(Z)-(5S,11R)-11-isopropenyl-3-methyl-7-oxo-6,16-dioxatricyclo[11.2.1.1(5,8)]heptadeca-1(15),2,8(17),13-tetraene-14-carbaldehyde | 1224868-52-3

• 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: (Z)-(5S,11R)-11-isopropenyl-3-methyl-7-oxo-6,16-dioxatricyclo[11.2.1.1(5,8)]heptadeca-1(15),2,8(17),13-tetraene-14-carbaldehyde
• 英文别名: (2Z,5S,11R)-3-methyl-7-oxo-11-prop-1-en-2-yl-6,16-dioxatricyclo[11.2.1.15,8]heptadeca-1(15),2,8(17),13-tetraene-14-carbaldehyde
• CAS: 1224868-52-3
• 化学式: C₂₀H₂₂O₄
• 分子量: 326.392
• InChiKey: POJUTQNXIAHCCG-OAOOFNTCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  甲醇 、 (Z)-(5S,11R)-11-isopropenyl-3-methyl-7-oxo-6,16-dioxatricyclo[11.2.1.1(5,8)]heptadeca-1(15),2,8(17),13-tetraene-14-carbaldehyde 在 sodium cyanide 、 溶剂黄146 、 manganese(IV) oxide 作用下， 以 甲醇 为溶剂， 反应 22.0h， 以65%的产率得到(Z)-deoxypukalide
  参考文献：
  名称：

  Total synthesis of (+)-Z-deoxypukalide, a furanobutenolide-based cembranoid isolated from the pacific octocoral Leptogorgia spp.

  摘要：

  A total synthesis of (+)-Z-deoxypukalide 3 using a combination of Stille and Nozaki-Hiyama-Kishi(NHK) coupling reactions as key steps, is described. During this study a new practical synthesis of the substituted butenolide intermediate 10, based on a combination of RCM and CM reactions from the cyclobutene ester 21 in the presence of 2-methylpropenol was also developed. Attempts to apply the intramolecular NHK reaction to the substrates 8a and 8b containing an ester group adjacent to the reacting aldehyde functionality gave disappointing low yields (<6%) of the corresponding coupled products 9. The synthetic (+)-Z-deoxypukalide 3 was correlated with naturally derived material, and also with pukalide 1, the first member of the furanobutenolide-based cembranoids to be isolated from corals. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.01.059
• 作为产物：
  描述：

  (Z)-(5S,11R)-14-hydroxymethyl-11-isopropenyl-3-methyl-6,16-dioxa-tricyclo[11.2.1.1(5,8)]heptadeca-1(15),2,8(17),13-tetraen-7-one 在 manganese(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以97%的产率得到(Z)-(5S,11R)-11-isopropenyl-3-methyl-7-oxo-6,16-dioxatricyclo[11.2.1.1(5,8)]heptadeca-1(15),2,8(17),13-tetraene-14-carbaldehyde
  参考文献：
  名称：

  Total synthesis of (+)-Z-deoxypukalide, a furanobutenolide-based cembranoid isolated from the pacific octocoral Leptogorgia spp.

  摘要：

  A total synthesis of (+)-Z-deoxypukalide 3 using a combination of Stille and Nozaki-Hiyama-Kishi(NHK) coupling reactions as key steps, is described. During this study a new practical synthesis of the substituted butenolide intermediate 10, based on a combination of RCM and CM reactions from the cyclobutene ester 21 in the presence of 2-methylpropenol was also developed. Attempts to apply the intramolecular NHK reaction to the substrates 8a and 8b containing an ester group adjacent to the reacting aldehyde functionality gave disappointing low yields (<6%) of the corresponding coupled products 9. The synthetic (+)-Z-deoxypukalide 3 was correlated with naturally derived material, and also with pukalide 1, the first member of the furanobutenolide-based cembranoids to be isolated from corals. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.01.059

文献信息

• Total synthesis of (+)-Z-deoxypukalide, a furanobutenolide-based cembranoid isolated from the pacific octocoral Leptogorgia spp.
  作者：Bencan Tang、Christopher D. Bray、Gerald Pattenden、Joseph Rogers

  DOI：10.1016/j.tet.2010.01.059

  日期：2010.3

  A total synthesis of (+)-Z-deoxypukalide 3 using a combination of Stille and Nozaki-Hiyama-Kishi(NHK) coupling reactions as key steps, is described. During this study a new practical synthesis of the substituted butenolide intermediate 10, based on a combination of RCM and CM reactions from the cyclobutene ester 21 in the presence of 2-methylpropenol was also developed. Attempts to apply the intramolecular NHK reaction to the substrates 8a and 8b containing an ester group adjacent to the reacting aldehyde functionality gave disappointing low yields (<6%) of the corresponding coupled products 9. The synthetic (+)-Z-deoxypukalide 3 was correlated with naturally derived material, and also with pukalide 1, the first member of the furanobutenolide-based cembranoids to be isolated from corals. (C) 2010 Elsevier Ltd. All rights reserved.