(4R,6R)-4,6-dimethyl-2-<3-oxo-(1E)-penten-1-yl>-2-phenyl-1,3-dioxane | 144405-04-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4R,6R)-4,6-dimethyl-2-<3-oxo-(1E)-penten-1-yl>-2-phenyl-1,3-dioxane
• 英文别名: (E)-1-[(4R,6R)-4,6-dimethyl-2-phenyl-1,3-dioxan-2-yl]pent-1-en-3-one
• CAS: 144405-04-9
• 化学式: C₁₇H₂₂O₃
• 分子量: 274.36
• InChiKey: NCWQBIGYMJOKRL-SNESEAJLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  甲基锂 、 (4R,6R)-4,6-dimethyl-2-<3-oxo-(1E)-penten-1-yl>-2-phenyl-1,3-dioxane 在 copper(l) iodide 、 三甲基氯硅烷 作用下， 生成 (4R,6R)-4,6-dimethyl-2-<(R)-4-oxohexan-2-yl>-2-phenyl-1,3-dioxane 、 (4R,6R)-4,6-dimethyl-2-<(S)-4-oxohexan-2-yl>-2-phenyl-1,3-dioxane
  参考文献：
  名称：

  Distinction of diastereofaces at the α-position of chiral cyclic acetals

  摘要：

  Asymmetric 1,2- and 1,4-additions to substrates with an acetal as a chiral auxiliary have been studied. Among the tested substrates, C2-symmetrical 5c was most effective for 1,2-addition with MeTi(O-iPr)3. Furthermore, C2-symmetrical carbinol 5b has been found to be a potent H-1-NMR reagent for determination of optical purity of carboxylic acids with a chiral center at the alpha-position.

  DOI：

  10.1016/s0957-4166(00)86042-5
• 作为产物：
  描述：

  (4R,6R)-2-hydroxymethyl-4,6-dimethyl-2-phenyl-1,3-dioxane 在 草酰氯 、 sodium hydride 、 二甲基亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 1.67h， 生成 (4R,6R)-4,6-dimethyl-2-<3-oxo-(1E)-penten-1-yl>-2-phenyl-1,3-dioxane
  参考文献：
  名称：

  Distinction of diastereofaces at the α-position of chiral cyclic acetals

  摘要：

  Asymmetric 1,2- and 1,4-additions to substrates with an acetal as a chiral auxiliary have been studied. Among the tested substrates, C2-symmetrical 5c was most effective for 1,2-addition with MeTi(O-iPr)3. Furthermore, C2-symmetrical carbinol 5b has been found to be a potent H-1-NMR reagent for determination of optical purity of carboxylic acids with a chiral center at the alpha-position.

  DOI：

  10.1016/s0957-4166(00)86042-5

文献信息

• Distinction of diastereofaces at the α-position of chiral cyclic acetals
  作者：Naoki Tanaka、Hiroshi Suemune、Kiyoshi Sakai

  DOI：10.1016/s0957-4166(00)86042-5

  日期：1992.8

  Asymmetric 1,2- and 1,4-additions to substrates with an acetal as a chiral auxiliary have been studied. Among the tested substrates, C2-symmetrical 5c was most effective for 1,2-addition with MeTi(O-iPr)3. Furthermore, C2-symmetrical carbinol 5b has been found to be a potent H-1-NMR reagent for determination of optical purity of carboxylic acids with a chiral center at the alpha-position.