(R)-ethyl 1-(1-hydroxyethyl)cyclopent-3-ene-1-carboxylate | 1315590-12-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: (R)-ethyl 1-(1-hydroxyethyl)cyclopent-3-ene-1-carboxylate
• 英文别名: SRC 491；ethyl 1-[(1R)-1-hydroxyethyl]cyclopent-3-ene-1-carboxylate
• CAS: 1315590-12-5
• 化学式: C₁₀H₁₆O₃
• 分子量: 184.235
• InChiKey: ZLDMKDKJRHWUDB-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-ethyl 1-(1-hydroxyethyl)cyclopent-3-ene-1-carboxylate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 21.0~22.0 ℃ 、101.33 kPa 条件下， 反应 20.0h， 以91%的产率得到(R)-ethyl 1-(1-hydroxyethyl)cyclopentanecarboxylate
  参考文献：
  名称：

  An Unexpected Directing Effect in the Asymmetric Transfer Hydrogenation of α,α-Disubstituted Ketones

  摘要：

  alpha,alpha-Disubstituted ketones containing an aromatic ring or alkene are reduced in high enantiomeric excess using an asymmetric transfer hydrogenation catalyst. The sense of reduction indicates that the unsaturated region of the ketone adopts a position adjacent to the Ru-bound eta(6)-arene ring in the reduction transition state.

  DOI：

  10.1021/ol201643v
• 作为产物：
  描述：

  ethyl 1-acetylcyclopent-3-ene-1-carboxylate 在 甲酸 、 N-[(1R,2R)-1,2-diphenyl-2-(3-phenylpropylamino)ethyl]-4-methylbenzene sulfonamide ammonium chloride ruthenium 、 三乙胺 作用下， 反应 30.0h， 以89%的产率得到(R)-ethyl 1-(1-hydroxyethyl)cyclopent-3-ene-1-carboxylate
  参考文献：
  名称：

  An Unexpected Directing Effect in the Asymmetric Transfer Hydrogenation of α,α-Disubstituted Ketones

  摘要：

  alpha,alpha-Disubstituted ketones containing an aromatic ring or alkene are reduced in high enantiomeric excess using an asymmetric transfer hydrogenation catalyst. The sense of reduction indicates that the unsaturated region of the ketone adopts a position adjacent to the Ru-bound eta(6)-arene ring in the reduction transition state.

  DOI：

  10.1021/ol201643v

文献信息

• An Unexpected Directing Effect in the Asymmetric Transfer Hydrogenation of α,α-Disubstituted Ketones
  作者：Rina Soni、John-Michael Collinson、Guy C. Clarkson、Martin Wills

  DOI：10.1021/ol201643v

  日期：2011.8.19

  alpha,alpha-Disubstituted ketones containing an aromatic ring or alkene are reduced in high enantiomeric excess using an asymmetric transfer hydrogenation catalyst. The sense of reduction indicates that the unsaturated region of the ketone adopts a position adjacent to the Ru-bound eta(6)-arene ring in the reduction transition state.