2-Hydroxymethyl-cyclooctan-1-carbonsaeure-lacton | 99172-53-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: 2-Hydroxymethyl-cyclooctan-1-carbonsaeure-lacton
• 英文别名: 4,5,6,7,8,9-hexahydrocycloocta[c]furan-1(3H)-one；4,5,6,7,8,9-hexahydro-1H-cycloocta[c]furan-3-one
• CAS: 99172-53-9
• 化学式: C₁₀H₁₄O₂
• 分子量: 166.22
• InChiKey: OIBXRZXMYKDUEM-UHFFFAOYSA-N

物化性质

• 沸点：
  137-139 °C(Press: 0.7 Torr)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 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：

  2-Hydroxymethyl-cyclooctan-1-carbonsaeure-lacton 在 氯化铵-d4 、 lithium dimethylcuprate 作用下， 以 乙醚 为溶剂， 以116.3 mg的产率得到3-deuterio-4,5,6,7,8,9-hexahydrocycloocta[c]furan-1(3H)-one
  参考文献：
  名称：

  Cyclopropanation/Reduction of a 3,4-Disubstituted 2(5H)-Furanone:  A Model for C-8 Methylation at the Taxane BC Ring Juncture

  摘要：

  A cyclopropanation/reduction strategy is described that should prove useful for incorporation of the C-8 methyl group at the taxane BC ring juncture. Treatment of model 2(5H)-furanone 6 with various organocopper-based reagents resulted in gamma-deprotonation to the furan oxide rather than the desired conjugate addition. This pathway was established by deuteration studies. Reaction of 6 with dimethylsulfoxonium methylide in DMSO at room temperature also led exclusively to gamma-deprotonation; however, the use of excess methylide at 50 degrees C led to the clean formation of the desired cyclopropanated adduct 13. While the cyclopropane ring in 13 proved resistant to various heterogeneous hydrogenation conditions, treatment with Li/liq NH3 under careful;temperature control(-78 degrees C to -63 degrees C) led to the regioselective formation of the desired ring-opened product 7 with high (16:1) diastereoselectivity.

  DOI：

  10.1021/jo970564u
• 作为产物：
  描述：

  10-chloro-9-oxodecanoic acid 在 dimsyl sodium 、 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 4.0h， 生成 2-Hydroxymethyl-cyclooctan-1-carbonsaeure-lacton
  参考文献：
  名称：

  大环内酯内的环戊醛缩合：8元碳环的一种新方法。

  摘要：

  已经开发出一种用于构造8元碳环的新方法，该方法涉及作为关键步骤的在11元酮内酯环内的化学选择性的跨环醛醇缩合。

  DOI：

  10.1016/s0040-4039(00)88469-5

文献信息

• Palladium-catalyzed, carbonylative, intramolecular coupling of hydroxyvinyl triflates. Synthesis of substituted .alpha.,.beta.-butenolides
  作者：Geoffrey T. Crisp、Adam G. Meyer

  DOI：10.1021/jo00051a055

  日期：1992.12
• An unusual palladium-catalyzed carbonylative cyclization of β-bromovinyl aldehydes leading to lactones
  作者：Chan Sik Cho、Hyung Sup Shim

  DOI：10.1016/j.tetlet.2006.03.184

  日期：2006.6

  beta-Bromovinyl aldehydes are carbonylatively cyclized under carbon monoxide pressure in MeCN at 100 degrees C in the presence of a catalytic amount of a palladium catalyst along with a base to give the corresponding lactones in high yields. (c) 2006 Elsevier Ltd. All rights reserved.
• Molkentin, Joachim; Goepfert, Andreas; Tochtermann, Werner, Chemische Berichte, 1991, vol. 124, # 8, p. 1875 - 1877
  作者：Molkentin, Joachim、Goepfert, Andreas、Tochtermann, Werner

  DOI：——

  日期：——
• Transannular aldol condensations within macrocyclic lactones: A novel approach to 8-membered carbocyclic rings.
  作者：Mohammad R. Karim、Paul Sampson

  DOI：10.1016/s0040-4039(00)88469-5

  日期：1988.1

  A novel method has been developed for the construction of 8-membered carbocyclic rings, involving as the key step a chemoselective transannular aldol condensation within an 11-membered ketolactone ring.

  已经开发出一种用于构造8元碳环的新方法，该方法涉及作为关键步骤的在11元酮内酯环内的化学选择性的跨环醛醇缩合。
• Cyclopropanation/Reduction of a 3,4-Disubstituted 2(5<i>H</i>)-Furanone:  A Model for C-8 Methylation at the Taxane BC Ring Juncture
  作者：Thomas E. Janini、Paul Sampson

  DOI：10.1021/jo970564u

  日期：1997.7.1

  A cyclopropanation/reduction strategy is described that should prove useful for incorporation of the C-8 methyl group at the taxane BC ring juncture. Treatment of model 2(5H)-furanone 6 with various organocopper-based reagents resulted in gamma-deprotonation to the furan oxide rather than the desired conjugate addition. This pathway was established by deuteration studies. Reaction of 6 with dimethylsulfoxonium methylide in DMSO at room temperature also led exclusively to gamma-deprotonation; however, the use of excess methylide at 50 degrees C led to the clean formation of the desired cyclopropanated adduct 13. While the cyclopropane ring in 13 proved resistant to various heterogeneous hydrogenation conditions, treatment with Li/liq NH3 under careful;temperature control(-78 degrees C to -63 degrees C) led to the regioselective formation of the desired ring-opened product 7 with high (16:1) diastereoselectivity.