己醛,2-[[[2-(溴甲基)-4-氟苯基]硫代]甲基]-2-丁基- | 197378-18-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 己醛,2-[[[2-(溴甲基)-4-氟苯基]硫代]甲基]-2-丁基-
• 英文名称: 2-[[[2-(bromomethyl)-4-fluorophenyl]thio]methyl]-2-butylhexanal
• 英文别名: 2-(2-butyl-2-formylhexylthio)-5-fluoro-benzyl bromide；2-[[2-(Bromomethyl)-4-fluorophenyl]sulfanylmethyl]-2-butylhexanal
• CAS: 197378-18-0
• 化学式: C₁₈H₂₆BrFOS
• 分子量: 389.372
• InChiKey: WPGVGXHYFNWCKI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  22
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  3

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	2-(2-butyl-2-formylhexylthio)-5-fluoro-benzylalcohol	197378-16-8	C18H27FO2S	326.476
  ——	2-(2-butyl-2-formylhexylthio)-5-fluoro-benzaldehyde	197378-15-7	C18H25FO2S	324.46

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	2-[[[2-(bromomethyl)-4-fluorophenyl]sulfonyl]methyl]-2-butylhexanal	197378-13-5	C18H26BrFO3S	421.371

反应信息

• 作为反应物：
  描述：

  己醛,2-[[[2-(溴甲基)-4-氟苯基]硫代]甲基]-2-丁基- 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 5.17h， 以98%的产率得到2-[[[2-(bromomethyl)-4-fluorophenyl]sulfonyl]methyl]-2-butylhexanal
  参考文献：
  名称：

  Discovery of Potent, Nonsystemic Apical Sodium-Codependent Bile Acid Transporter Inhibitors (Part 2)

  摘要：

  In the preceding paper several compounds were reported as potent apical. sodium-codependent bile acid transporter (ASBT) inhibitors. Since the primary site for active bile acid reabsorption is via ASBT, which is localized on the luminal surface of the distal ileum, we reasoned that a nonsystemic inhibitor would be desirable to minimize or eliminate potential systemic side effects of an absorbed drug. To ensure bioequivalency and product stability, it was also essential that we identify a nonhygroscopic inhibitor in its most stable crystalline form. A series of benzothiepines were prepared to refine the structure-activity relationship of the substituted phenyl ring at the 5-position of benzothiepine ring and to identify potent, crystalline, nonhygroscopic, and efficacious ASBT inhibitors with low systemic exposure.

  DOI：

  10.1021/jm0402162
• 作为产物：
  描述：

  2,5-二氟苯甲醛 在 lithium sulfide 、 bromotriphenylphosphonium bromide 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.5h， 生成 己醛,2-[[[2-(溴甲基)-4-氟苯基]硫代]甲基]-2-丁基-
  参考文献：
  名称：

  Discovery of Potent, Nonsystemic Apical Sodium-Codependent Bile Acid Transporter Inhibitors (Part 2)

  摘要：

  In the preceding paper several compounds were reported as potent apical. sodium-codependent bile acid transporter (ASBT) inhibitors. Since the primary site for active bile acid reabsorption is via ASBT, which is localized on the luminal surface of the distal ileum, we reasoned that a nonsystemic inhibitor would be desirable to minimize or eliminate potential systemic side effects of an absorbed drug. To ensure bioequivalency and product stability, it was also essential that we identify a nonhygroscopic inhibitor in its most stable crystalline form. A series of benzothiepines were prepared to refine the structure-activity relationship of the substituted phenyl ring at the 5-position of benzothiepine ring and to identify potent, crystalline, nonhygroscopic, and efficacious ASBT inhibitors with low systemic exposure.

  DOI：

  10.1021/jm0402162

文献信息

• Novel benzothiazepine and bensothiepine compounds
  申请人：Sasahara Takehiko

  公开号：US20070190041A1

  公开（公告）日：2007-08-16

  A pharmaceutical useful as a therapeutic agent and a preventive agent for hyperlipemia, and a pharmaceutical useful as a therapeutic agent and a preventive agent for hepatic disorders associated with cholestasis, particularly, primary biliary cirrhosis and primary sclerosing cholangitis, and a pharmaceutical useful as a therapeutic agent and a preventive agent for obesity, fatty liver and steatohepatitis are provided. A benzothiazepine or benzothiepine compound represented by the following formula (1A) having a thioamide bond and a quaternary ammonium substitutent:

  提供了一种药物，可用作治疗和预防高脂血症的治疗剂和预防剂，以及一种药物，可用作治疗和预防与胆汁淤积有关的肝脏疾病，特别是原发性胆汁性肝硬化和原发性硬化性胆管炎的治疗剂和预防剂，以及一种药物，可用作治疗和预防肥胖症、脂肪肝和脂肪性肝炎的治疗剂和预防剂。化合物的苯并噻吩或苯并噻环代表如下式（1A），具有硫酰胺键和季铵取代基：
• A Highly Enantioselective Benzothiepine Synthesis
  作者：Ching-Cheng Wang、James J. Li、Horng-Chih Huang、Len F. Lee、David B. Reitz

  DOI：10.1021/jo991786q

  日期：2000.5.1

  A highly enantioselective synthesis of benzothiepine 1a has been accomplished via an enantioenriched sulfoxide intermediate obtained by asymmetric oxidation with a chiral oxaziridine in 89:11 er. The key step is a thermodynamically controlled asymmetric cyclization reaction that produces two new stereogenic centers. The (4R,5R) isomer 1a was obtained in 98:2 er.

  苯并噻庚因1a的高度对映选择性合成是通过在89:11 er中通过手性恶唑烷进行不对称氧化而获得的对映体富集的亚砜中间体。关键步骤是热力学控制的不对称环化反应，产生两个新的立体异构中心。（4R，5R）异构体1a以98∶2 er获得。
• NOVEL BENZOTHIAZEPINE AND BENZOTHIEPINE COMPOUNDS
  申请人：Asahi Kasei Pharma Corporation

  公开号：EP1719768B1

  公开（公告）日：2012-04-25
• US7973030B2
  申请人：——

  公开号：US7973030B2

  公开（公告）日：2011-07-05
• Discovery of Potent, Nonsystemic Apical Sodium-Codependent Bile Acid Transporter Inhibitors (Part 2)
  作者：Horng-Chih Huang、Samuel J. Tremont、Len F. Lee、Bradley T. Keller、Andrew J. Carpenter、Ching-Cheng Wang、Shyamal C. Banerjee、Scott R. Both、Theresa Fletcher、Danny J. Garland、Wei Huang、Claude Jones、Kevin J. Koeller、Steve A. Kolodziej、James Li、Robert E. Manning、Matthew W. Mahoney、Raymond E. Miller、Deborah A. Mischke、Nigam P. Rath、Emily J. Reinhard、Michael B. Tollefson、William F. Vernier、Grace M. Wagner、Steve R. Rapp、Judy Beaudry、Kevin Glenn、Karen Regina、Joe R. Schuh、Mark E. Smith、Jay S. Trivedi、David B. Reitz

  DOI：10.1021/jm0402162

  日期：2005.9.1

  In the preceding paper several compounds were reported as potent apical. sodium-codependent bile acid transporter (ASBT) inhibitors. Since the primary site for active bile acid reabsorption is via ASBT, which is localized on the luminal surface of the distal ileum, we reasoned that a nonsystemic inhibitor would be desirable to minimize or eliminate potential systemic side effects of an absorbed drug. To ensure bioequivalency and product stability, it was also essential that we identify a nonhygroscopic inhibitor in its most stable crystalline form. A series of benzothiepines were prepared to refine the structure-activity relationship of the substituted phenyl ring at the 5-position of benzothiepine ring and to identify potent, crystalline, nonhygroscopic, and efficacious ASBT inhibitors with low systemic exposure.