methyl (Z)-3-pentyl-2-decen-4-ynoate | 475630-69-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl (Z)-3-pentyl-2-decen-4-ynoate
• 英文别名: methyl (Z)-3-pentyldec-2-en-4-ynoate
• CAS: 475630-69-4
• 化学式: C₁₆H₂₆O₂
• 分子量: 250.381
• InChiKey: PNVOOLKCMFVREE-PFONDFGASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  18
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl (Z)-3-pentyl-2-decen-4-ynoate 在 copper(l) iodide 、 二(氰基苯)二氯化钯 、 三苯胂 、 碘 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 145.0h， 生成 4,6-dipentyl-5-phenyl-2(2H)-pyranone
  参考文献：
  名称：

  New procedures for the selective synthesis of 2(2H)-pyranone derivatives and 3-aryl-4-iodoisocoumarins

  摘要：

  5-Iodo-2(2H)-pyranone derivatives have been selectively synthesized by reaction of stereodefined methyl 2-en-4-ynoates with iodine in MeCN, CH2Cl2 or C6H6 at 20degreesC (Method C) or by treatment of these esters with ICl in CH2Cl2 at 20degreesC (Method B). Methods B and C proved also to be suitable for the preparation of 3-aryl-4-iodoisocoumarins from the corresponding methyl 2-(arylethynyl)benzoates. Interestingly, the high selectivity of iodolactonization of stereodefined methyl 2-en-4-ynoates by Method B allowed preparation in moderate yields of 2(2H)-pyranone derivatives by a one-pot sequence of iodolactonization and Stille-type reactions. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00469-6
• 作为产物：
  描述：

  1-庚炔 、 methyl (Z)-3-iodo-2-octenoate 在 copper(l) iodide 、 四(三苯基膦)钯 、 三乙胺 作用下， 以 苯 为溶剂， 反应 19.0h， 以94%的产率得到methyl (Z)-3-pentyl-2-decen-4-ynoate
  参考文献：
  名称：

  New procedures for the selective synthesis of 2(2H)-pyranone derivatives and 3-aryl-4-iodoisocoumarins

  摘要：

  5-Iodo-2(2H)-pyranone derivatives have been selectively synthesized by reaction of stereodefined methyl 2-en-4-ynoates with iodine in MeCN, CH2Cl2 or C6H6 at 20degreesC (Method C) or by treatment of these esters with ICl in CH2Cl2 at 20degreesC (Method B). Methods B and C proved also to be suitable for the preparation of 3-aryl-4-iodoisocoumarins from the corresponding methyl 2-(arylethynyl)benzoates. Interestingly, the high selectivity of iodolactonization of stereodefined methyl 2-en-4-ynoates by Method B allowed preparation in moderate yields of 2(2H)-pyranone derivatives by a one-pot sequence of iodolactonization and Stille-type reactions. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00469-6

文献信息

• New procedures for the selective synthesis of 2(2H)-pyranone derivatives and 3-aryl-4-iodoisocoumarins
  作者：Matteo Biagetti、Fabio Bellina、Adriano Carpita、Paolo Stabile、Renzo Rossi

  DOI：10.1016/s0040-4020(02)00469-6

  日期：2002.6

  5-Iodo-2(2H)-pyranone derivatives have been selectively synthesized by reaction of stereodefined methyl 2-en-4-ynoates with iodine in MeCN, CH2Cl2 or C6H6 at 20degreesC (Method C) or by treatment of these esters with ICl in CH2Cl2 at 20degreesC (Method B). Methods B and C proved also to be suitable for the preparation of 3-aryl-4-iodoisocoumarins from the corresponding methyl 2-(arylethynyl)benzoates. Interestingly, the high selectivity of iodolactonization of stereodefined methyl 2-en-4-ynoates by Method B allowed preparation in moderate yields of 2(2H)-pyranone derivatives by a one-pot sequence of iodolactonization and Stille-type reactions. (C) 2002 Elsevier Science Ltd. All rights reserved.