(3S,9R,10S)-9-methyl-10-((tetrahydropyran-2'-yl)oxy)undec-1-en-3-yl acrylate | 1059187-51-7

• 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: (3S,9R,10S)-9-methyl-10-((tetrahydropyran-2'-yl)oxy)undec-1-en-3-yl acrylate
• 英文别名: [(3S,9R,10S)-9-methyl-10-(oxan-2-yloxy)undec-1-en-3-yl] prop-2-enoate
• CAS: 1059187-51-7
• 化学式: C₂₀H₃₄O₄
• 分子量: 338.488
• InChiKey: HEURWAQHHATUNR-RYRLBTNJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  24
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S,9R,10S)-9-methyl-10-((tetrahydropyran-2'-yl)oxy)undec-1-en-3-yl acrylate 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以91%的产率得到(2S)-2-[(6R,7S)-6-methyl-7-(oxan-2-yloxy)octyl]-2H-furan-5-one
  参考文献：
  名称：

  Total synthesis of (4S,10R)-4-hydroxy-10-methyl-11-oxododec-2-en-1,4-olide and related bioactive marine butenolides

  摘要：

  Marine-derived microorganisms produce structurally diverse butenolides possessing a variety of bioactivities. Described here is the total synthesis of (4S, 10R)-4-hydroxy-10-nnethyl-11-oxododec-2-en-1,4-olide and a related butenolide containing anti stereochemistry at C10-C11. A three-module coupling strategy has been established for synthesis of the stereoisomers of the naturally Occurring butenolides by assembling the C3-C7 and C9-C12 fragments via double alkylation of a 1,3-dithiane. The C10-C11 stereochemistry could be easily controlled by an asymmetric aldol condensation, while the butenolide unit was efficiently constructed according to the ring-closing metathesis protocol. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.06.028
• 作为产物：
  描述：

  、 丙烯酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以81%的产率得到(3S,9R,10S)-9-methyl-10-((tetrahydropyran-2'-yl)oxy)undec-1-en-3-yl acrylate
  参考文献：
  名称：

  Total synthesis of (4S,10R)-4-hydroxy-10-methyl-11-oxododec-2-en-1,4-olide and related bioactive marine butenolides

  摘要：

  Marine-derived microorganisms produce structurally diverse butenolides possessing a variety of bioactivities. Described here is the total synthesis of (4S, 10R)-4-hydroxy-10-nnethyl-11-oxododec-2-en-1,4-olide and a related butenolide containing anti stereochemistry at C10-C11. A three-module coupling strategy has been established for synthesis of the stereoisomers of the naturally Occurring butenolides by assembling the C3-C7 and C9-C12 fragments via double alkylation of a 1,3-dithiane. The C10-C11 stereochemistry could be easily controlled by an asymmetric aldol condensation, while the butenolide unit was efficiently constructed according to the ring-closing metathesis protocol. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.06.028

文献信息

• Total synthesis of (4S,10R)-4-hydroxy-10-methyl-11-oxododec-2-en-1,4-olide and related bioactive marine butenolides
  作者：Wei-Min Dai、Lei Shi、Yannian Li

  DOI：10.1016/j.tetasy.2008.06.028

  日期：2008.7

  Marine-derived microorganisms produce structurally diverse butenolides possessing a variety of bioactivities. Described here is the total synthesis of (4S, 10R)-4-hydroxy-10-nnethyl-11-oxododec-2-en-1,4-olide and a related butenolide containing anti stereochemistry at C10-C11. A three-module coupling strategy has been established for synthesis of the stereoisomers of the naturally Occurring butenolides by assembling the C3-C7 and C9-C12 fragments via double alkylation of a 1,3-dithiane. The C10-C11 stereochemistry could be easily controlled by an asymmetric aldol condensation, while the butenolide unit was efficiently constructed according to the ring-closing metathesis protocol. (C) 2008 Elsevier Ltd. All rights reserved.