(3-acetoxypropyl)triphenylphosphonium bromide | 30698-17-0

• 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: (3-acetoxypropyl)triphenylphosphonium bromide
• 英文别名: [3-(Acetyloxy)propyl](triphenyl)phosphanium bromide；3-acetyloxypropyl(triphenyl)phosphanium;bromide
• CAS: 30698-17-0
• 化学式: Br*C₂₃H₂₄O₂P
• 分子量: 443.32
• InChiKey: CKHKCGZZNGLAKC-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.94
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3-acetoxypropyl)triphenylphosphonium bromide 在 palladium on activated charcoal 二环己烷并-18-冠醚-6 、 硫酸 、 potassium tert-butylate 、 氢气 、 碘 、 甲基磺酰氯 、 potassium iodide 、 sodium nitrite 作用下， 以 乙醇 、 二氯甲烷 、 溶剂黄146 为溶剂， -7.0~25.0 ℃ 、275.79 kPa 条件下， 反应 2.67h， 生成 3'-(4-acetoxybutyl)-3,5-diiodo-O-methyl-N-(triflioroacetyl)-L-thyronine ethyl ester
  参考文献：
  名称：

  Thyroid hormone analogs. Synthesis of 3'-substituted 3,5-diiodo-L-thyronines and quantitative structure-activity studies of in vitro and in vivo thyromimetic activities in rat liver and heart

  摘要：

  Twenty-nine novel 3'-substituted derivatives of the thyroid hormone 3,3',5-triiodo-L-thyronine (T3) have been synthesized by using established methods and by a new route involving manipulation of a 3'-formyl intermediate. In vitro hormone receptor binding (to intact nuclei) and in vivo thyromimetic activity (induction of mitochondrial 3-phosphoglycerate oxidoreductase, GPDH) were measured in rat liver and heart for these new analogues and for the 18 previously reported 3'-substituted 3,5-diiodo-L-thyronines. Analysis of the binding data using theoretical conformational and quantitative structure-affinity methods implies that the 3'-substituent recognition site on the thyroid hormone receptor is hydrophobic and limited in depth to the length of the natural iodo substituent, but has sufficient width to accommodate a phenyl or cyclohexyl group. Receptor binding is reduced by approximately 10-fold in 3'-acyl derivatives which form strong intramolecular acceptor hydrogen bonds with the adjacent 4'-hydroxyl. The compounds studied showed no differences in their relative affinities for heart and liver nuclei, suggesting that receptors in these tissues are similar. However, the relationships between thyromimetic activity (induction of GPDH) and nuclear binding showed some tissue differences. A high correlation between activity and binding is observed for full agonists in the heart, but an equally significant correlation for the liver data is only seen when 3'-substituent bulk (molar refractivity) is included in the analysis. These results suggest the possibility that differential tissue penetration or access to receptors may occur in vivo.

  DOI：

  10.1021/jm00396a008
• 作为产物：
  描述：

  丁基氨基甲酸酯 、 三苯基膦 以 苯 为溶剂， 以218.0g的产率得到(3-acetoxypropyl)triphenylphosphonium bromide
  参考文献：
  名称：

  (6Z,9Z)-3,4-环氧十九碳二烯的制备方法

  摘要：

  本发明提供一种(6Z,9Z)‑3,4‑环氧十九碳二烯的制备方法，利用Z3‑13:Ald、[Ph+3pC2H5CH=CH C2H5]Br‑‑、K2CO3、冠醚和苯制得所述(3Z,3Z,9Z)‑十九碳三烯，利用所述(3Z,3Z,9Z)‑十九碳三烯与间氯过氧苯甲酸在冰乙酸中制得(6Z,9Z)‑3,4‑环氧十九碳二烯。和传统方法相比，本发明通过两次相转移Wittig反应构建碳碳双键来延伸碳链，避免了炔化物路线所需的严格无水环境、避免了传统Wittig中烃基锂遇水易燃易爆及反应所需的低温条件（＜‑20℃），所用反应条件温和、易操作；制备中所需原料均为便宜易得的常用化学试剂，不含异构体杂质，所得产物容易纯化；反应总得率比传统方法提高20%以上。

  公开号：

  CN115466232A

文献信息

• (6Z,9Z)-3,4-环氧十九碳二烯的制备方法
  申请人：山西农业大学

  公开号：CN115466232A

  公开（公告）日：2022-12-13

  本发明提供一种(6Z,9Z)‑3,4‑环氧十九碳二烯的制备方法，利用Z3‑13:Ald、[Ph+3pC2H5CH=CH C2H5]Br‑‑、K2CO3、冠醚和苯制得所述(3Z,3Z,9Z)‑十九碳三烯，利用所述(3Z,3Z,9Z)‑十九碳三烯与间氯过氧苯甲酸在冰乙酸中制得(6Z,9Z)‑3,4‑环氧十九碳二烯。和传统方法相比，本发明通过两次相转移Wittig反应构建碳碳双键来延伸碳链，避免了炔化物路线所需的严格无水环境、避免了传统Wittig中烃基锂遇水易燃易爆及反应所需的低温条件（＜‑20℃），所用反应条件温和、易操作；制备中所需原料均为便宜易得的常用化学试剂，不含异构体杂质，所得产物容易纯化；反应总得率比传统方法提高20%以上。
• Thyroid hormone analogs. Synthesis of 3'-substituted 3,5-diiodo-L-thyronines and quantitative structure-activity studies of in vitro and in vivo thyromimetic activities in rat liver and heart
  作者：Paul D. Leeson、David Ellis、John C. Emmett、Virendra P. Shah、Graham A. Showell、Anthony H. Underwood

  DOI：10.1021/jm00396a008

  日期：1988.1

  Twenty-nine novel 3'-substituted derivatives of the thyroid hormone 3,3',5-triiodo-L-thyronine (T3) have been synthesized by using established methods and by a new route involving manipulation of a 3'-formyl intermediate. In vitro hormone receptor binding (to intact nuclei) and in vivo thyromimetic activity (induction of mitochondrial 3-phosphoglycerate oxidoreductase, GPDH) were measured in rat liver and heart for these new analogues and for the 18 previously reported 3'-substituted 3,5-diiodo-L-thyronines. Analysis of the binding data using theoretical conformational and quantitative structure-affinity methods implies that the 3'-substituent recognition site on the thyroid hormone receptor is hydrophobic and limited in depth to the length of the natural iodo substituent, but has sufficient width to accommodate a phenyl or cyclohexyl group. Receptor binding is reduced by approximately 10-fold in 3'-acyl derivatives which form strong intramolecular acceptor hydrogen bonds with the adjacent 4'-hydroxyl. The compounds studied showed no differences in their relative affinities for heart and liver nuclei, suggesting that receptors in these tissues are similar. However, the relationships between thyromimetic activity (induction of GPDH) and nuclear binding showed some tissue differences. A high correlation between activity and binding is observed for full agonists in the heart, but an equally significant correlation for the liver data is only seen when 3'-substituent bulk (molar refractivity) is included in the analysis. These results suggest the possibility that differential tissue penetration or access to receptors may occur in vivo.
• Bestmann, Hans Juergen; Roth, Kurt; Michaelis, Karl, Liebigs Annalen der Chemie, 1987, p. 417 - 422
  作者：Bestmann, Hans Juergen、Roth, Kurt、Michaelis, Karl、Vostrowsky, Otto、Schaefer, Hans J.、Michaelis, Ralf

  DOI：——

  日期：——