(furan-2-yl)methyl 4-methylbenzoate | 4330-24-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (furan-2-yl)methyl 4-methylbenzoate
• 英文别名: 4-methyl-benzoic acid furfuryl ester；2-Furylmethyl 4-methylbenzoate；furan-2-ylmethyl 4-methylbenzoate
• CAS: 4330-24-9
• 化学式: C₁₃H₁₂O₃
• mdl: MFCD01837714
• 分子量: 216.236
• InChiKey: BYPWJBLMJWKUNT-UHFFFAOYSA-N

物化性质

• 熔点：
  49-50.5 °C
• 沸点：
  319.2±22.0 °C(Predicted)
• 密度：
  1.155±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.153
• 拓扑面积：
  39.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-deoxy-D-ribose 在 吡啶 、 盐酸 作用下， 以 氘代氯仿 为溶剂， 反应 1.42h， 生成 (furan-2-yl)methyl 4-methylbenzoate
  参考文献：
  名称：

  2-Deoxy-3,5-di-Op-toluoyl-α-D-erythro-pentofuranosyl Chloride 的方便制备

  摘要：

  摘要 采用乙酰氯作为HCl发生剂，显着改进了α-氯糖4a的Hoffer制备工艺。通过使用 NOE 测量确认了氯原子的 α-构型。研究了 4a 到 β-端基异构体和糠基衍生物 6 的顺序转化。

  DOI：

  10.1080/00397919708007071

文献信息

• HMF and furfural: Promising platform molecules in rhodium-catalyzed carbonylation reactions for the synthesis of furfuryl esters and tertiary amides
  作者：Xinxin Qi、Rong Zhou、Han-Jun Ai、Xiao-Feng Wu

  DOI：10.1016/j.jcat.2019.11.008

  日期：2020.1

  esters and tertiary amides has been developed. 5-Hydroxymethylfurfural (HMF) was used as both substrate and CO surrogate for the first time in a carbonylation reaction, and both alkyl and aryl iodides were tolerated well to afford the desired furfuryl esters in moderate to good yields. In addition, furfural was also utilized as a CO source for the synthesis of tertiary amides. A variety of tertiary amides

  已经开发了涉及铑催化的糠基酯和叔酰胺的羰基合成的生物质。在羰基化反应中，首次使用5-羟甲基糠醛（HMF）作为底物和CO替代物，烷基碘和芳基碘均耐受良好，以中等至良好的收率提供了所需的糠酸酯。另外，糠醛也用作合成叔酰胺的一氧化碳来源。以中等至优异的产率获得了具有良好官能团相容性的多种叔酰胺。值得注意的是，在不存在其他氧化剂的情况下，叔胺通过C N键裂解途径用作胺源。
• An efficient method for the synthesis of aromatic C-nucleosides
  作者：Narayan C. Chaudhuri、Eric T. Kool

  DOI：10.1016/0040-4039(95)00145-3

  日期：1995.3

  Reaction of diarylcadmium or diarylzinc reagents with 1,2-dideoxy-3,5-di-O-p-toluoyl-1-chloro-α-D-ribofuranose affords 3,5-di-O-protected aromatic C-nucleosides in good yields.

  diarylcadmium或diarylzinc试剂的反应用1,2-二脱氧-3,5-二- ø - p甲苯甲酰-1-氯-α-d呋喃核糖，得到3,5-二- ø -保护的芳族C-核苷在良好产量。
• Sonogashira reactions of α- and β-1-ethynyl-2-deoxyribosides: synthesis of acetylene-extended C-nucleosides
  作者：Tomáš Bobula、Michal Hocek、Martin Kotora

  DOI：10.1016/j.tet.2009.11.030

  日期：2010.1

  An improved practical protocol for the synthesis of both anomers of 1-ethynyl-2-deoxiribosides 1 was developed. The Sonogashira coupling of ethynyldeoxyribosides 1 with various aryl- and heteroaryl halides was carried out under various conditions. It was found that the use of copper-free coupling protocols could reduce the oxidative dimerisation in favour of arylalkynyldeoxyriboside formation. (C) 2009 Elsevier Ltd. All rights reserved.
• Harris, Roger; Pfleiderer, Wolfgang, Liebigs Annalen der Chemie, 1981, # 8, p. 1457 - 1468
  作者：Harris, Roger、Pfleiderer, Wolfgang

  DOI：——

  日期：——
• Convenient Preparation of 2-Deoxy-3,5-di-O-<i>p</i>-toluoyl-α-D-<i>erythro</i>-pentofuranosyl Chloride
  作者：Valérie Rolland、Mitsuharu Kotera、Jean Lhomme

  DOI：10.1080/00397919708007071

  日期：1997.10.1

  acetyl chloride as HCl generator, the procedure for the Hoffer preparation of the α-chloro sugar 4a was significantly improved. The α-configuration of the chloro atom was confirmed by using NOE measurement. Sequential transformation of 4a to the β-anomer and to the furfuryl derivative 6 was studied.

  摘要 采用乙酰氯作为HCl发生剂，显着改进了α-氯糖4a的Hoffer制备工艺。通过使用 NOE 测量确认了氯原子的 α-构型。研究了 4a 到 β-端基异构体和糠基衍生物 6 的顺序转化。