α-(3-chloro-4-fluoroaniline)-2-cresol | 329779-41-1

• 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: α-(3-chloro-4-fluoroaniline)-2-cresol
• 英文别名: 2-(3-chloro-4-fluorophenylamino)methylphenol；2-{[(3-Chloro-4-fluorophenyl)amino]methyl}phenol；2-[(3-chloro-4-fluoroanilino)methyl]phenol
• CAS: 329779-41-1
• 化学式: C₁₃H₁₁ClFNO
• mdl: MFCD02105874
• 分子量: 251.688
• InChiKey: VAENDKVBNUCVBT-UHFFFAOYSA-N

物化性质

• 沸点：
  397.0±37.0 °C(Predicted)
• 密度：
  1.366±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.076
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  α-(3-chloro-4-fluoroaniline)-2-cresol 在 4-二甲氨基吡啶 、 三乙胺 、 三氯氧磷 作用下， 以 甲苯 为溶剂， 生成 2-chloro-3,4-dihydro-3-(3'-chloro-4'-fluorophenyl)-2H-[1,3,2]oxazaphosphorin 2-oxide
  参考文献：
  名称：

  Kiran; Kasthuraiah; Nagaraju, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2005, vol. 44, # 10, p. 2171 - 2177

  摘要：

  DOI：
• 作为产物：
  描述：

  3-氯-4-氟苯胺 、 水杨醛 在 溶剂黄146 、 sodium tetrahydroborate 作用下， 以 乙腈 为溶剂， 反应 2.5h， 生成 α-(3-chloro-4-fluoroaniline)-2-cresol
  参考文献：
  名称：

  邻氨基-C（sp 2）–H官能化合成叔胺的无金属二芳基二胺，合成二苯并x氮平和-ones

  摘要：

  利用苯乙酸碘（III）介导的叔胺与适当取代的邻羟基苄基和苯基基团的蛋白反应，可促进邻-C（sp 2）-H官能化，从而提供二芳基醚。原位产生的所得二芳基醚中邻-CHO和仲胺官能团的存在被用于合成二苯并x氮杂和二苯并a氮杂酮。温和的条件和相对较宽的底物范围以及二芳基醚进一步多样化的潜力是该方法的重点。

  DOI：

  10.1021/acs.orglett.7b03328

文献信息

• Synthesis and anticancer activity of new class of bisphosphonates/phosphanamidates
  作者：Y.B. Kiran、C. Devendranath Reddy、D. Gunasekar、C. Suresh Reddy、Annette Leon、Luiz C.A. Barbosa

  DOI：10.1016/j.ejmech.2007.05.014

  日期：2008.4

  Novel bis-heterocyclic bisphosphonates/phosphonamidates were synthesized utilizing the Pudovick reaction. The employment Of Nb2O5 as catalyst was found to increase the yields and purity of the bisbenzoxazaphosphine derivatives (13a-h). Their anticancer activity studies in vitro, on three human tumor cell lines NCI-H460 (lung large cell), MCF-7 (breast adenocarcinoma), and SF-268 (central nervous system glioblastoma), showed that bis-[3-(3-chloro-4-fluorophenyl)-2-oxo-3,4-dihydro-2H-2 lambda(5)-benzo[e][1,3,2]oxazaphosphinin-2-yl]arylmethanes (13a-h) and [(4-chlorophenyl)-(hydroxyamidophosphinoyl)-methyl]phosphonic acid (14) exhibited significant anticancer activity. (c) 2007 Elsevier Masson SAS. All rights reserved.
• Synthesis of [3-(3-Chloro-4-fluorophenyl)-2-oxo-3,4-dihydro-2<i>H</i>-2λ⁵- benzo[<i>e</i>][1,3,2]oxazaphosphinin-2-yl]-(aryl/alkyl) Methanols and Their Bioactivity on Sugarcane Smut
  作者：Y. B. Kiran、P. Vasu Govardhana Reddy、C. Devendranath Reddy、D. Gunasekar、N. P. Eswara Reddy

  DOI：10.1021/jf070850z

  日期：2007.8.1

  Synthesis of some new substituted [3-(3-chloro-4-fluorophenyl)-2-oxo-3,4-dihydro-2H-2 lambda(5)-benzo[e][1,3,2]oxazaphosphinin-2-yl]-(aryl/alkyl)methanols (7a-k) based on the Pudovick reaction was accomplished in the presence of niobium pentoxide (Nb2O5) without using an external chiral ligand. Nb2O5 appears to form the metal complex intermediate catalyst system (6) by reacting with 3-(3-chloro-4-fluoro-phenyl)-3,4-dihydrobenzo[e][1,3,2]oxazaphosphinine-2-oxide (4), which not only directs the Pudovick addition reactions of aldehyde but also increases the yields and purity of the products. These compounds exhibited a lethal effect on whip smut of sugarcane and were degraded in the environment in the presence of bacteria and fungi to nontoxic phosphate residues that act as possible plant nutrients. Thus, a new class of benzooxazaphosphininyl methanol derivatives that act in synergy both as antipathogens and as plant nutrients in the environment have been discovered.
• Kiran; Kasthuraiah; Nagaraju, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2005, vol. 44, # 10, p. 2171 - 2177
  作者：Kiran、Kasthuraiah、Nagaraju、Gunasekar、Madhu Babu、Devendranath Reddy

  DOI：——

  日期：——
• Metal-Free Diaryl Etherification of Tertiary Amines by <i>Ortho</i>-C(sp²)–H Functionalization for Synthesis of Dibenzoxazepines and -ones
  作者：Vellekkatt Jamsheena、Chikkagundagal K. Mahesha、M. Nibin Joy、Ravi S. Lankalapalli

  DOI：10.1021/acs.orglett.7b03328

  日期：2017.12.15

  A phenyliodine(III) diacetate mediated umpolung reactivity of the tertiary amines with suitably substituted o-hydroxybenzyl and phenyl groups is exploited to facilitate o-C(sp2)–H functionalization to afford diaryl ethers. The presence of an o-CHO and secondary amine functionalities in the resulting diaryl ether, generated in situ, were utilized for synthesis of dibenzoxazepines and dibenzoxazepinones

  利用苯乙酸碘（III）介导的叔胺与适当取代的邻羟基苄基和苯基基团的蛋白反应，可促进邻-C（sp 2）-H官能化，从而提供二芳基醚。原位产生的所得二芳基醚中邻-CHO和仲胺官能团的存在被用于合成二苯并x氮杂和二苯并a氮杂酮。温和的条件和相对较宽的底物范围以及二芳基醚进一步多样化的潜力是该方法的重点。