methyl 8-(2-furanyl)-8-hydroxy-4(Z)-octenoate | 132803-40-8

• 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 8-(2-furanyl)-8-hydroxy-4(Z)-octenoate
• 英文别名: methyl (Z)-8-(furan-2-yl)-8-hydroxyoct-4-enoate
• CAS: 132803-40-8
• 化学式: C₁₃H₁₈O₄
• 分子量: 238.284
• InChiKey: DCEPKARNFRLEAZ-IHWYPQMZSA-N

物化性质

• 沸点：
  330.7±42.0 °C(Predicted)
• 密度：
  1.103±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  59.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 8-(2-furanyl)-8-hydroxy-4(Z)-octenoate 在 水 、 zinc(II) chloride 作用下， 以 1,4-二氧六环 为溶剂， 反应 22.0h， 生成 (Z)-7-((1S,2R)-2-hydroxy-5-oxocyclopent-3-en-1-yl)hept-4-enoic acid
  参考文献：
  名称：

  An efficient synthesis of the antisecretory prostaglandin enisoprost

  摘要：

  A 13-step synthesis of the antisecretory prostaglandin enisoprost was previously reported by Collins et al. 1 in 1983. The reported synthesis involved coupling of enone 6 with a cuprate reagent2 derived from a suitably substituted vinylstannane and cuprous pentyne to give enisoprost 10 in 60% yield after removal of protecting groups and chromatographic purification.Further development work on the synthesis of enisoprost has resulted in an improved method for preparing the key enone precursor 6 as outlined in Scheme I. Use of the trans-vinyl iodide 9 in place of the corresponding vinylstannane derivative and use of dilithiocyanocuprate3 coupling technology resulted in an 85% isolated yield of enisoprost 10 as outlined in Scheme II.Direct conversion of the terminal acetylene 8b into protected enisoprost via a one-pot process has also been accomplished as outlined in Scheme II. This latter modification greatly simplified the process and resulted in a 71% isolated yield of enisoprost 10.

  DOI：

  10.1021/jo00007a052
• 作为产物：
  描述：

  Methyl 7-formyl-4Z-heptenoate 生成 methyl 8-(2-furanyl)-8-hydroxy-4(Z)-octenoate
  参考文献：
  名称：

  J. Org. Chem. 1991, 56, 2549-2552

  摘要：

  DOI：

文献信息

• Process for preparing optically active cyclopentenones
  申请人：SUMITOMO CHEMICAL COMPANY, LIMITED

  公开号：EP0440251A2

  公开（公告）日：1991-08-07

  An improved process for preparing an optically active 4-hydroxycyclopentenone of the formula: wherein R is a lower alkyl, the symbol = means a double bond or triple bond, and the * marked carbon is an asymmetric carbon, and the corresponding racemic 4-hydroxycyclopentenone, which are useful as an intermediate for preparing medical or agricultural products, particularly pharmaceutically active prostaglandins, and intermediates for preparing the optically active and/or racemic 4-hydroxycyclopentenone.

  一种制备具有光学活性的式 4-羟基环戊烯酮的改进工艺： 其中 R 为低级烷基，符号 = 表示双键或三键，标记为 * 的碳为不对称碳，以及相应的外消旋 4-羟基环戊烯酮，可用作制备医药或农产品，特别是具有药用活性的前列腺素的中间体，以及制备光学活性和/或外消旋 4-羟基环戊烯酮的中间体。
• DYGOS, JOHN H.;ADAMEK, JOHN P.;BABIAK, KEVIN A.;BEHLING, JAMES R.;MEDIEH,+, J. ORG. CHEM., 56,(1991) N, C. 2549-2552
  作者：DYGOS, JOHN H.、ADAMEK, JOHN P.、BABIAK, KEVIN A.、BEHLING, JAMES R.、MEDIEH,+

  DOI：——

  日期：——
• US5191109A
  申请人：——

  公开号：US5191109A

  公开（公告）日：1993-03-02
• An efficient synthesis of the antisecretory prostaglandin enisoprost
  作者：John H. Dygos、John P. Adamek、Kevin A. Babiak、James R. Behling、John R. Medich、John S. Ng、Joseph J. Wieczorek

  DOI：10.1021/jo00007a052

  日期：1991.3

  A 13-step synthesis of the antisecretory prostaglandin enisoprost was previously reported by Collins et al. 1 in 1983. The reported synthesis involved coupling of enone 6 with a cuprate reagent2 derived from a suitably substituted vinylstannane and cuprous pentyne to give enisoprost 10 in 60% yield after removal of protecting groups and chromatographic purification.Further development work on the synthesis of enisoprost has resulted in an improved method for preparing the key enone precursor 6 as outlined in Scheme I. Use of the trans-vinyl iodide 9 in place of the corresponding vinylstannane derivative and use of dilithiocyanocuprate3 coupling technology resulted in an 85% isolated yield of enisoprost 10 as outlined in Scheme II.Direct conversion of the terminal acetylene 8b into protected enisoprost via a one-pot process has also been accomplished as outlined in Scheme II. This latter modification greatly simplified the process and resulted in a 71% isolated yield of enisoprost 10.
• J. Org. Chem. 1991, 56, 2549-2552
  作者：

  DOI：——

  日期：——