWDGSKXTKG-OWOJBTEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  2,4-chloro-2-((E)-2-nitrovinyl)phenol 在 sodium tetrahydroborate 、 乙醇 、 碘苯二乙酸 、 4-((R)-(naphthalen-1-ylmethoxy)((1S,2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl)quinolin-6-ol 、 四丁基碘化铵 、 三乙胺 作用下， 以 1,4-二氧六环 、 氯仿 、 乙腈 为溶剂， 反应 1.5h， 生成 methyl (1R,3aR,8bR)-5,7-dichloro-3a-nitro-1-phenyl-3a,8b-dihydro-1H-benzofuro[2,3-c]pyrrole-1-carboxylate
  参考文献：
  名称：

  2-硝基苯并呋喃和异氰乙酸酯的无金属非对映和对映选择性脱芳香缩甲醛[3 + 2]环加成

  摘要：

  2-硝基苯并呋喃和α-芳基-α-异氰基乙酸酯的非对映和对映选择性脱芳香形式[3 + 2]环加成得到带有3 a ,8 b -二氢-1 H -苯并呋喃[2,3- c ]的三环化合物具有三个连续立体中心的吡咯框架。该反应是通过铜醚有机催化剂实现的。获得的反应产物具有几乎完全的非对映选择性，并且对于许多取代的2-硝基苯并呋喃和异氰乙酸酯具有优异的对映体过量。

  DOI：

  10.1021/acs.orglett.2c00427
• 作为产物：
  描述：

  硝基甲烷 、 3,5-二氯水杨醛 在 ammonium acetate 、 溶剂黄146 作用下， 反应 0.25h， 以39%的产率得到2,4-chloro-2-((E)-2-nitrovinyl)phenol
  参考文献：
  名称：

  2-硝基苯并呋喃和异氰乙酸酯的无金属非对映和对映选择性脱芳香缩甲醛[3 + 2]环加成

  摘要：

  2-硝基苯并呋喃和α-芳基-α-异氰基乙酸酯的非对映和对映选择性脱芳香形式[3 + 2]环加成得到带有3 a ,8 b -二氢-1 H -苯并呋喃[2,3- c ]的三环化合物具有三个连续立体中心的吡咯框架。该反应是通过铜醚有机催化剂实现的。获得的反应产物具有几乎完全的非对映选择性，并且对于许多取代的2-硝基苯并呋喃和异氰乙酸酯具有优异的对映体过量。

  DOI：

  10.1021/acs.orglett.2c00427

文献信息

• Stereocontrolled construction of 3H-furo[3,4-b]chromen-1(9H)-one scaffolds via organocatalyzed Michael addition and the following intramolecular dehydration
  作者：L.-Y. Cui、Y.-H. Wang、S.-R. Chen、Y.-M. Wang、Z.-H. Zhou

  DOI：10.1039/c5ra17503h

  日期：——

  An efficient approach for the stereocontrolled construction of 3H-furo[3,4-b]chromen-1(9H)-one skeleton has been successfully developed through a sequential Michael addition/intramolecular dehydration strategy. The Michael addition of tetronic acid to 2-((E)-2-nitrovinyl)phenols catalyzed by a bifunctional squaramide derived from L-tert-leucine, and the subsequent intramolecular dehydration promoted

  通过顺序迈克尔加成/分子内脱水策略，成功开发了一种立体控制3 H-呋喃并[3,4- b ] chromen-1（9 H）-骨架的有效方法。迈克尔加成特窗酸的2 - （（Ë）-2-硝基乙烯基）苯酚通过衍生自双官能squaramide催化大号-叔-亮氨酸，和由浓硫酸促进了随后的分子内脱水，顺利进行，得到相应的药学上有价值的3 H-呋喃并[3,4- b ] chromen-1（9 H）-one，可接受的收率为ee的79–97％。
• Neighboring<i>ortho</i>-Hydroxy Group Directed Catalytic Asymmetric Triple Domino Reactions of Acetaldehyde with (<i>E</i>)-2-(2-Nitrovinyl)phenols
  作者：Dhevalapally B. Ramachary、P. Srinivasa Reddy、M. Shiva Prasad

  DOI：10.1002/ejoc.201402182

  日期：2014.5

  neighboring ortho-hydroxy group participation in the pretransition state of enamine- and iminium-based triple domino reactions for high reactions rates and asymmetric induction. Enantiomerically pure, drug-like chromanes and tetrahydro-6H-benzo[c]chromenes having three to four contiguous stereocenters are synthesized through triple domino Michael/aldol/oxa-Michael reactions catalyzed by (R)-2-diphenyl[(trim

  在此，我们展示了利用相邻的邻羟基参与基于烯胺和亚胺的三重多米诺反应的预转变状态，以实现高反应速率和不对称诱导。通过 (R)-2-二苯基 [(三甲基甲硅烷基) 催化的三重多米诺迈克尔/醛醇/氧杂-迈克尔反应合成对映体纯的药物样色满和四氢-6H-苯并[c]色烯具有三到四个连续的立体中心氧]甲基}吡咯烷，然后在温和条件下由简单前体进行 Wittig 和 Michael/Wittig-Horner 反应。
• Stereocontrolled Construction of 3,4‐Dihydrocoumarin Scaffolds with a Quaternary Amino Acid Moiety <i>via</i> Chiral Squaramide‐Catalyzed Cascade Michael Addition/Lactonization Reaction
  作者：Yuehua Wang、Jianping Pan、Rongrong Jiang、Youming Wang、Zhenghong Zhou

  DOI：10.1002/adsc.201500862

  日期：2016.1.21

  An asymmetric tandem Michael addition–lactonization between ortho‐nitrovinylphenols and azalactones was investigated for constructing 3,4‐dihydrocoumarin backbones with a quaternary amino acid moiety. Under the catalysis of the chiral squaramide derived from L‐tert‐leucine, a wide range of substituted (E)‐2‐(2‐nitrovinyl)phenols and azalactones were well tolerated in this tandem reaction to provide

  研究了邻硝基硝基乙烯基苯酚和氮杂内酯之间的不对称串联迈克尔加成-内酯化反应，以构建具有季氨基酸部分的3,4-二氢香豆素骨架。下从得到的手性squaramide的催化大号-叔-亮氨酸，一个宽范围的取代的（的ë）-2-（2-硝基乙烯基）苯酚和azalactones物以及在该串联反应耐受以提供相应的生物显著3,4二氢香豆素衍生物，收率高，非对映和对映选择性高。
• Design, synthesis, molecular docking, and biological evaluation of N-methyl-3-nitro-4-(nitromethyl)-4H-chromen-2-amine derivatives as potential anti-cancer agents
  作者：A. Parthiban、J. Muthukumaran、A. Moushumi Priya、S. Jayachandran、R. Krishna、H. Surya Prakash Rao

  DOI：10.1007/s00044-013-0642-0

  日期：2014.2

  A series of N-methyl-3-nitro-4-(nitromethyl)4H-chromen-2-amine derivatives 8 were synthesized from 2-((E)-2-nitrovinyl)phenol 7 and ((E)-N-methyl)-1-(methylthio)-2-nitroethenamine 5. The cytotoxic activity of these molecules was tested against two cancer cell lines namely HeLa (cervical cancer) and HEp-2 (epidermoid laryngeal carcinoma). Among them, two molecules (4H-chromenes 8h and 8i) displayed potent anti-proliferative activity with IC50 values of 115.04 and 18.96 mu M for HeLa and 86.94 and 25.08 mu M for Hep-2 cell lines, respectively. Morphological evaluation of the cell lines revealed that both 8h and 8i induce the apoptotic process. Molecular docking studies of all the 4H-chromenes 8 with antiapoptotic Bcl-2, Bcl-w, and Bcl-xL proteins revealed that the 4H-chromenes 8h and 8i have good docking score and thus corroborated in vitro studies. Furthermore, evaluation of Lipinski and ADMET properties revealed their drug-like pharmacokinetic profiles. Thus, 4H-chromenes 8h and 8i exhibit promising anti-cancer properties and can be used as lead compounds for further development.
• Enantioselective organocatalytic synthesis of medicinally privileged 2-amino-4H-chromene-3-carbonitriles via a cascade process
  作者：Zhiyun Du、Woon-Yew Siau、Jian Wang

  DOI：10.1016/j.tetlet.2011.09.030

  日期：2011.11

  An efficient organocatalytic cascade approach toward medicinally privileged 2-amino-4H-chromene-3-carbonitriles is reported. The enantioselective synthesis of these compounds is achieved in high yields and good to high ee values (up to 96% yield and 89% ee) using bifunctional amine-thiourea organocatalysts developed in our laboratory. (C) 2011 Elsevier Ltd. All rights reserved.