(7Z,10Z,25Z)-(5S,20S)-15,30-dioxo-5,20-dipropyl-1,16-dioxa-4,19-diazacyclotriaconta-7,10,25-triene-4,19-dicarboxylic acid di-tert-butyl ester | 329184-86-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: (7Z,10Z,25Z)-(5S,20S)-15,30-dioxo-5,20-dipropyl-1,16-dioxa-4,19-diazacyclotriaconta-7,10,25-triene-4,19-dicarboxylic acid di-tert-butyl ester
• 英文别名: ditert-butyl (5S,10Z,20S,22Z,25Z)-15,30-dioxo-5,20-dipropyl-1,16-dioxa-4,19-diazacyclotriaconta-10,22,25-triene-4,19-dicarboxylate
• CAS: 329184-86-3
• 化学式: C₄₂H₇₂N₂O₈
• 分子量: 733.042
• InChiKey: WYPKKLQJIFMQQQ-HOWIDSJISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.9
• 重原子数：
  52
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  112
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (7Z,10Z,25Z)-(5S,20S)-15,30-dioxo-5,20-dipropyl-1,16-dioxa-4,19-diazacyclotriaconta-7,10,25-triene-4,19-dicarboxylic acid di-tert-butyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 以89%的产率得到(7Z,10Z,25Z)-(5S,20S)-5,20-dipropyl-1,16-dioxa-4,19-diazacyclotriaconta-7,10,25-triene-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：

  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 、 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 121.0h， 生成 (7Z,10Z,25Z)-(5S,20S)-15,30-dioxo-5,20-dipropyl-1,16-dioxa-4,19-diazacyclotriaconta-7,10,25-triene-4,19-dicarboxylic acid di-tert-butyl ester
  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.