3-氯-3-苯基-2-苯并呋喃-1-酮 | 18852-53-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 中文名称: 3-氯-3-苯基-2-苯并呋喃-1-酮
• 英文名称: 3-chloro-3-phenylphthalide
• 英文别名: 3-Chloro-3-phenylisobenzofuranone；3-chloro-3-phenyl-2-benzofuran-1(3H)-one；3-chloro-3-phenyl-2-benzofuran-1-one；3-chloro-3-phenyl-3H-isobenzofuran-1-one；3-Chlor-3-phenyl-phthalid；3-chloro-3-phenyl-1-(3H)-isobenzofuranone；3-Chloro-3-phenylisobenzofuran-1(3H)-one
• CAS: 18852-53-4
• 化学式: C₁₄H₉ClO₂
• 分子量: 244.677
• InChiKey: CAYYZOKWYGGFAV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-氯-3-苯基-2-苯并呋喃-1-酮 在 氯化亚砜 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 为溶剂， 反应 52.0h， 生成 6-benzyloxycarbonylamino-2-((3-oxo-1-phenyl)-1-propoxy-1,3-dihydroisoindol-2-yl)hexanoic acid methyl ester
  参考文献：
  名称：

  Small-Molecule Inhibitors of the MDM2-p53 Protein−Protein Interaction Based on an Isoindolinone Scaffold

  摘要：

  From a set of weakly potent lead compounds, using in silico screening and small library synthesis, a series of 2-alkyl-3-aryl-3-alkoxyisoindolinones has been identified as inhibitors of the MDM2-p53 interaction. Two of the most potent compounds, 2-benzyl-3-(4-chlorophenyl)-3-(3-hydroxypropoxy)-2,3-dihydroisoindol-1-one (76; IC50 = 15.9 +/- 0.8 mu M) and 3-(4-chlorophenyl)-3-(4-hydroxy-3,5-dimethoxybenzyloxy)-2-propyl-2,3-dihydroisoindol-1-one (79; IC50) 5.3 (0.9 mu M), induced p53-dependent gene transcription, in a dose-dependent manner, in the MDM2 amplified, SJSA human sarcoma cell line.

  DOI：

  10.1021/jm0601194
• 作为产物：
  描述：

  邻苯甲酰苯甲酸 在 氯化亚砜 作用下， 反应 5.0h， 生成 3-氯-3-苯基-2-苯并呋喃-1-酮
  参考文献：
  名称：

  抗惊厥药 3-氨基甲酰基-异喹啉酮：3-氨基甲酰基-4-芳基-异喹啉-1 (2H) -ones 的合成和抗惊厥活性

  摘要：

  描述了十九个 3-cabamoyl-4-aryl-isoquinolin-1 (2H) -ones 的合成。该化合物在最大电击试验（腹膜内给药）中具有抗惊厥作用。代表性物质是3-氨基甲酰基-2-异丙基-4-(4-氯苯基)-异喹啉-1(2H)-one，ED50=2.1·10-4mol/kg。效力是苯妥英 (ED50 = 0.44 · 10−4 mol / kg) 的 20%。

  DOI：

  10.1002/ardp.2503241007

文献信息

• Preparation of 13-Substituted 8<i>H</i>-Dibenzo[<i>a</i>,<i>g</i>]quinolizin-8-ones by Intramolecular Wittig-Horner Reaction of Dialkyl 2-(<i>o</i>-Acylbenzoyl)-1,2-dihydro-1-isoquinolylphosphonates
  作者：Kin-ya Akiba、Yoshio Negishi、Naoki Inamoto

  DOI：10.1246/bcsj.57.2188

  日期：1984.8

  Dialkyl 2-(o-acylbenzoyl)-1,2-dihydro-1-isoquinolyl-phosphonates (1) were prepared by reactions of isoquinoline, o-acylbenzoyl chloride, and trialkyl phosphites. Treatment of 1 with lithium diisopr...

  二烷基 2-(o-酰基苯甲酰基)-1,2-二氢-1-异喹啉基膦酸酯 (1) 通过异喹啉、邻酰基苯甲酰氯和亚磷酸三烷基酯的反应制备。用锂离子分散剂处理1...
• A Facile Synthesis of Novel Cyclic Esters of γ-Keto Acid Derivatives by Heck Coupling Reaction
  作者：Nellisara D. Shashikumar、G. Krishnamurthy、Halehatti S. Bhojyanaik

  DOI：10.1002/jhet.1898

  日期：2014.8

  γ-Keto acids and esters are highly useful compounds in organic synthesis, because a number of five-membered carbocycles and various other heterocycles can be readily obtained from them. A number of γ-keto acids derivatives have been synthesized with high yield by Heck coupling reaction with different alkenes using Pd(OAc)2 as catalyst in dioxane solvent. The obtained products were characterized by

  γ-酮酸和酯是有机合成中非常有用的化合物，因为可以很容易地从中获得许多五元碳环和各种其他杂环。以Pd（OAc）2为催化剂，通过与不同烯烃的Heck偶联反应，高产率合成了许多γ-酮酸衍生物。二恶烷溶剂。所得产物通过元素分析，IR，质子NMR和质谱研究来表征。
• Synthesis and Properties of Peroxy Esters Having a Benzophenone Chromophore
  作者：Hiromi Kumura、Tomoyuki Nakamura、Yoshiki Higuchi、Shuji Suyama

  DOI：10.1246/bcsj.64.3538

  日期：1991.12

  Diperoxy esters having a benzophenone chromophore have been successfully synthesized from the reaction of 3-chloro-3-phenylphthalide (1) with 2,5-dihydroperoxy-2,5-dimethyl-3-hexyne (4a) or 2,5-dihydroperoxy-2,5-dimethylhexane (4b). The corresponding diperoxy esters had a UV absorption above 300 nm. The free radicals produced during the photolysis of these compounds initiated the radical polymerization

  通过 3-氯-3-苯基苯酞 (1) 与 2,5-二氢过氧-2,5-二甲基-3-己炔 (4a) 或 2,5-二氢过氧- 2,5-二甲基己烷 (4b)。相应的双过氧酯在 300 nm 以上具有紫外吸收。这些化合物在光解过程中产生的自由基在室温下在紫外光下引发了甲基丙烯酸甲酯的自由基聚合。
• [EN] ISOINDOLIN-1-ONE DERIVATIVES<br/>[FR] DÉRIVÉS D'ISOINDOLIN-1-ONE
  申请人：CANCER REC TECH LTD

  公开号：WO2006024837A1

  公开（公告）日：2006-03-09

  A compound of formula (1) or a prodrug and/or pharmaceutically acceptable salt thereof, wherein X is selected from O, N or S; R1 is selected from hydrogen, halo, hydroxy, substituted or unsubstituted alkyl, substituted or unsubstituted hydroxyalkyl, substituted or unsubstituted alkylamine, alkoxy, substituted or unsubstituted aryl or heteroaryl, and substituted or unsubstituted aralkyl or heteroaralkyl; R2 is selected from hydrogen, halo, hydroxy, substituted or unsubstituted alkyl, substituted or unsubstituted hydroxyalkyl substituted or unsubstituted alkylamine, alkoxy, substituted or unsubstituted aryl or heteroaryl, and substituted or unsubstituted aralkyl or heteroalkyl; R3 is selected from hydrogen, halo, hydroxy, substituted or unsubstituted alloy substituted or unsubstituted hydroxyalkyl, substituted or unsubstituted alkylamine alkoxy, substituted or unsubstituted aryl or heteroaryl, and substituted or unsubstituted aralkyl or heteroalkyl; and R4-R7, is used to represent groups R4, R5, R6 and R7 which are independently selected from H, OH, alkyl, alkoxy, alkylamine, hydroxyalkyl, halo, CF3, NH2, NO2, COOH, C=0.

  式（1）的化合物或其前药和/或药用可接受的盐，其中X选择自O、N或S；R1选择自氢、卤素、羟基、取代或未取代的烷基、取代或未取代的羟基烷基、取代或未取代的烷基胺、烷氧基、取代或未取代的芳基或杂环芳基、取代或未取代的芳基或杂环芳基；R2选择自氢、卤素、羟基、取代或未取代的烷基、取代或未取代的羟基烷基、取代或未取代的烷基胺、烷氧基、取代或未取代的芳基或杂环芳基、取代或未取代的芳基或杂环芳基；R3选择自氢、卤素、羟基、取代或未取代的合金取代或未取代的羟基烷基、取代或未取代的烷基胺烷氧基、取代或未取代的芳基或杂环芳基、取代或未取代的芳基或杂环芳基；R4-R7，用于表示独立选择自H、OH、烷基、烷氧基、烷基胺、羟基烷基、卤素、CF3、NH2、NO2、COOH、C=0的基团R4、R5、R6和R7。
• Relay Catalysis Using a Rhodium Complex/Chiral Brønsted Acid Binary System: Enantioselective Reduction of a Carbonyl Ylide as the Reactive Intermediate
  作者：Masahiro Terada、Yasunori Toda

  DOI：10.1002/anie.201107805

  日期：2012.2.27

  Pass the baton: A one‐pot relay catalysis for a carbonyl ylide formation/enantioselective reduction sequence using a dirhodium(II) tetracarboxylate and chiral phosphoric acid catalyst system is described. The four‐step transformation involves a rhodium carbene complex, a carbonyl ylide, and an isobenzopyrylium intermediate, the enantioselective reduction of which yields isochromanone derivatives in

  通过指挥棒：描述了使用四羧酸二（II）鎓和手性磷酸催化剂体系对羰基内酯形成/对映选择性还原序列进行单锅接力催化。四步转化涉及铑卡宾络合物，羰基叶立德和异苯并吡啶中间体，对映体的还原反应可高产率，高选择性地生成异苯并二氢吡喃酮衍生物。