[2-(tert-butyldiphenylsilanyloxy)ethyl]-[(S)-(3Z,6Z)-10-(4-methyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl)-1-propyldeca-3,6-dienyl]carbamic acid dimethylethyl ester | 329184-69-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [2-(tert-butyldiphenylsilanyloxy)ethyl]-[(S)-(3Z,6Z)-10-(4-methyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl)-1-propyldeca-3,6-dienyl]carbamic acid dimethylethyl ester
• 英文别名: tert-butyl N-[2-[tert-butyl(diphenyl)silyl]oxyethyl]-N-[(4S,6Z,9Z)-13-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)trideca-6,9-dien-4-yl]carbamate
• CAS: 329184-69-2
• 化学式: C₄₂H₆₃NO₆Si
• 分子量: 706.051
• InChiKey: LJJIGNVHPISRDB-ILTKUKSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.77
• 重原子数：
  50
• 可旋转键数：
  20
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  66.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [2-(tert-butyldiphenylsilanyloxy)ethyl]-[(S)-(3Z,6Z)-10-(4-methyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl)-1-propyldeca-3,6-dienyl]carbamic acid dimethylethyl ester 在 palladium diacetate 吗啉 、 4-二甲氨基吡啶 、 lithium hydroxide 、 sodium hydrogen sulfate 、 四丁基氟化铵 、 N,N'-二环己基碳二亚胺 、 三苯基膦 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 二氯甲烷 、 水 为溶剂， 反应 39.5h， 生成 (S)-(5Z,8Z)-11-[[2-(tert-butyldiphenylsilanyloxy)ethyl](dimethylethoxycarbonyl)amino]tetradeca-5,8-dienoic acid 2-[tert-butoxycarbonyl-((S)-(Z)-10-carboxy-1-propyldec-6-enyl)amino]ethyl 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
• 作为产物：
  描述：

  4-methyl-N-[(S)-1-propyl-5-(tetrahydropyran-2-yloxy)pent-3-ynyl]benzenesulfonamide 在 Lindlar's catalyst copper(l) iodide 、 正丁基锂 、 萘 、 氢气 、 溴 、 sodium 、 sodium hydride 、 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 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 97.0h， 生成 [2-(tert-butyldiphenylsilanyloxy)ethyl]-[(S)-(3Z,6Z)-10-(4-methyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl)-1-propyldeca-3,6-dienyl]carbamic acid dimethylethyl 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.