(R)-(+)-butyl 4,5-dimethyl-3,6-dihydro-2H-pyran-2-carboxylate | 253778-25-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (R)-(+)-butyl 4,5-dimethyl-3,6-dihydro-2H-pyran-2-carboxylate
• 英文别名: n-butyl (R)-4,5-dimethyl-3,6-dihydro-2H-pyran-2-carboxylate；butyl (2R)-4,5-dimethyl-3,6-dihydro-2H-pyran-2-carboxylate
• CAS: 253778-25-5
• 化学式: C₁₂H₂₀O₃
• 分子量: 212.289
• InChiKey: KPEPWLBBARBODG-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2,3-二甲基-1,3-丁二烯 、 乙醛酸正丁酯 在 [(C₆H₁₀)(NCH(C₆H₂)(O)(tBu)2)2Cr]BF₄ 作用下， 以 甲苯 为溶剂， 25.0 ℃ 、100.0 kPa 条件下， 反应 24.0h， 生成 n-butyl 2-hydroxy-5-methyl-4-methylene-5-hexenoate 、 (R)-(+)-butyl 4,5-dimethyl-3,6-dihydro-2H-pyran-2-carboxylate 、 (S)-(+)-butyl 4,5-dimethyl-3,6-dihydro-2H-pyran-2-carboxylate
  参考文献：
  名称：

  手性（Salen）Chromium（III）配合物催化的Buta-1,3-二烯对映选择性[4 + 2]环加成至乙醛酸烷基酯

  摘要：

  丁-1,3-二烯（3），环己-1,3-二烯（5）和2,3-二甲基丁-1,3-二烯（6）的热和高压[4 + 2]环加成反应类型的烷基乙醛酸2（R ñ -Bu，我-Pr，吨-Bu），由铬复合物催化（R，R） - 1，从而导致相应的cycloadducts 4,7和8以相对高的对映选择性，进行了描述。

  DOI：

  10.1002/adsc.200390058

文献信息

• Asymmetric Hetero Diels−Alder Reaction Catalyzed by Chiral Cationic Palladium(II) and Platinum(II) Complexes
  作者：Shuichi Oi、Eiji Terada、Kazuei Ohuchi、Tomoko Kato、Yukari Tachibana、Yoshio Inoue

  DOI：10.1021/jo9906680

  日期：1999.11.1

  The hetero Diels-Alder reaction of nonactivated conjugated dienes 1 with arylglyoxals 2 and glyoxylate esters 7 proceeded enantioselectively in the presence of a catalytic amount of cationic chiral BINAP-palladium or -platinum complexes and 3 Angstrom molecular sieves (MS3A). The addition of MS3A effectively improved the enantioselectivity of the reaction. Excellent ee's were obtained from the reactions of 2,3-dimethyl-1,3-butadiene (1a) and 1,3-cyclohexadiene (1d) with dienophiles 2 and 7. The square-planar structure of [Pd(S-BINAP)(PhCN)(2)](PF6)(2) was determined by X-ray diffraction, and a chiral induction model involving the square-planar palladium complex coordinated with BINAP and a dienophile is proposed.
• The enantioselective Diels–Alder reaction of 1-methoxybuta-1,3-diene with n-butyl glyoxylate catalyzed by the (salen)Cr(III)Cl and Co(II) complexes
  作者：Piotr Kwiatkowski、Monika Asztemborska、Janusz Jurczak

  DOI：10.1016/j.tetasy.2004.08.002

  日期：2004.10

  Commercially available (salen)Cr(III)Cl 4c and (salen)Co(II) 5a complexes were found to promote [4+2]cycloaddition of 1-methoxybuta-1,3-diene 1 to n-butyl glyoxylate 2, affording 6-substituted 2-methoxy-5,6-dihydro-2H-pyrans 3 in good yield and with enantioselectivites of 70-90% ee. The catalyst 5a was also effective in the reaction of Danishefsky's diene 6, piperylene 8 and 2,3-dimethylbuta-1,3-diene 10 with glyoxylate 2, however enantioselectivities were lower. (C) 2004 Elsevier Ltd. All rights reserved.