(4R*,1'R*'2'R*)-4-(1,2-Dioxy-1-methyl-4-phenylbutyl)tetrahydro-2-furanone

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (4R*,1'R*'2'R*)-4-(1,2-Dioxy-1-methyl-4-phenylbutyl)tetrahydro-2-furanone
• 英文别名: (4S)-4-[(2S,3S)-2,3-dihydroxy-5-phenylpentan-2-yl]oxolan-2-one
• 化学式: C₁₅H₂₀O₄
• 分子量: 264.321
• InChiKey: JVJWEPACLZIBLB-YDHLFZDLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4R*,1'R*'2'R*)-4-(1,2-Dioxy-1-methyl-4-phenylbutyl)tetrahydro-2-furanone 在 水 、 碳酸氢钠 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 以90%的产率得到(4R*,5R*,1'R*)-Tetrahydro-4-hydroxymethyl-5-(1-hydroxy-3-phenylpropyl)-5-methyl-2-furanone
  参考文献：
  名称：

  Hydroxyl-Directed Intermolecular Ketone-Olefin Couplings Promoted by SmI2

  摘要：

  SmI2-promoted intermolecular ketone-olefin couplings are facilitated and stereocontrolled by hydroxyl groups incorporated within the starting materials. For example, the SmI2-induced ketone - olefin coupling reactions of alpha-hydroxy ketone 5 with ethyl acrylate, acrylonitrile, ethyl crotonate, and 2(5 H)-furanone proceeded with high stereocontrol to afford the syn-1,2-diol products 6-9 in good yields. Excellent diastereoselectivity was achieved in the reductive couplings of beta-hydroxy aldehyde 21 and erythro-beta-hydroxy ketone 24 with acrylonitrile using SmI2, to produce the anti-1,3-diols 22 and 25 in good yields. The sense of the stereo-selectivity was in full accord with a chelation-control model. In the proposed model, the stereochemistry of the reaction product is explained by assuming that a cyclic ketyl radical is generated during the initial single-electron reduction by SmI2. This radical species results from the chelation of the Sm-III cation, attached to the ketyl radical, with the hydroxyl group.

  DOI：

  10.1002/(sici)1521-3765(19991105)5:11<3252::aid-chem3252>3.0.co;2-d
• 作为产物：
  描述：

  (+/-)-1-(2-Phenylethyl)-3-propynyl acetate 在 samarium diiodide 、 sodium tetrachloroaurate(III) 、 水 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 3.0h， 生成 (4R*,1'R*'2'R*)-4-(1,2-Dioxy-1-methyl-4-phenylbutyl)tetrahydro-2-furanone
  参考文献：
  名称：

  Samarium(II) Iodide Promoted Intermolecular Ketone-Olefin Couplings Chelation-Controlled by .alpha.-Hydroxyl Groups

  摘要：

  The hydroxyl group directed intermolecular ketone-olefin coupling reactions induced by SmI2 between alpha-hydroxyl ketones and alpha,beta-unsaturated esters occurred with excellent stereochemical control about the newly formed asymmetric centers.

  DOI：

  10.1021/jo00102a010

文献信息

• Hydroxyl-Directed Intermolecular Ketone-Olefin Couplings Promoted by SmI2
  作者：Fuyuhiko Matsuda、Motoi Kawatsura、Ken-ichi Hosaka、Haruhisa Shirahama

  DOI：10.1002/(sici)1521-3765(19991105)5:11<3252::aid-chem3252>3.0.co;2-d

  日期：1999.11.5

  SmI2-promoted intermolecular ketone-olefin couplings are facilitated and stereocontrolled by hydroxyl groups incorporated within the starting materials. For example, the SmI2-induced ketone - olefin coupling reactions of alpha-hydroxy ketone 5 with ethyl acrylate, acrylonitrile, ethyl crotonate, and 2(5 H)-furanone proceeded with high stereocontrol to afford the syn-1,2-diol products 6-9 in good yields. Excellent diastereoselectivity was achieved in the reductive couplings of beta-hydroxy aldehyde 21 and erythro-beta-hydroxy ketone 24 with acrylonitrile using SmI2, to produce the anti-1,3-diols 22 and 25 in good yields. The sense of the stereo-selectivity was in full accord with a chelation-control model. In the proposed model, the stereochemistry of the reaction product is explained by assuming that a cyclic ketyl radical is generated during the initial single-electron reduction by SmI2. This radical species results from the chelation of the Sm-III cation, attached to the ketyl radical, with the hydroxyl group.
• Samarium(II) Iodide Promoted Intermolecular Ketone-Olefin Couplings Chelation-Controlled by .alpha.-Hydroxyl Groups
  作者：Motoi Kawatsura、Fuyuhiko Matsuda、Haruhisa Shirahama

  DOI：10.1021/jo00102a010

  日期：1994.11

  The hydroxyl group directed intermolecular ketone-olefin coupling reactions induced by SmI2 between alpha-hydroxyl ketones and alpha,beta-unsaturated esters occurred with excellent stereochemical control about the newly formed asymmetric centers.