(+/-)-2-ethoxycarbonyl-2,3-dihydro-2-isopropylpyran-4-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (+/-)-2-ethoxycarbonyl-2,3-dihydro-2-isopropylpyran-4-one
• 英文别名: 2-isopropyl-2-ethoxycarbonyl-2,3-dihydro-4H-pyran-4-one；ethyl 4-oxo-2-propan-2-yl-3H-pyran-2-carboxylate
• 化学式: C₁₁H₁₆O₄
• 分子量: 212.246
• InChiKey: BMNYGOVIMCHGND-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  反-1-甲氧基-3-(三甲基硅氧基)-1,3-丁二烯 、 3-甲基-2-氧代丁酰乙酯 在 (+)-2,2'-亚甲基双[(3aR,8aS)-3a,8a-二氢-8H-茚苯[1,2-d]并恶唑 、 scandium tris(trifluoromethanesulfonate) 、 盐酸 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 22.0h， 以18%的产率得到(+/-)-2-ethoxycarbonyl-2,3-dihydro-2-isopropylpyran-4-one
  参考文献：
  名称：

  Chiral dihydropyranones via hetero Diels–Alder reaction of Danishefsky's diene and α-ketoesters: a high-throughput screening approach

  摘要：

  The chiral Lewis acid-catalyzed hetero Diels-Alder reaction between Danishefsky's diene and sterically hindered alpha-ketoesters has been optimized using a validated high-throughput screening method. The yields and enantioselectivities of three chiral dihydropyranones obtained by this multi-substrate one-pot screening approach are in excellent agreement with individual screening results. Employing ethyl benzoylformate, ethyl 3-methyl-2-oxobutyrate, and dihydro-4,4-dimethyl-2,3-furandione in one reaction mixture allowed a fast evaluation of chiral Lewis acid composition, solvent, temperature, catalyst loading, and dienophile concentration. The crude product mixtures were analyzed by HPLC using two chiral stationary phases coupled in series to avoid time-consuming work-up procedures. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.05.024

文献信息

• Binaphthol monophosphoric acid derivative and its use
  申请人：Tosoh Corporation

  公开号：EP1038877A1

  公开（公告）日：2000-09-27

  A binaphthol monophosphoric acid derivative of the following formula (1), (2), (3) or (4): wherein each of R1, R2, R3 and R4 which are independent of one another, is hydrogen, a C1-20 linear or branched alkyl group, a C1-20 linear or branched alkenyl group, a C1-20 linear or branched alkynyl group, a phenyl group, a phenyl group having its nucleus substituted at the 1- to 4-carbon atom by a C1-10 linear or branched alkyl group, a phenyl group having its nucleus substituted at the 1- to 4-carbon atom by a C1-10 linear or branched alkenyl group, a phenyl group having its nucleus substituted at the 1-to 4-carbon atom by a C1-10 linear or branched alkynyl group, a naphthyl group or a C3-8 cycloalkyl group, provided that R1 to R4 are not simultaneously hydrogen, wherein each of R5, R6, R7 and R8 which are independent of one another, is hydrogen, a C1-20 linear or branched alkyl group, a C1-20 linear or branched alkenyl group, a C1-20 linear or branched alkynyl group, a phenyl group, a phenyl group having its nucleus substituted at the 1- to 4-carbon atom by a C1-10 linear or branched alkyl group, a phenyl group having its nucleus substituted at the 1- to 4-carbon atom by a C1-10 linear or branched alkenyl group, a phenyl group having its nucleus substituted at the 1-to 4-carbon atom by a C1-10 linear or branched alkynyl group, a naphthyl group or a C3-8 cycloalkyl group.

  下式(1)、(2)、(3)或(4)的二萘酚单磷酸衍生物： 其中相互独立的 R1、R2、R3 和 R4 各为氢、C1-20 直链或支链烷基、C1-20 直链或支链烯基、C1-20 直链或支链炔基、苯基、其核在 1 至 4 碳原子上被 C1-10 直链或支链烷基取代的苯基、在 1 至 4 碳原子处其核被 C1-10 直链或支链烯基取代的苯基、在 1 至 4 碳原子处其核被 C1-10 直链或支链炔基取代的苯基、萘基或 C3-8 环烷基，条件是 R1 至 R4 不同时为氢、 其中相互独立的 R5、R6、R7 和 R8 各为氢、C1-20 直链或支链烷基、C1-20 直链或支链烯基、C1-20 直链或支链炔基、苯基、其核在 1-4 碳原子上被 C1-10 直链或支链烷基取代的苯基、在 1 至 4 碳原子处其核被 C1-10 直链或支链烯基取代的苯基、在 1 至 4 碳原子处其核被 C1-10 直链或支链炔基取代的苯基、萘基或 C3-8 环烷基。
• US6274745B1
  申请人：——

  公开号：US6274745B1

  公开（公告）日：2001-08-14