cis-2-methyl-2,3-dihydro-4H-pyran-4-ol | 80754-66-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: cis-2-methyl-2,3-dihydro-4H-pyran-4-ol
• 英文别名: cis-2,3-dihydro-2-methylpyran-4-ol；4,6-dideoxy-DL-glucal；(2S,4R)-2-methyl-3,4-dihydro-2H-pyran-4-ol
• CAS: 80754-66-1
• 化学式: C₆H₁₀O₂
• 分子量: 114.144
• InChiKey: LSPXXBIMOLFCIX-WDSKDSINSA-N

物化性质

• 沸点：
  198.1±29.0 °C(Predicted)
• 密度：
  1.059±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.67
• 重原子数：
  8.0
• 可旋转键数：
  0.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  cis-2-methyl-2,3-dihydro-4H-pyran-4-ol 在 四氧化锇 、 硫酸 、 sodium hydride 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 为溶剂， 反应 79.0h， 生成 α-methylchalcoside
  参考文献：
  名称：

  A simple synthesis of dl-chalcose

  摘要：

  DOI：

  10.1021/jo00347a053
• 作为产物：
  描述：

  2-methyl-2,3-dihydro-4H-pyran-4-one 在 sodium tetrahydroborate 、 cerium(III) chloride 作用下， 以 甲醇 为溶剂， 以100%的产率得到cis-2-methyl-2,3-dihydro-4H-pyran-4-ol
  参考文献：
  名称：

  Varelis, Peter; Graham, Alan J.; Johnson, Brian L., Australian Journal of Chemistry, 1994, vol. 47, # 9, p. 1735 - 1740

  摘要：

  DOI：

文献信息

• Limitations in the application of anionic oxy-cope sigmatropy to elaboration of the forskolin nucleus
  作者：Leo A. Paquette、Jeffrey A. Oplinger

  DOI：10.1016/0040-4020(89)80038-9

  日期：1989.1

  conditions to the thermodynanlic enolate 19. This intermediate has been Crapped with several electrophiles, the most relevant to elaboration of the forskolln nucleus being phenylselenenyl chloride. A route Co tricyclic ketones 25 and 26 Is thereby opened. In an attempt to expand upon this chemistry, several more highly functionallzed 3,4-dlhydro-2H-pyrans were prepared; some were obtained in enantiomerlcally

  已在2,4,4-三甲基-2-环己烯酮的四个步骤中合成了功能化的blcyclo [2.2.2]辛烯酮6。该酮与6-lithlodlhydropyran进行1,2-加成，以1：1.8的比例输送醇16和17。17的钾盐在回流的含18-crown-6的四氢呋喃溶液中经历了氧-Cope重排，并在这些条件下产生了热力强的烯醇酸酯19。是苯基硒烯基氯。由此打开路线Co三环酮25和26。为了扩大这种化学性质，制备了一些更高官能度的3，4-二氢-2H-吡喃。由于它们源自碳水化合物前体，因此它们以对映体纯的状态获得。描绘了与在C-6处这些杂环的金属化相关的复杂性。由于在合成的那些加合物（4142、46和51）中未观察到氧阴离子Cope重排的迹象，因此我们得出结论，空间（或可能是电子）影响对该键具有特别强的速率延迟作用[3,3]。渐进式步骤。
• Regiochemical control of the ring opening of 1,2-epoxides by means of chelating processes. Part 17: Synthesis and opening reactions of cis- and trans-oxides derived from (2S,6R)-2-benzyloxy-6-methyl-3,6-dihydro-2H-pyran, (2R,6R)- and (2S,6R)-2-methoxy-6-methyl-5,6-dihydro-2H-pyran
  作者：Paolo Crotti、Valeria Di Bussolo、Lucilla Favero、Franco Macchia、Mauro Pineschi

  DOI：10.1016/s0040-4020(02)00578-1

  日期：2002.7

  The regiochemical behavior of the title deoxy anhydrosugars, prepared in an enantioselective way starting from methyl α-d-glucopyranoside, was examined in opening reactions, both under standard and chelating conditions. The results clearly indicate the influence of the reaction conditions and the importance of the relative orientation of the methyl group with respect to the oxirane ring on the regiochemical

  在标准和螯合条件下，在开放反应中检查了以对映选择性方式从甲基α-d-吡喃葡萄糖苷开始制备的标题脱氧脱水糖的区域化学行为。结果清楚地表明了反应条件的影响以及甲基相对于环氧乙烷环的相对取向的重要性对这些环氧化物的区域化学结果的影响。在某些情况下，可以获得区域选择性的有效反转。
• Enzymatic resolution of racemic glycals: an application of the wong acylation method
  作者：David B. Berkowitz、Samuel J. Danishefsky

  DOI：10.1016/0040-4039(91)80067-g

  日期：1991.9

  Kinetic resolution of racemic, fully synthetic, artificial glycals bearing a free hydroxyl group at C3 was accomplished through the more rapid acylation of the ''D''-antipode with vinyl acetate as acyl donor and Lipase PS-30 from Pseudomonas cepacia as catalyst.
• Synthesis of C1-alkyl- and acylglycals from glycals using a B-alkyl Suzuki–Miyaura cross coupling approach
  作者：Justin S. Potuzak、Derek S. Tan

  DOI：10.1016/j.tetlet.2003.12.006

  日期：2004.2

  A B-alkyl Suzuki-Miyaura cross coupling approach provides a flexible, efficient means to convert glycals to Cl-alkyl-glycals and Cl-acylglycals that are versatile synthetic intermediates. This approach uses readily available glycal starting materials and overcomes major limitations associated with direct alkylation or acylation of glycals. Further, a commonly observed side reaction involving reduction of the halide coupling partner is suppressed by preincubation of the borane coupling partner with aqueous base, providing new mechanistic insights into the side reaction. (C) 2003 Elsevier Ltd. All rights reserved.
• PAQUETTE, LEO A.;OPLINGER, JEFFREY A., TETRAHEDRON, 45,(1989) N 1, C. 107-124
  作者：PAQUETTE, LEO A.、OPLINGER, JEFFREY A.

  DOI：——

  日期：——