4-methyl-N-[(S)-1-propyl-5-(tetrahydropyran-2-yloxy)pent-3-ynyl]benzenesulfonamide | 329184-63-6

• 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-methyl-N-[(S)-1-propyl-5-(tetrahydropyran-2-yloxy)pent-3-ynyl]benzenesulfonamide
• 英文别名: 4-methyl-N-[(4S)-8-(oxan-2-yloxy)oct-6-yn-4-yl]benzenesulfonamide
• CAS: 329184-63-6
• 化学式: C₂₀H₂₉NO₄S
• 分子量: 379.521
• InChiKey: SNRXEXJDHWQNJH-LROBGIAVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  73
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-methyl-N-[(S)-1-propyl-5-(tetrahydropyran-2-yloxy)pent-3-ynyl]benzenesulfonamide 在 palladium diacetate 、 Lindlar's catalyst 吗啉 、 4-二甲氨基吡啶 、 lithium hydroxide 、 sodium hydrogen sulfate 、 copper(l) iodide 、 正丁基锂 、 萘 、 四丁基氟化铵 、 2-氯-1-甲基吡啶碘化物 、 氢气 、 溴 、 sodium 、 sodium hydride 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 三苯基膦 、 三氟乙酸 、 1,2-双(二苯基膦)乙烷 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 乙醇 、 正己烷 、 二氯甲烷 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 141.75h， 生成 (10Z,25Z)-(5S,20S)-5,20-dipropyl-1,16-dioxa-4,19-diazacyclotriaconta-10,25-diene-15,30-dione
  参考文献：
  名称：

  Synthesis of Unsaturated Polyazamacrolides from the Ladybird Beetle Subcoccinella vigintiquatuorpunctata

  摘要：

  The pupal defensive secretion of the ladybird beetle Subcoccinella vigintiquatuorpunctata consists of a mixture of macrocyclic polyamines (polyazamacrolides, PAMLs) dominated by three dimeric, 30-membered bislactones (1, 2, and 3), which represent the three possible head-to-tail combinations of the two building blocks (S)-(Z)-11-(2-hydroxyethylamino)-5-tetradecenoic acid (4) and (S)-(5Z,8Z)-11-(2-hydroxyethylamino)-5,8-tetradecadienoic acid (5). We now report the synthesis of these three alkaloids via a route involving the nucleophilic opening of a chiral aziridine as a common step.

  DOI：

  10.1021/jo001200w
• 作为产物：
  描述：

  哌喃 、 (2S)-2-propyl-1-(p-tolylsulfonyl)aziridine 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 24.0h， 以88%的产率得到4-methyl-N-[(S)-1-propyl-5-(tetrahydropyran-2-yloxy)pent-3-ynyl]benzenesulfonamide
  参考文献：
  名称：

  Synthesis of Unsaturated Polyazamacrolides from the Ladybird Beetle Subcoccinella vigintiquatuorpunctata

  摘要：

  The pupal defensive secretion of the ladybird beetle Subcoccinella vigintiquatuorpunctata consists of a mixture of macrocyclic polyamines (polyazamacrolides, PAMLs) dominated by three dimeric, 30-membered bislactones (1, 2, and 3), which represent the three possible head-to-tail combinations of the two building blocks (S)-(Z)-11-(2-hydroxyethylamino)-5-tetradecenoic acid (4) and (S)-(5Z,8Z)-11-(2-hydroxyethylamino)-5,8-tetradecadienoic acid (5). We now report the synthesis of these three alkaloids via a route involving the nucleophilic opening of a chiral aziridine as a common step.

  DOI：

  10.1021/jo001200w

文献信息

• Synthesis of Unsaturated Polyazamacrolides from the Ladybird Beetle <i>Subcoccinella </i><i>v</i><i>igintiquatuorpunctata</i>
  作者：Matthew R. Gronquist、Jerrold Meinwald

  DOI：10.1021/jo001200w

  日期：2001.2.1

  The pupal defensive secretion of the ladybird beetle Subcoccinella vigintiquatuorpunctata consists of a mixture of macrocyclic polyamines (polyazamacrolides, PAMLs) dominated by three dimeric, 30-membered bislactones (1, 2, and 3), which represent the three possible head-to-tail combinations of the two building blocks (S)-(Z)-11-(2-hydroxyethylamino)-5-tetradecenoic acid (4) and (S)-(5Z,8Z)-11-(2-hydroxyethylamino)-5,8-tetradecadienoic acid (5). We now report the synthesis of these three alkaloids via a route involving the nucleophilic opening of a chiral aziridine as a common step.