4-(hexadecyloxy)-3-(phenylmethoxy)-1-butanol | 113485-73-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(hexadecyloxy)-3-(phenylmethoxy)-1-butanol
• 英文别名: 4-hexadecoxy-3-phenylmethoxybutan-1-ol
• CAS: 113485-73-7
• 化学式: C₂₇H₄₈O₃
• 分子量: 420.676
• InChiKey: PERCPBOKXGFQMZ-UHFFFAOYSA-N

物化性质

• 沸点：
  530.8±40.0 °C(Predicted)
• 密度：
  0.942±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  30
• 可旋转键数：
  22
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(hexadecyloxy)-3-(phenylmethoxy)-1-butanol 在 palladium on activated charcoal 氢气 、 sodium acetate 、 三乙胺 作用下， 以 甲醇 、 氯仿 、 溶剂黄146 为溶剂， 反应 21.0h， 生成 8-(acetyloxy)-4-hydroxy-N,N,N-trimethyl-3,5,10-trioxa-4-phosphahexacosan-1-aminium 4-oxide, hydroxide
  参考文献：
  名称：

  Analogs of platelet activating factor (PAF). 2. Some modifications of the glycerine backbone

  摘要：

  Racemic analogues of platelet activating factor (PAF) that contain a methylene group between the C2 and C3 carbon atoms (39) or between the C1 and C2 carbon atoms (40) have been synthesized. These compounds show reduced platelet aggregation and hypotensive activity as measured against racemic C16 PAF. Compounds in which the C1 carbon atom of PAF is substituted with one or two methyl groups (41 and 42, respectively) or the C3 carbon is substituted with a single methyl group (43) have been synthesized. Platelet aggregation and hypotensive responses produced by these compounds are significantly less than those obtained with racemic C16 PAF. None of the above compounds exhibit a separation of the platelet aggregation and hypotensive activities.

  DOI：

  10.1021/jm00147a010
• 作为产物：
  描述：

  1-十六烷醇 在 sodium hydroxide 、 硼烷四氢呋喃络合物 、 草酰氯 、 硼烷 、 双氧水 、 sodium hydride 、 magnesium 、 二甲基亚砜 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 46.83h， 生成 4-(hexadecyloxy)-3-(phenylmethoxy)-1-butanol
  参考文献：
  名称：

  Analogs of platelet activating factor (PAF). 2. Some modifications of the glycerine backbone

  摘要：

  Racemic analogues of platelet activating factor (PAF) that contain a methylene group between the C2 and C3 carbon atoms (39) or between the C1 and C2 carbon atoms (40) have been synthesized. These compounds show reduced platelet aggregation and hypotensive activity as measured against racemic C16 PAF. Compounds in which the C1 carbon atom of PAF is substituted with one or two methyl groups (41 and 42, respectively) or the C3 carbon is substituted with a single methyl group (43) have been synthesized. Platelet aggregation and hypotensive responses produced by these compounds are significantly less than those obtained with racemic C16 PAF. None of the above compounds exhibit a separation of the platelet aggregation and hypotensive activities.

  DOI：

  10.1021/jm00147a010

文献信息

• SYNTHESIS AND BIOLOGICAL ACTIVITIES OF BIOISOSTERIC O-CARBA-ANALOGUES OF PLATELET ACTIVATING FACTOR (PAF)
  作者：Norio Nakamura、Hideki Miyazaki、Nobuyuki Ohkawa、Hiroyuki Koike、Toshio Sada、Fumitoshi Asai、Shinsaku Kobayashi

  DOI：10.1248/cpb.32.2452

  日期：——

  Four types of O-carba-analogues of C16-PAF were synthesized : d1-2-acetoxyeicosylphosphoryl choline (1), dl-3-hexadecyloxy-2-(2-oxopropyl) propylphosphoryl choline (2), d1-and (S)-(-)-3-acetoxy-4-hexa-decyloxybutylphosphonyl choline (3), and d1-2-acetoxy-3-hexadecyloxypropyl (3-trimethylammonio) propylphosphonate (4). Both in hypotension and in platelet aggregation, (S)-(-)-3 was one third as potent as synthetic C16-PAF, whereas 1, 2 and 4 were 100-3, 000 times less potent.

  合成了四种C16-PAF的O-carb-类似物：d1-2-乙酰氧基二十碳酰基磷脂酰胆碱（1）、dl-3-十六烷氧基-2-(2-氧丙基)丙基磷脂酰胆碱（2）、d1-和(S)-(-)-3-乙酰氧基-4-十六烷氧基丁基磷酸胆碱（3）以及d1-2-乙酰氧基-3-十六烷氧基丙基(3-三甲基铵)丙基磷酸酯（4）。在低血压和血小板聚集的实验中，(S)-(-)-3的效力为合成C16-PAF的三分之一，而1、2和4的效力则低于100-3000倍。
• Antihypertensive phosphate derivatives
  申请人：American Cyanamid Company

  公开号：US04699990A1

  公开（公告）日：1987-10-13

  Antihypertensive phosphate derivatives are described having the following formula: ##STR1## wherein n is an integer 1 or 2; m is an integer 1 or 2, and the sum of n and m must be 3; X is selected from the group consisting of C.sub.1 -C.sub.24 branched or straight chain alkoxy and substituted phenoxy wherein the substituents are selected from one or more of the group consisting of C.sub.1 -C.sub.20 branched or straight chain alkyl, C.sub.1 -C.sub.20 branched or straight chain alkoxy, halogen, phenyl and substituted phenyl; T is selected from the group consisting of hydrogen and ##STR2## wherein R.sub.1 is selected from the group consisting of hydrogen, C.sub.1 -C.sub.4 branched or straight chain alkyl, C.sub.1 -C.sub.4 branched or straight chain alkoxy and C.sub.1 -C.sub.4 branched or straight chain alkylamino, Q is a bivalent radical selected from the group consisting of --(CH.sub.2).sub.p -- and --(CHR).sub.p --, where p is an integer from 2 to 12 and the moiety --(CHR).sub.p -- represents an alkylene chain which is substituted by one or more C.sub.1 -C.sub.10 alkyl groups or phenyl groups; Z is selected from the group consisting of --.sup.+ N(R.sub.2).sub.3 and ##STR3## wherein R.sub.2 may be the same or different and is selected from the group consisting of hydrogen and C.sub.1 -C.sub.4 branched or straight chain alkyl and q is an integer from 4 to 7.

  描述具有以下公式的降压磷酸盐衍生物：##STR1##其中n是整数1或2；m是整数1或2，n和m的总和必须为3；X从羧基或取代苯氧基组成的群中选择，其中取代基选择自羧基或取代苯基组成的群中的一个或多个，这些群包括碳链长度为C.sub.1-C.sub.20的支链或直链烷氧基、碳链长度为C.sub.1-C.sub.20的支链或直链烷基、卤素、苯基和取代苯基；T从氢和##STR2##中选择，其中R.sub.1从氢、碳链长度为C.sub.1-C.sub.4的支链或直链烷基、碳链长度为C.sub.1-C.sub.4的支链或直链烷氧基和碳链长度为C.sub.1-C.sub.4的支链或直链烷基氨基组成的群中选择，Q是选择自--(CH.sub.2).sub.p --和--(CHR).sub.p --的二价基团，其中p是2到12之间的整数，而基团--(CHR).sub.p --表示一个被一个或多个碳链长度为C.sub.1-C.sub.10的烷基或苯基取代的烷基链；Z从--.sup.+ N(R.sub.2).sub.3和##STR3##中选择，其中R.sub.2可以相同也可以不同，选择自氢和碳链长度为C.sub.1-C.sub.4的支链或直链烷基，q是4到7之间的整数。
• US4699990A
  申请人：——

  公开号：US4699990A

  公开（公告）日：1987-10-13
• US4900731A
  申请人：——

  公开号：US4900731A

  公开（公告）日：1990-02-13
• Analogs of platelet activating factor (PAF). 2. Some modifications of the glycerine backbone
  作者：A. Wissner、R. E. Schaub、P. E. Sum、C. A. Kohler、B. M. Goldstein

  DOI：10.1021/jm00147a010

  日期：1985.9

  Racemic analogues of platelet activating factor (PAF) that contain a methylene group between the C2 and C3 carbon atoms (39) or between the C1 and C2 carbon atoms (40) have been synthesized. These compounds show reduced platelet aggregation and hypotensive activity as measured against racemic C16 PAF. Compounds in which the C1 carbon atom of PAF is substituted with one or two methyl groups (41 and 42, respectively) or the C3 carbon is substituted with a single methyl group (43) have been synthesized. Platelet aggregation and hypotensive responses produced by these compounds are significantly less than those obtained with racemic C16 PAF. None of the above compounds exhibit a separation of the platelet aggregation and hypotensive activities.