2-butyl-2-(hydroxymethyl)hexanal | 864350-12-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-butyl-2-(hydroxymethyl)hexanal
• CAS: 864350-12-9
• 化学式: C₁₁H₂₂O₂
• 分子量: 186.294
• InChiKey: FZUPLNMJHOWMKW-UHFFFAOYSA-N

物化性质

• 沸点：
  273.4±23.0 °C(Predicted)
• 密度：
  0.908±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-butyl-2-(hydroxymethyl)hexanal 在 palladium on activated charcoal potassium tert-butylate 、 氢气 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 20.0 ℃ 、689.47 kPa 条件下， 反应 18.0h， 生成 (+/-)-(4R,5R)-7-amino-3,3-dibutyl-2,3,4,5-tetrahydro-5-phenyl-1-benzothiepin-4-ol 1,1-dioxide
  参考文献：
  名称：

  Discovery of Potent, Nonsystemic Apical Sodium-Codependent Bile Acid Transporter Inhibitors (Part 1)

  摘要：

  Elevated plasma levels of low-density lipoprotein (LDL) cholesterol are a major risk factor for atherosclerosis leading to coronary artery disease (CAD), which remains the main cause of mortality in Western society. We believe that by preventing the reabsorption of bile acids, a minimally absorbed apical sodium-codependent bile acid transporter (ASBT) inhibitor would lower the serum cholesterol without the potential systemic side effects of an absorbed drug. A series of novel benzothiepines (3R,3R'-2,3,4,5-tetrahydro-5-aryl-l-benzothiepin-4-ol 1,1-dioxides) were synthesized and tested for their ability to inhibit the apical sodium dependent bile acid transport (ASBT)-mediated uptake of [C-14]taurocholate (TC) in H14 cells. A 3R,4.R,5R13S,4S,5S racemate was found to have greater potency than the other three possible racemates. Addition of electron-donating groups such as a dimethylamino substituent at the 7 position greatly enhanced potency, and incorporation of a long-chain quaternary ammonium substituent on the 5-phenyl ring was useful in minimizing systemic exposure of this locally active ASBT inhibitor while also increasing water solubility and maintaining potency. The reported results describe the synthesis and SAR development of this benzothiepine class of ASBT inhibitors resulting in an 6000-fold improvement in ASBT inhibition with desired minimal systemic exposure of this locally acting drug candidate.

  DOI：

  10.1021/jm040215+
• 作为产物：
  描述：

  聚合甲醛 、 二-正丁基乙醛 生成 2-butyl-2-(hydroxymethyl)hexanal
  参考文献：
  名称：

  Discovery of Potent, Nonsystemic Apical Sodium-Codependent Bile Acid Transporter Inhibitors (Part 1)

  摘要：

  Elevated plasma levels of low-density lipoprotein (LDL) cholesterol are a major risk factor for atherosclerosis leading to coronary artery disease (CAD), which remains the main cause of mortality in Western society. We believe that by preventing the reabsorption of bile acids, a minimally absorbed apical sodium-codependent bile acid transporter (ASBT) inhibitor would lower the serum cholesterol without the potential systemic side effects of an absorbed drug. A series of novel benzothiepines (3R,3R'-2,3,4,5-tetrahydro-5-aryl-l-benzothiepin-4-ol 1,1-dioxides) were synthesized and tested for their ability to inhibit the apical sodium dependent bile acid transport (ASBT)-mediated uptake of [C-14]taurocholate (TC) in H14 cells. A 3R,4.R,5R13S,4S,5S racemate was found to have greater potency than the other three possible racemates. Addition of electron-donating groups such as a dimethylamino substituent at the 7 position greatly enhanced potency, and incorporation of a long-chain quaternary ammonium substituent on the 5-phenyl ring was useful in minimizing systemic exposure of this locally active ASBT inhibitor while also increasing water solubility and maintaining potency. The reported results describe the synthesis and SAR development of this benzothiepine class of ASBT inhibitors resulting in an 6000-fold improvement in ASBT inhibition with desired minimal systemic exposure of this locally acting drug candidate.

  DOI：

  10.1021/jm040215+

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：
• Benzothiazepine and benzothiepine compounds
  申请人：Asahi Kasei Pharma Corporation

  公开号：US07973030B2

  公开（公告）日：2011-07-05

  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:

  提供一种作为治疗剂和预防剂用于高脂血症的药物，以及一种作为治疗剂和预防剂用于与胆汁淤积相关的肝疾病，特别是原发性胆汁性肝硬化和原发性硬化性胆管炎的药物，以及一种作为治疗剂和预防剂用于肥胖症、脂肪肝和脂肪性肝炎的药物。该药物是一种具有硫酰胺键和季铵取代基的苯并噻吩或苯并噻烯化合物，其化学式为（1A）。
• METHOD FOR PREPARING CYCLIC ACETAL COMPOUND
  申请人：Mitsubishi Gas Chemical Company, Inc.

  公开号：EP3466941A1

  公开（公告）日：2019-04-10

  A process for producing a cyclic acetal compound represented by the following general formula (3), comprising a step of subjecting a compound A represented by the following general formula (1) and a compound B represented by the following general formula (2) to cyclodehydration reaction in a system comprising a mixture of the compound A and water, the mixture comprising 20% by mass or more of water based on the total amount of the compound A and water, an acid catalyst and the compound B, wherein in the step, water contained in the mixture and water formed by the cyclodehydration reaction are removed from the system at the same time. (In the formulas, R1, R2, R3 and R4 each independently represent a straight-chain or branched alkyl group having 1 to 6 carbon atoms or a hydroxymethyl group.)

  一种生产由以下通式(3)表示的环缩醛化合物的工艺，包括以下步骤： 在由化合物 A 和水的混合物组成的体系中，使由以下通式(1)表示的化合物 A 和由以下通式(2)表示的化合物 B 进行环脱水反应、在该步骤中，混合物中含有的水和通过环脱水反应生成的水同时从系统中去除。 (在公式中，R1、R2、R3 和 R4 各自独立地代表具有 1 至 6 个碳原子的直链或支链烷基或羟甲基）。
• NOVEL BENZOTHIAZEPINE AND BENZOTHIEPINE COMPOUNDS
  申请人：Asahi Kasei Pharma Corporation

  公开号：EP1719768B1

  公开（公告）日：2012-04-25
• PROCESS FOR PRODUCING CYCLIC ACETAL COMPOUND
  申请人：Mitsubishi Gas Chemical Company, Inc.

  公开号：EP3466941B1

  公开（公告）日：2020-08-05