methyl 7-bromo-5-hydroxy-1-[(4-methylphenyl)sulfonyl]-2,3-dihydro-1H-1-benzazepine-4-carboxylate | 313739-35-4

• 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: methyl 7-bromo-5-hydroxy-1-[(4-methylphenyl)sulfonyl]-2,3-dihydro-1H-1-benzazepine-4-carboxylate
• 英文别名: methyl 7-bromo-5-hydroxy-1-tosyl-2,3-dihydro-1H-1-benzazepine-4-carboxylate；Methyl 7-bromo-5-hydroxy-1-(4-methylphenyl)sulfonyl-2,3-dihydro-1-benzazepine-4-carboxylate
• CAS: 313739-35-4
• 化学式: C₁₉H₁₈BrNO₅S
• 分子量: 452.326
• InChiKey: ZFCGVCOMOBBKSH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  92.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 7-bromo-5-hydroxy-1-[(4-methylphenyl)sulfonyl]-2,3-dihydro-1H-1-benzazepine-4-carboxylate 在 sodium tetrahydroborate 、 硫酸 、 水 作用下， 以 四氢呋喃 、 溶剂黄146 为溶剂， 反应 13.0h， 生成 7-溴-2,3-二氢-1H-苯并[B]氮杂-4-羧酸
  参考文献：
  名称：

  Preparation of a 1-Unsubstituted 2,3-Dihydro-1-benzazepine Derivative

  摘要：

  We developed a three-step method of producing a 1-unsubstituted-2,3-dihydro-1-benzazepine derivative (2) from 11. The alkylation of 9, obtained from 11, and the subsequent intramolecular condensation of 12 in dialkyl carbonate with a metal alcoholate were conducted in one pot to afford 1-benzazepine (13) in good yield. 13 was then hydrolyzed to give 2 in 48% overall yield from 11. Furthermore, we synthesized the orally active CCR5 antagonist intermediate 18 from 2.

  DOI：

  10.3987/com-07-11025
• 作为产物：
  描述：

  methyl 5-bromo-2-{(4-methoxy-4-oxobutyl)[(4-methylphenyl)sulfonyl]amino}benzoate 在 sodium methylate 、 碳酸二甲酯 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以95%的产率得到methyl 7-bromo-5-hydroxy-1-[(4-methylphenyl)sulfonyl]-2,3-dihydro-1H-1-benzazepine-4-carboxylate
  参考文献：
  名称：

  Preparation of a 1-Unsubstituted 2,3-Dihydro-1-benzazepine Derivative

  摘要：

  We developed a three-step method of producing a 1-unsubstituted-2,3-dihydro-1-benzazepine derivative (2) from 11. The alkylation of 9, obtained from 11, and the subsequent intramolecular condensation of 12 in dialkyl carbonate with a metal alcoholate were conducted in one pot to afford 1-benzazepine (13) in good yield. 13 was then hydrolyzed to give 2 in 48% overall yield from 11. Furthermore, we synthesized the orally active CCR5 antagonist intermediate 18 from 2.

  DOI：

  10.3987/com-07-11025

文献信息

• BENZAZEPINE DERIVATIVES, PROCESS FOR THE PREPARATION OF THE SAME AND USES THEREOF
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP1186604A1

  公开（公告）日：2002-03-13

  Compounds of the general formula (I): or salts thereof, which exhibit CCR5 antagonism and exert preventive and therapeutic effects against HIV infections: wherein R1 is a 5- to 6-membered aromatic ring which bears a substituent represented by the general formula: R-Z1-X-Z2- (wherein R1 is hydrogen or optionally substituted hydrocarbyl; X is optionally substituted alkylene; and Z1 and Z2 are each a heteroatom) and may be further substituted, with R being optionally bonded to the aromatic ring to form another ring; Y is optionally substituted imino; and R2 and R3 are each optionally substituted aliphatic hydrocarbyl or an optionally substituted hetero-alicyclic group.

  具有一般公式(I)的化合物： 或其盐，具有CCR5拮抗作用，并对HIV感染具有预防和治疗作用：其中R1是一个5至6成员的芳香环，带有一个由一般公式表示的取代基：R-Z1-X-Z2-（其中R1是氢或可选地取代的碳氢基；X是可选地取代的亚烷基；Z1和Z2都是杂原子）并可进一步取代，R可可选地与芳香环结合形成另一个环；Y是可选地取代的亚胺；R2和R3各自是可选地取代的脂肪族碳氢化合物或一个可选地取代的杂环脂肪族基团。
• US6936602B1
  申请人：——

  公开号：US6936602B1

  公开（公告）日：2005-08-30
• Preparation of a 1-Unsubstituted 2,3-Dihydro-1-benzazepine Derivative
  作者：Atsuko Nishiguchi、Tomomi Ikemoto、Tatsuya Ito、Shotaro Miura、Kiminori Tomimatsu

  DOI：10.3987/com-07-11025

  日期：——

  We developed a three-step method of producing a 1-unsubstituted-2,3-dihydro-1-benzazepine derivative (2) from 11. The alkylation of 9, obtained from 11, and the subsequent intramolecular condensation of 12 in dialkyl carbonate with a metal alcoholate were conducted in one pot to afford 1-benzazepine (13) in good yield. 13 was then hydrolyzed to give 2 in 48% overall yield from 11. Furthermore, we synthesized the orally active CCR5 antagonist intermediate 18 from 2.