(4R,6S)-6-Methoxycarbonylmethyl-2,2,4-trimethyl-1,3-dioxolane | 139402-27-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4R,6S)-6-Methoxycarbonylmethyl-2,2,4-trimethyl-1,3-dioxolane
• 英文别名: methyl 2-[(4S,6R)-2,2,6-trimethyl-1,3-dioxan-4-yl]acetate
• CAS: 139402-27-0
• 化学式: C₁₀H₁₈O₄
• 分子量: 202.251
• InChiKey: TZKQEUMSVVEJTQ-SFYZADRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  己酸,5-羟基-3-羰基-,1,1-二甲基乙基酯,(S)- 、 2,2-二甲氧基丙烷 在 4-甲基苯磺酸吡啶 、 tetramethylammonium triacetoxyborohydride 作用下， 生成 (4R,6S)-6-Methoxycarbonylmethyl-2,2,4-trimethyl-1,3-dioxolane
  参考文献：
  名称：

  Asymmetric hydrogenation of 3,5-Dioxoesters catalyzed by Ru-binap complex: A short step asymmetric synthesis of 6-substituted 5,6-dihydro-2-pyrones

  摘要：

  Asymmetric hydrogenation of 3,5-dioxoesters 1a-c using Ru2Cl4((R) or (S)-binap)2(NEt3) as the catalyst gave dominantly anti 3,5-dihydroxyesters 2, which were then converted into unsaturated lactones 5a-b (ca. 80% e.e.). The pathway of the hydrogenation reaction was also investigated by asymmetric hydrogenation of (R)- or (S)-5-hydroxy-3-oxoesters 8a-c. It was revealed that the Ru-binap catalyzed hydrogenation of 1a-b proceed dominantly via the beta-diketone mode. A convenient asymmetric synthesis of hydroxylactone 3c and unsaturated lactone 5c was presented.

  DOI：

  10.1016/s0040-4020(01)86300-6

文献信息

• Asymmetric hydrogenation of methyl 3,5-dioxohexanoate catalyzed by ru-binap complex: a short step asymmetric synthesis of dihydro-60methyl-2-H-pyran-2-one
  作者：Liming Shao、Toshiyuki Seki、Hiroyuki Kawano、Masahiko Saburi

  DOI：10.1016/0040-4039(91)80569-r

  日期：1991.12

  Hydrogenation of methyl 3,5-dioxohexanoate 3 using Ru2Cl4((R) or (S)-binap)2(NEt3) as the catalyst gave dominantly anti 3,5-dihydroxyester 9, which was then converted into unsaturated lactone 4. The pathway of the hydrogenation reaction was also investigated.
• One-Pot and Sequential Asymmetric Hydrogenation of β,δ-Diketoesters into Functionalized 1,3-Diols: Fromanti- tosyn-Stereoselectivity
  作者：Véronique Blandin、Jean-François Carpentier、André Mortreux

  DOI：10.1002/(sici)1099-0690(199912)1999:12<3421::aid-ejoc3421>3.0.co;2-1

  日期：1999.12