(+/-)-trans-2,5-bis(methoxycarbonyl)tetrahydrofuran | 81340-21-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (+/-)-trans-2,5-bis(methoxycarbonyl)tetrahydrofuran
• 英文别名: dimethyl (2S,5S)-oxolane-2,5-dicarboxylate
• CAS: 81340-21-8
• 化学式: C₈H₁₂O₅
• 分子量: 188.18
• InChiKey: LPLJNEHCXHAFLB-WDSKDSINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (+/-)-trans-2,5-bis(methoxycarbonyl)tetrahydrofuran 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 12.0h， 以82%的产率得到trans-2,5-bis(hydroxymethyl)tetrahydrofuran
  参考文献：
  名称：

  Synthesis of stereoisomeric crown ethers composed of cis- and trans-2,5-bis(hydroxymethyl)tetrahydrofuran units and their selective transport of alkali metal cations through liquid membranes

  摘要：

  DOI：

  10.1021/jo00133a038
• 作为产物：
  描述：

  重氮甲烷 、 Tetrahydrofuran-(+/-)-trans-2,5-dicarbonsaeure 以 乙醚 为溶剂， 以95%的产率得到(+/-)-trans-2,5-bis(methoxycarbonyl)tetrahydrofuran
  参考文献：
  名称：

  Synthesis of stereoisomeric crown ethers composed of cis- and trans-2,5-bis(hydroxymethyl)tetrahydrofuran units and their selective transport of alkali metal cations through liquid membranes

  摘要：

  DOI：

  10.1021/jo00133a038

文献信息

• Enzyme-catalyzed asymmetric acylation and hydrolysis of cis-2,5-disubstituted tetrahydrofuran derivatives: Contribution to development of models for reactions catalyzed by porcine liver esterase and porcine pancreatic lipase
  作者：Koichiro Naemura、Ritsuko Fukuda、Nobuo Takahashi、Masayoshi Konishi、Yoshiki Hirose、Yoshito Tobe

  DOI：10.1016/s0957-4166(00)80131-7

  日期：1993.5

  Pig liver esterase, lipase from porcine pancreas, lipase from Pseudomonas sp. (lipase YS), and lipase from Candida cylindracea catalyzed hydrolyses of the cis-diacetate 1 and the trans-diacetate (+/-)-4 to give the cis-monoacetate 3 and the trans-monoacetate 6 in optically active forms, respectively. Lipase YS-catalyzed acylations of the cis-diol 2 and the trans-diol (+/-)-5 with an acylating agent in cyclohexane yielded (-)-3 and (-)-6, respectively. The group adjacent to the R stereogenic center preferentially reacted in lipase YS-catalyzed hydrolyses of 1 and (+/-)-4 and acylations of 2 and (+/-)-5, and the enantioselectivities are rationalized by our rule recently proposed for lipase YS.
• Synthesis of stereoisomeric crown ethers composed of cis- and trans-2,5-bis(hydroxymethyl)tetrahydrofuran units and their selective transport of alkali metal cations through liquid membranes
  作者：Masao Nakazaki、Koichiro Naemura、Masaru Makimura、Atsushi Matsuda、Takaaki Kawano、Yoshihiro Ohta

  DOI：10.1021/jo00133a038

  日期：1982.6