N-octanoyl-3-amino-1,2-propanediol | 72809-04-2

• 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: N-octanoyl-3-amino-1,2-propanediol
• 英文别名: N-(2,3-dihydroxypropyl)octanamide
• CAS: 72809-04-2
• 化学式: C₁₁H₂₃NO₃
• 分子量: 217.309
• InChiKey: GXTDJFUXUPDWTH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-octanoyl-3-amino-1,2-propanediol 在 吡啶 、 甲醇 、 sodium hydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 28.0h， 生成 Phosphoric acid 2-bromo-ethyl ester 2-butoxy-3-octanoylamino-propyl ester
  参考文献：
  名称：

  Structure−Activity Relationship for Enhancement of Paracellular Permeability across Caco-2 Cell Monolayers by 3-Alkylamido-2-alkoxypropylphosphocholines

  摘要：

  Paracellular permeability enhancers have been used to improve the oral bioavailability of hydrophilic drugs; however, the mechanism of action of many enhancers is poorly understood. In this study, highly potent enhancers of paracellular permeability were identified in the 3-alkylamido-2-alkoxypropylphosphocholine series, and a structure-activity relationship was developed for enhancement of paracellular permeability across Caco-2 cell monolayers. Compounds with short (<5 carbons) hydrocarbon chains at both C-2 and C-3 were generally inactive. The potency exhibited a parabolic relationship with respect to the chain length at either C-2 or C-3. Linear molecules (i.e., compounds with a short hydrocarbon chain at C-2 or C-3 and a long hydrocarbon chain on C-3 or C-2, respectively) were more potent than the corresponding branched molecules with the same carbon load. The efficacy of 3-alkylamido2-alkoxypropylphosphocholines as enhancers of paracellular permeability was not dependent on their existence in micellar form or their ability to alter the fluidity of cell membrane. Previously, a correlation-between the potency of alkylphosphocholines as enhancers of paracellular permeability and the inhibitors of phospholipase C (PLC) was established in Madine Darby canine kidney (MDCK) cell monolayers. The potencies of selected 3-alkylamido-2-alkoxypropylphosphocholines as inhibitors of PLC and enhancers of paracellular permeability fit well into this correlation. Therefore, phosphocholines are likely to increase paracellular permeability by modulating the signal transduction pathway initiated by a PLC-catalyzed reaction rather than by physically altering the cell membrane.

  DOI：

  10.1021/jm020001x
• 作为产物：
  描述：

  3-氨基-1,2-丙二醇 、 辛酰氯 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以47%的产率得到N-octanoyl-3-amino-1,2-propanediol
  参考文献：
  名称：

  单酰基甘油作为跨膜Cl-阴离子转运蛋白。

  摘要：

  我们报告说两亲的天然产物，单酰基甘油1，作为跨膜Cl（-）/ NO（3）（-）阴离子转运蛋白。1，2-二醇基对于转运功能至关重要，因为二酰基甘油和三酰基甘油类似物不是阴离子转运蛋白。此外，将另一个氢键供体添加到甘油的头基和酰基尾的全氟化得到具有改进的Cl（-）膜运输性质的合成类似物。

  DOI：

  10.1039/c2cc18148g

文献信息

• One‐Step Biocatalytic Synthesis of Sustainable Surfactants by Selective Amide Bond Formation**
  作者：Max Lubberink、William Finnigan、Christian Schnepel、Christopher R. Baldwin、Nicholas J. Turner、Sabine L. Flitsch

  DOI：10.1002/anie.202205054

  日期：2022.7.25

  route to commercially important surfactants is presented. A truncated construct of carboxylic acid reductase (CARmm-A) catalyzes amide bond formation between fatty acids and amino alcohols with no esterification observed. The wide substrate scope of the enzyme, co-factor recycling, reaction engineering and up-scaling show the feasibility of this method for synthesis.

  提出了一种获得商业上重要的表面活性剂的酶促途径。截短的羧酸还原酶构建体 (CAR mm -A) 催化脂肪酸和氨基醇之间形成酰胺键，未观察到酯化反应。该酶的广泛底物范围、辅因子回收、反应工程和放大显示了该合成方法的可行性。
• SULFUR-CONTAINING SILANE, FILLED ELASTOMERIC COMPOSITIONS CONTAINING SAME AND ARTICLES MADE THEREFROM
  申请人：Momentive Performance Materials Inc.

  公开号：EP2310397A1

  公开（公告）日：2011-04-20
• Sulfur-Containing Silane, Filled Elastomeric Compositions Containing Same And Articles Made Therefrom
  申请人：Hwang Lesley

  公开号：US20110021692A1

  公开（公告）日：2011-01-27

  Sulfur-containing silanes described herein can serve as coupling agents for fillers in elastomer compositions used, for example, in tires, belts, hoses, shoe soles, seals, gaskets, and the like. The sulfur containing silanes advantageously reduce or eliminate the generation of volatile organic compounds (VOCs) during use.
• Structure−Activity Relationship for Enhancement of Paracellular Permeability across Caco-2 Cell Monolayers by 3-Alkylamido-2-alkoxypropylphosphocholines
  作者：Hui Ouyang、Susan L. Morris-Natschke、Khalid S. Ishaq、Peter Ward、Dongzhou Liu、Sarah Leonard、Dhiren R. Thakker

  DOI：10.1021/jm020001x

  日期：2002.6.1

  Paracellular permeability enhancers have been used to improve the oral bioavailability of hydrophilic drugs; however, the mechanism of action of many enhancers is poorly understood. In this study, highly potent enhancers of paracellular permeability were identified in the 3-alkylamido-2-alkoxypropylphosphocholine series, and a structure-activity relationship was developed for enhancement of paracellular permeability across Caco-2 cell monolayers. Compounds with short (<5 carbons) hydrocarbon chains at both C-2 and C-3 were generally inactive. The potency exhibited a parabolic relationship with respect to the chain length at either C-2 or C-3. Linear molecules (i.e., compounds with a short hydrocarbon chain at C-2 or C-3 and a long hydrocarbon chain on C-3 or C-2, respectively) were more potent than the corresponding branched molecules with the same carbon load. The efficacy of 3-alkylamido2-alkoxypropylphosphocholines as enhancers of paracellular permeability was not dependent on their existence in micellar form or their ability to alter the fluidity of cell membrane. Previously, a correlation-between the potency of alkylphosphocholines as enhancers of paracellular permeability and the inhibitors of phospholipase C (PLC) was established in Madine Darby canine kidney (MDCK) cell monolayers. The potencies of selected 3-alkylamido-2-alkoxypropylphosphocholines as inhibitors of PLC and enhancers of paracellular permeability fit well into this correlation. Therefore, phosphocholines are likely to increase paracellular permeability by modulating the signal transduction pathway initiated by a PLC-catalyzed reaction rather than by physically altering the cell membrane.
• Monoacylglycerols as transmembrane Cl− anion transporters
  作者：Soheila Bahmanjah、Ning Zhang、Jeffery T. Davis

  DOI：10.1039/c2cc18148g

  日期：——

  We report that the amphiphilic natural product, monoacylglycerol 1, functions as a transmembrane Cl(-)/NO(3)(-) anion transporter. The 1,2-diol group is crucial for the transport function since diacylglycerol and triacylglycerol analogs are not anion transporters. Furthermore, adding another hydrogen bond donor to the glycerol head-group and perfluorination of the acyl tail gave synthetic analogs with

  我们报告说两亲的天然产物，单酰基甘油1，作为跨膜Cl（-）/ NO（3）（-）阴离子转运蛋白。1，2-二醇基对于转运功能至关重要，因为二酰基甘油和三酰基甘油类似物不是阴离子转运蛋白。此外，将另一个氢键供体添加到甘油的头基和酰基尾的全氟化得到具有改进的Cl（-）膜运输性质的合成类似物。