7-deoxy-L-glycero-L-talo-heptono-1,4-lactone | 161721-49-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 7-deoxy-L-glycero-L-talo-heptono-1,4-lactone
• 英文别名: γ lactone of l-rhamno-β-hexonic acid；γ-Lacton der l-Rhamno-β-hexonsaeure；(3R,4S,5R)-5-[(1S,2S)-1,2-dihydroxypropyl]-3,4-dihydroxyoxolan-2-one
• CAS: 161721-49-9
• 化学式: C₇H₁₂O₆
• 分子量: 192.169
• InChiKey: AELVIFBFKYHPQO-FQJSGBEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  107
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  丙酮 、 7-deoxy-L-glycero-L-talo-heptono-1,4-lactone 在 camphor-10-sulfonic acid 、 2,2-二甲氧基丙烷 作用下， 生成 7-deoxy-2,3:5,6-di-O-isopropylidene-L-glycero-L-talo-heptono-1,4-lactone
  参考文献：
  名称：

  Ketals of L-rhamnoheptonolactones: Potential mimics of L-rhamnose

  摘要：

  Isopropylidene and cyclohexylidene ketals of gamma- and delta-heptonolactones derived from Kiliani ascensions of protected L-rhamnose may constitute suitable intermediates for the preparation of mimics of L-rhamnose. The X-ray crystal structure of 7-deoxy-3,4-O-isopropylidene-1-glycero-1-galacto-hepta 1,5-lactone provides an example of a delta-lactone in a boat conformation with a substituent in a flagpole position. The size of ring in the lactones is completely consistent with Hudson's classical lactone rotation rule of 1910.

  DOI：

  10.1016/s0957-4166(00)80399-7
• 作为产物：
  描述：

  3,4-O-cyclohexylidene-7-deoxy-L-glycero-L-talo-heptono-1,5-lactone 在 三氟乙酸 作用下， 反应 3.0h， 以46%的产率得到7-deoxy-L-glycero-L-talo-heptono-1,4-lactone
  参考文献：
  名称：

  Ketals of L-rhamnoheptonolactones: Potential mimics of L-rhamnose

  摘要：

  Isopropylidene and cyclohexylidene ketals of gamma- and delta-heptonolactones derived from Kiliani ascensions of protected L-rhamnose may constitute suitable intermediates for the preparation of mimics of L-rhamnose. The X-ray crystal structure of 7-deoxy-3,4-O-isopropylidene-1-glycero-1-galacto-hepta 1,5-lactone provides an example of a delta-lactone in a boat conformation with a substituent in a flagpole position. The size of ring in the lactones is completely consistent with Hudson's classical lactone rotation rule of 1910.

  DOI：

  10.1016/s0957-4166(00)80399-7

文献信息

• Fischer,E.; Morrell, Chemische Berichte, 1894, vol. 27, p. 387
  作者：Fischer,E.、Morrell

  DOI：——

  日期：——
• Ketals of L-rhamnoheptonolactones: Potential mimics of L-rhamnose
  作者：Joseph R. Wheatley、Annabel R. Beacham、Paul M. de Q. Lilley、David J. Watkin、George W.J. Fleet

  DOI：10.1016/s0957-4166(00)80399-7

  日期：1994.12

  Isopropylidene and cyclohexylidene ketals of gamma- and delta-heptonolactones derived from Kiliani ascensions of protected L-rhamnose may constitute suitable intermediates for the preparation of mimics of L-rhamnose. The X-ray crystal structure of 7-deoxy-3,4-O-isopropylidene-1-glycero-1-galacto-hepta 1,5-lactone provides an example of a delta-lactone in a boat conformation with a substituent in a flagpole position. The size of ring in the lactones is completely consistent with Hudson's classical lactone rotation rule of 1910.