methyl (1R)-1-fluoro-2-oxocyclohexane-1-carboxylate | 144462-29-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (1R)-1-fluoro-2-oxocyclohexane-1-carboxylate
• CAS: 144462-29-3
• 化学式: C₈H₁₁FO₃
• 分子量: 174.172
• InChiKey: RTUMZQUWNLXPOW-MRVPVSSYSA-N

物化性质

• 沸点：
  211.9±40.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (1R)-1-fluoro-2-oxocyclohexane-1-carboxylate 在 sodium tetrahydroborate 、 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 8.5h， 生成 [(1S)-1-fluoro-2,2-dimethoxycyclohexyl]methanol
  参考文献：
  名称：

  A novel enantioselective preparation of α-fluoro-β-keto acids

  摘要：

  A two-step method for the enantioselective preparation of alpha-fluorinated beta-keto acids from 1,3-dioxin-4-ones having l-menthone as the chiral auxiliary at the 2-position is described. The method consists of fluorination of the dioxinones by molecular fluorine and solvolytic cleavage of the acetal function.

  DOI：

  10.1016/s0957-4166(00)86035-8
• 作为产物：
  描述：

  在 potassium carbonate 、 fluorine 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 30.0h， 生成 methyl (1R)-1-fluoro-2-oxocyclohexane-1-carboxylate
  参考文献：
  名称：

  A novel enantioselective preparation of α-fluoro-β-keto acids

  摘要：

  A two-step method for the enantioselective preparation of alpha-fluorinated beta-keto acids from 1,3-dioxin-4-ones having l-menthone as the chiral auxiliary at the 2-position is described. The method consists of fluorination of the dioxinones by molecular fluorine and solvolytic cleavage of the acetal function.

  DOI：

  10.1016/s0957-4166(00)86035-8

文献信息

• Enantioselective α-Fluorination and Chlorination of β-Ketoesters by Cobalt Catalyst
  作者：Motoi Kawatsura、Shunsuke Hayashi、Yuji Komatsu、Shuichi Hayase、Toshiyuki Itoh

  DOI：10.1246/cl.2010.466

  日期：2010.5.5

  We demonstrated the cobalt-catalyzed asymmetric α-fluorination and α-chlorination of β-ketoesters. Both reactions were achieved using a catalytic amount of Co(acac)2 with (R,R)-Jacobsen’s salen ligand; α-fluorinated or α-chlorinated products were thus obtained with a good enentioselectivity.

  我们展示了钴催化的不对称 α-氟化和 α-氯化 β-酮酯反应。这两个反应都是使用催化量的 Co(acac)2 与 (R,R)-Jacobsen's salen 配体实现的；从而以良好的烯选择性获得了 α-氟化或 α-氯化产物。
• Asymmetric fluorination of β-keto esters catalyzed by chiral rare earth perfluorinated organophosphates
  作者：Shoko Suzuki、Hiroshi Furuno、Yasuo Yokoyama、Junji Inanaga

  DOI：10.1016/j.tetasy.2005.12.029

  日期：2006.2

  Novel chiral rare earth metal complexes bearing perfluorinated binaphthyl phosphate ligand RE[(R)-F8BNP](3) (RE = rare earth; F8BNP = 5,5',6,6',7,7'.8,8'-octafluoro-1,1'-binaphthyl-2,2-diyl phosphate) have been synthesized and used as a catalyst for the asymmetric electrophilic fluorination reaction of beta-keto esters. The use of Sc[(R)-F8BNP](3) catalyst in combination with 1-fluoropyridinium triflate (NFPY-OTf) as a fluorinating agent was found to give the desired alpha-fluoro-beta-keto esters in high chemical yields and enantiomeric excesses (up to 88% ee) under mild conditions. (c) 2006 Elsevier Ltd. All rights reserved.