2,3-dihydro-2,2-dimethyl-1,5-benzothiazepin-4(5H)-one | 40334-89-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并硫氮卓类
• 英文名称: 2,3-dihydro-2,2-dimethyl-1,5-benzothiazepin-4(5H)-one
• 英文别名: 2,2-dimethyl-3,5-dihydro-1,5-benzothiazepin-4-one
• CAS: 40334-89-2
• 化学式: C₁₁H₁₃NOS
• mdl: MFCD00208281
• 分子量: 207.296
• InChiKey: CJNGOGZCBDLPPB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,3-dihydro-2,2-dimethyl-1,5-benzothiazepin-4(5H)-one 在 劳森试剂 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以84%的产率得到2,2-Dimethyl-2,3-dihydro-5H-benzo[b][1,4]thiazepine-4-thione
  参考文献：
  名称：

  Oxazep​​ines 和 Thiazepines，XXV：2,3-Dihydro-1,5-benzothiazepine-4 (5H) -ones 的化学转化

  摘要：

  2,3 - 二氢 - 1,5 - 苯并噻嗪 - 4 (5H) - 硫酮 13-22 通过适当的 2,3 - 二氢 - 1,5 - 苯并噻嗪 - 4 (5H) - 酮与劳森试剂反应制备. N-酰基（23-25）和N-烷基（26-28）衍生物也已合成。用3-氯过氧苯甲酸氧化得到亚砜29-32，以H2O2为氧化剂得到砜33-40。

  DOI：

  10.1002/ardp.19923251108
• 作为产物：
  描述：

  2-氨基苯硫醇 以55%的产率得到
  参考文献：
  名称：

  BALASUBRAMANIYAN, V.;BALASUBRAMANIYAN, P.;SHAIKH, A. S., TETRAHEDRON, 1986, 42, N 10, 2731-2738

  摘要：

  DOI：

文献信息

• Reactions of o-aminothiophenol withαβ-unsaturated dicarbonyl systems. Facile synthesis of benzothiazines and benzothiazepines
  作者：V. Balasubramaniyan、P. Balasubramaniyan、A.S. Shaikh

  DOI：10.1016/s0040-4020(01)90560-5

  日期：1986.1
• Spectroscopic and mass spectral investigation of some dihydro- and tetrahydro-1,5-benzodiazepines and thiazepines
  作者：P.W.W. Hunter、G.A. Webb

  DOI：10.1016/s0040-4020(01)93621-x

  日期：1972.1
• N-Heteroaryl glycinamides and glycinamines as potent NPY5 antagonists
  作者：Lingyun Wu、Kai Lu、Mahesh Desai、Mathivanan Packiarajan、Amita Joshi、Mohammad R. Marzabadi、Vrej Jubian、Kim Andersen、Gamini Chandrasena、Noel J. Boyle、Mary W. Walker

  DOI：10.1016/j.bmcl.2011.06.078

  日期：2011.9

  Subtype specific ligands are needed to evaluate the therapeutic potential of modulating the brain's neuropeptide Y system. The benzothiazepine glycinamide 1a was identified as an NPY5 antagonist lead. While having acceptable solubility, the compound was found to suffer from high clearance and poor exposure. Optimization efforts are described targeting improvements in potency, microsomal stability, and PK properties. The low microsomal stability and poor PK properties were addressed through the optimization of the sulfonyl urea and replacement of the benzothiazepinone with other N-heteroaryl glycinamides. For example, the analogous benzoxazine glycinamide 2e has improvements in both affinity (human Y5 K-i 4 nM vs 1a 27 nM) and microsomal stability (human CLint 2.5 L/min vs 1a 35 L/min). However the brain penetration (B/P 43/430 nM at 10 mg/kg PO) remained an unresolved issue. Further optimization by decreasing the hydrogen bond donating properties and PSA provided potent and brain penetrant NPY5 antagonists such as 5f (human Y5 K-i 9 nM, B/P 520/840 nM 10 mg/kg PO). (C) 2011 Elsevier Ltd. All rights reserved.
• Oxazepines and Thiazepines, 36. Diastereoselective Sulfoxidation of 2,3-Dihydro-1,5-benzothiazepin-4(5H)-ones by Dimethyldioxirane
  作者：Tamás Patonay、Waldemar Adam、József Jekö、Katalin E. Kövér、Albert Lévai、Márta Németh、Karl Peters

  DOI：10.3987/com-98-8353

  日期：——

  The highly chemoselective dimethyldioxirane oxidation of 2-substituted 2,3-dihydro-1,5-benzothiazepin-4(5H)-one (1) allows the synthesis of the corresponding sulfoxides (2) or sulfones (3) in good yields. The relative stereochemistry of the sulfoxides has been unequivocally determined by X-Ray and NMR methods. The high trans diastereoselectivity can be explained on the basis of steric control.
• Verfahren zur Kernchlorierung von aromatischen Kohlenwasserstoffen
  申请人：BAYER AG

  公开号：EP0292824B1

  公开（公告）日：1990-08-01