2-Hydroxymethyl-2-propyl-pentanal

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-Hydroxymethyl-2-propyl-pentanal
• 英文别名: 2-(Hydroxymethyl)-2-propylpentanal；2-(hydroxymethyl)-2-propylpentanal
• 化学式: C₉H₁₈O₂
• 分子量: 158.241
• InChiKey: IMUHWCSBGMZCGT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 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-Hydroxymethyl-2-propyl-pentanal 在 palladium on activated charcoal 氢气 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 20.0 ℃ 、689.47 kPa 条件下， 反应 18.0h， 生成
  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 、 2-丙基戊醛 生成 2-Hydroxymethyl-2-propyl-pentanal
  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

• 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）。
• 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