N-{4-Chloro-2-[hydroxy(phenyl)methyl]phenyl}-4-methylbenzamide | 857816-66-1

• 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: N-{4-Chloro-2-[hydroxy(phenyl)methyl]phenyl}-4-methylbenzamide
• 英文别名: N-[4-chloro-2-[hydroxy(phenyl)methyl]phenyl]-4-methylbenzamide
• CAS: 857816-66-1
• 化学式: C₂₁H₁₈ClNO₂
• 分子量: 351.832
• InChiKey: YQTKUSALRWBQOF-UHFFFAOYSA-N

物化性质

• 熔点：
  170 °C(Solv: chloroform (67-66-3))
• 沸点：
  460.5±45.0 °C(Predicted)
• 密度：
  1.283±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-{4-Chloro-2-[hydroxy(phenyl)methyl]phenyl}-4-methylbenzamide 在 4,4'-二氨基二苯乙烯-2,2'-二磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以50%的产率得到6-chloro-4-phenyl-2-p-tolyl-4H-3,1-benzoxazine
  参考文献：
  名称：

  Synthesis of 4H-3,1-Benzoxazines by the Reaction of o-(N-Acylamino)benzyl Alcohols with DAST

  摘要：

  The treatment of o-(N-acylamino)benzyl alcohols (1) with DAST afforded the dehydrative cyclization product, 4H-3,1-benzoxazines (4) and the hydroxy replacement product, o-(N-acylamino)benzyl fluorides (5). The yields of benzoxazines (4) and fluorides (5) depend on the substituents at alpha-position and acyl groups. The treatment of alpha,alpha-diaryl-o-(N-acylamino)benzyl alcohols (1a-c) with DAST yielded benzoxazines (4a-c) exclusively, while that of alpha-monosubstituted o-(N-acylamino)benzyl alcohols (Id-k) with DAST yielded benzoxazines (4d-k) and fluorides (5d-k). In the reaction of o-(N-acylamino)benzyl alcohol (11) with DAST, the formation of fluoride (51) became predominant and that of benzoxazine (41) was suppressed almost completely.

  DOI：

  10.3987/com-05-s(t)22
• 作为产物：
  描述：

  N-(2-benzoyl-4-chlorophenyl)-4-methylbenzamide 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 30.0h， 以81%的产率得到N-{4-Chloro-2-[hydroxy(phenyl)methyl]phenyl}-4-methylbenzamide
  参考文献：
  名称：

  Hatim, Jaywant Govind; Joshi, Vidya, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2004, vol. 43, # 12, p. 2689 - 2695

  摘要：

  DOI：

文献信息

• Hatim, Jaywant Govind; Joshi, Vidya, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2004, vol. 43, # 12, p. 2689 - 2695
  作者：Hatim, Jaywant Govind、Joshi, Vidya

  DOI：——

  日期：——
• Synthesis of 4H-3,1-Benzoxazines by the Reaction of o-(N-Acylamino)benzyl Alcohols with DAST
  作者：Takehiko Nishio、Yukiko Kurokawa、Yoshiya Narasaki、Tatsuhiro Tokunaga

  DOI：10.3987/com-05-s(t)22

  日期：——

  The treatment of o-(N-acylamino)benzyl alcohols (1) with DAST afforded the dehydrative cyclization product, 4H-3,1-benzoxazines (4) and the hydroxy replacement product, o-(N-acylamino)benzyl fluorides (5). The yields of benzoxazines (4) and fluorides (5) depend on the substituents at alpha-position and acyl groups. The treatment of alpha,alpha-diaryl-o-(N-acylamino)benzyl alcohols (1a-c) with DAST yielded benzoxazines (4a-c) exclusively, while that of alpha-monosubstituted o-(N-acylamino)benzyl alcohols (Id-k) with DAST yielded benzoxazines (4d-k) and fluorides (5d-k). In the reaction of o-(N-acylamino)benzyl alcohol (11) with DAST, the formation of fluoride (51) became predominant and that of benzoxazine (41) was suppressed almost completely.