trans-6(R)-carbomethoxy-2-methoxy-5,6-dihydro-2H-pyran | 133908-88-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: trans-6(R)-carbomethoxy-2-methoxy-5,6-dihydro-2H-pyran
• 英文别名: methyl (2R,6R)-6-methoxy-3,6-dihydro-2H-pyran-2-carboxylate
• CAS: 133908-88-0
• 化学式: C₈H₁₂O₄
• 分子量: 172.181
• InChiKey: BEPDBZBIHYPLTB-RNFRBKRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  trans-6(R)-carbomethoxy-2-methoxy-5,6-dihydro-2H-pyran 以50%的产率得到
  参考文献：
  名称：

  KONOWAL A.; BELNIAK K.; JURCZAK J.; CHMIELEWSKI O.; ACHMATOWICZ O. JR.; Z+, ROCZ. CHEM. , 1976, 50, NO 3, 505-514

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(methoxycarbonyl)-3,4-dihydro-2H-pyran 在 sodium periodate 、 碳酸氢钠 、 三乙胺 、 calcium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 trans-6(R)-carbomethoxy-2-methoxy-5,6-dihydro-2H-pyran
  参考文献：
  名称：

  取代的3,4-二氢吡喃的alkoxyselenation的立体化学：对于2-烷氧基-5,6-二氢-2的结构的有用的方法ħ -pyrans

  摘要：

  3,4-dihydro-2 H -pyrans烷氧基硒酸化的立体化学已被研究作为鉴定单糖组分新途径的研究的一部分。

  DOI：

  10.1039/c39800000477

文献信息

• Enantioselective Hetero-Diels-Alder reaction with glyoxylate catalyzed by chiral titanium complex: asymmetric synthesis of the lactone portion of mevinolin and compactin
  作者：Masahiro Terada、Koichi Mikami、Takeshi Nakai

  DOI：10.1016/s0040-4039(00)92124-5

  日期：1991.2

  Asymmetric Diels-Alder reaction with methyl glyoxylate catalyzed by the chiral titanium complex 1 provides the dihydropyran carboxylate in high enantiomeric purity, which can be converted to the lactone portion of mevinolin or compactin.

  通过手性钛络合物1催化的乙醛酸甲酯与不对称Diels-Alder反应提供了高对映体纯度的二氢吡喃羧酸盐，其可以转化为美维林或紧密蛋白的内酯部分。
• Asymmetric Catalysis of Diels-Alder Cycloadditions by an MS-Free Binaphthol-Titanium Complex: Dramatic Effect of MS, Linear vs Positive Nonlinear Relationship, and Synthetic Applications
  作者：Koichi Mikami、Yukihiro Motoyama、Masahiro Terada

  DOI：10.1021/ja00086a014

  日期：1994.4

  Asymmetric Diels-Alder (D.-A.) reaction of 5-hydroxynaphthoquinone (juglone) with butadienyl acetate catalyzed by the binaphthol-derived chiral titanium (BINOL-Ti) complex 1 proceeds in only 9% ee in the presence of molecular sieves (MS). Remarkably, however, this reaction proceeds in 76-96% ee with BINOL-Ti complex 1 freed from MS to provide the endo-adducts useful for the synthesis of anthracyclines and tetracyclines. The solid MS-free BINOL-Ti complex 1 is stable for months at -20 degrees C, Enhancements in endo selectivity and asymmetric induction are observed with the MS-free BINOL-Ti 1 also in the catalyzed D.-A. cycloaddition of methacrolein and glyoxylate with 1,3-dienol ethers and esters. The glyoxylate adducts can be converted to the mevinolin (compactin) intermediates. Surprisingly, the MS-free complex 1 exhibits not only a linear relationship between the ee's of BINOL-Ti 1 and the D.-A. products but also a positive nonlinear effect (asymmetric amplification), depending simply on the mixing manner of (R)-1 with (S)-1 or (+/-)-1.