2-carbobutoxy-3,6-dihydro-2H-pyran | 60900-13-2

• 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-carbobutoxy-3,6-dihydro-2H-pyran
• 英文别名: n-butyl 3,6-dihydro-2H-pyran-2-carboxylate；butyl 3,6-dihydro-2H-pyran-2-carboxylate
• CAS: 60900-13-2
• 化学式: C₁₀H₁₆O₃
• 分子量: 184.235
• InChiKey: OORQVNDBKIXGJD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 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：

  2-carbobutoxy-3,6-dihydro-2H-pyran 在 platinum on activated charcoal 硫酸 、 氢气 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成 四氢吡喃-2-甲酸甲酯
  参考文献：
  名称：

  Carbon-13 NMR spectra of saturated heterocycles: XI—Tetrahydropyrans (oxanes)

  摘要：

  AbstractThe 13C NMR spectra of 62 oxanes (tetrahydropyrans) with and without methyl substituents at various ring positions, some of them bearing in addition (or instead) ethyl, vinyl, ethynyl, carbomethoxy and methylol substituents at C‐2, have been recorded, and the 294 resulting chemical shifts have been correlated by multiple linear regression analysis. Axial and equatorial α‐, β‐, γ‐, δ‐, gem‐ and vic‐parameters for shifts caused by methyl groups at all ring positions, and similar parameters for Et,—CHCH2,—CCH, CO2Me and CH2OH groups at C‐2, are reported. Standard deviations of the parameters are, in most cases, within 0.3 ppm and the agreement of calculated and experimental shifts is excellent. This is probably the largest parameter set of this type extant. 13C NMR spectra of a number of additional substituted tetrahydropyrans, and of 3,6‐dihydro‐2H‐pyrans and 3,4‐dihydro‐2H‐pyrans, are tabulated and discussed.

  DOI：

  10.1002/omr.1270210205
• 作为产物：
  描述：

  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 ℃ 、1000.01 MPa 条件下， 反应 24.0h， 生成 2-carbobutoxy-3,6-dihydro-2H-pyran
  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

• Preparation of 3,6-dihydro-2H-pyran-2-carboxylic esters
  申请人：——

  公开号：US20030158430A1

  公开（公告）日：2003-08-21

  A process is provided for preparing 3,6-dihydro-2H-pyran-2-carboxylic esters via a thermal hetero Diels-Alder reaction of 1,3-dienes with glyoxylic esters without the use of catalysts and stabilizers using a special metering technique.

  本发明提供了一种利用特殊计量技术，在不使用催化剂和稳定剂的情况下，通过 1,3-二烯与乙醛酸酯的热杂环 Diels-Alder 反应制备 3,6-二氢-2H-吡喃-2-羧酸酯的工艺。
• US6884897B2
  申请人：——

  公开号：US6884897B2

  公开（公告）日：2005-04-26
• Carbon-13 NMR spectra of saturated heterocycles: XI—Tetrahydropyrans (oxanes)
  作者：Ernest L. Eliel、Muthiah Manoharan、K. Michal Pietrusiewicz、Karl D. Hargrave

  DOI：10.1002/omr.1270210205

  日期：1983.2

  AbstractThe 13C NMR spectra of 62 oxanes (tetrahydropyrans) with and without methyl substituents at various ring positions, some of them bearing in addition (or instead) ethyl, vinyl, ethynyl, carbomethoxy and methylol substituents at C‐2, have been recorded, and the 294 resulting chemical shifts have been correlated by multiple linear regression analysis. Axial and equatorial α‐, β‐, γ‐, δ‐, gem‐ and vic‐parameters for shifts caused by methyl groups at all ring positions, and similar parameters for Et,—CHCH2,—CCH, CO2Me and CH2OH groups at C‐2, are reported. Standard deviations of the parameters are, in most cases, within 0.3 ppm and the agreement of calculated and experimental shifts is excellent. This is probably the largest parameter set of this type extant. 13C NMR spectra of a number of additional substituted tetrahydropyrans, and of 3,6‐dihydro‐2H‐pyrans and 3,4‐dihydro‐2H‐pyrans, are tabulated and discussed.
• Enantioselective [4+2] Cycloaddition of Buta-1,3-dienes to Alkyl Glyoxylates Catalyzed by the Chiral (Salen)Chromium(III) Complex
  作者：Piotr Kwiatkowski、Monika Asztemborska、Jean-Claude Caille、Janusz Jurczak

  DOI：10.1002/adsc.200390058

  日期：2003.4

  of buta-1,3-diene (3), cyclohexa-1,3-diene (5), and 2,3-dimethylbuta-1,3-diene (6) to alkyl glyoxylates of type 2 ( Rn-Bu, i-Pr, t-Bu), catalyzed by chromium complex (R,R)-1, leading to the corresponding cycloadducts 4, 7 and 8 with relatively high enantioselectivity, are described.

  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。