2-(5-chloro-2-hydroxyphenyl)acetonitrile | 1261585-14-1

• 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-(5-chloro-2-hydroxyphenyl)acetonitrile
• 英文别名: 2-(5-Chloro-2-hydroxyphenyl)acetonitrile
• CAS: 1261585-14-1
• 化学式: C₈H₆ClNO
• 分子量: 167.595
• InChiKey: LRFHVSVDMITICK-UHFFFAOYSA-N

物化性质

• 沸点：
  318.7±27.0 °C(Predicted)
• 密度：
  1.329±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  44
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(5-chloro-2-hydroxyphenyl)acetonitrile 、 2-溴-3-吡啶甲醛 在 caesium carbonate 作用下， 以 甲苯 为溶剂， 反应 48.0h， 以75%的产率得到8-chlorobenzo[6,7]oxepino[2,3-b]pyridine-6-carbonitrile
  参考文献：
  名称：

  One-Pot Transition-Metal-Free Synthesis of Dibenzo[b,f]oxepins from 2-Halobenzaldehydes

  摘要：

  A one-pot transition-metal-free, base-mediated synthesis of dibenzo[b,f]oxepins was developed. The reaction of 2-halobenzaldehydes with (2-hydroxyphenyl)acetonitriles proceeds via a sequential aldol condensation and intramolecular ether formation reaction in the presence of Cs2CO3 and molecular sieves in toluene.

  DOI：

  10.1021/ol302371s
• 作为产物：
  描述：

  5-氯代水杨醛 在 sodium tetrahydroborate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.17h， 生成 2-(5-chloro-2-hydroxyphenyl)acetonitrile
  参考文献：
  名称：

  One-Pot Transition-Metal-Free Synthesis of Dibenzo[b,f]oxepins from 2-Halobenzaldehydes

  摘要：

  A one-pot transition-metal-free, base-mediated synthesis of dibenzo[b,f]oxepins was developed. The reaction of 2-halobenzaldehydes with (2-hydroxyphenyl)acetonitriles proceeds via a sequential aldol condensation and intramolecular ether formation reaction in the presence of Cs2CO3 and molecular sieves in toluene.

  DOI：

  10.1021/ol302371s

文献信息

• Palladium-Catalyzed Reaction of Arylboronic Acids with Aliphatic Nitriles: Synthesis of Alkyl Aryl Ketones and 2-Arylbenzofurans
  作者：Miaochang Liu、Jiuxi Chen、Xingyong Wang、Xiaodong Wang、Jinchang Ding、Huayue Wu

  DOI：10.1055/s-0033-1338909

  日期：——

  yields under the standard conditions. An efficient palladium-catalyzed addition of arylboronic acids to aliphatic nitriles has been developed, providing a wide range of alkyl aryl ketones in moderate to excellent yields. It is noteworthy that sequential addition and intramolecular annulation reaction of 2-(2-hydroxyphenyl)acetonitriles with arylboronic acids are also conducted smoothly to afford 2-arylbenzofurans

  摘要 已经开发出一种有效的钯催化的芳基硼酸加成到脂肪族腈中的方法，可以以中等到极好的收率提供各种各样的烷基芳基酮。值得注意的是，在标准条件下2-（2-羟苯基）乙腈与芳基硼酸的顺次加成和分子内环化反应也能顺利进行，从而以高收率得到2-芳基苯并呋喃。 已经开发出一种有效的钯催化的芳基硼酸加成到脂肪族腈中的方法，可以以中等到极好的收率提供各种各样的烷基芳基酮。值得注意的是，在标准条件下2-（2-羟苯基）乙腈与芳基硼酸的顺次加成和分子内环化反应也能顺利进行，从而以高收率得到2-芳基苯并呋喃。
• Palladium-Catalyzed Addition of Potassium Aryltrifluoroborates to Aliphatic Nitriles: Synthesis of Alkyl Aryl Ketones, Diketone Compounds, and 2-Arylbenzo[<i>b</i>]furans
  作者：Xingyong Wang、Miaochang Liu、Long Xu、Qingzong Wang、Jiuxi Chen、Jinchang Ding、Huayue Wu

  DOI：10.1021/jo400433m

  日期：2013.6.7

  developed, leading to a wide range of alkyl aryl ketones with moderate to excellent yields. Moreover, several dinitriles (e.g., malononitrile, glutaronitrile, and adiponitrile) were applicable to this process for the construction of 1,3-, 1,5-, or 1,6-dicarbonyl compounds. The scope of the developed approach is successfully explored toward the one-step synthesis of 2-arylbenzo[b]furans via sequential

  已经开发了钯催化的芳基三氟硼酸钾加成到脂肪族腈中的方法，从而产生了范围广泛的烷基芳基酮，并具有中等至极好的收率。此外，几种二腈（例如丙二腈，戊二腈和己二腈）适用于该方法，用于构建1,3-，1,5-或1,6-二羰基化合物。通过顺序加成和分子内环化反应，一步一步合成2-芳基苯并[ b ]呋喃已成功探索了所开发方法的范围。该方法学接受了广泛的底物，并适用于文库合成。
• Palladium-catalyzed tandem reaction of 2-hydroxyarylacetonitriles with sodium sulfinates: one-pot synthesis of 2-arylbenzofurans
  作者：Jiuxi Chen、Jianjun Li、Weike Su

  DOI：10.1039/c4ob00575a

  日期：——

  Palladium-catalyzed desulfinative addition and intramolecular annulation tandem reactions of 2-hydroxyarylacetonitriles with sodium sulfinates for one-pot synthesis of 2-arylbenzofurans.

  钯催化的去硫酸盐加成和分子内环化串联反应，利用钠亚磺酸盐进行一锅合成2-芳基苯并呋喃化合物。
• Catalyst-free synthesis of benzofuran-fused pyrido[4,3-d]pyrimidines from 2-(2-hydroxyaryl)acetonitrile and 4,6-dichloropyrimidine-5-carbaldehyde through domino condensation reactions
  作者：Bo Li、Zhizhou Yue、Haoyue Xiang、Linlin Lv、Shanshan Song、Zehong Miao、Chunhao Yang

  DOI：10.1039/c3ra44828b

  日期：——

  A rapid, one-pot, catalyst-free approach to novel benzofuran-fused pyrido[4,3-d]pyrimidines with good antitumor activities via a cascade SNAr/cyclization/condensation reaction through 2-(2-hydroxyphenyl)acetonitriles and 4,6-dichloropyrimidine-5-carbaldehyde was developed.

  一种快速，一锅煮，不含催化剂的方法来新颖苯并呋喃稠合的吡啶并[4,3- d ]具有良好的抗肿瘤活性的嘧啶经由级联小号Ñ的Ar /环化/缩合反应通过2-（2-羟基苯基）乙腈和开发了4，6-二氯嘧啶-5-甲醛。
• One-Pot Transition-Metal-Free Synthesis of Dibenzo[<i>b</i>,<i>f</i>]oxepins from 2-Halobenzaldehydes
  作者：Young Lok Choi、Hye Sun Lim、Hwan Jung Lim、Jung-Nyoung Heo

  DOI：10.1021/ol302371s

  日期：2012.10.5

  A one-pot transition-metal-free, base-mediated synthesis of dibenzo[b,f]oxepins was developed. The reaction of 2-halobenzaldehydes with (2-hydroxyphenyl)acetonitriles proceeds via a sequential aldol condensation and intramolecular ether formation reaction in the presence of Cs2CO3 and molecular sieves in toluene.