D-idono-1,4-lactone | 161168-87-2

• 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: D-idono-1,4-lactone
• 英文别名: D-idonic acid-4-lactone；D-Idonsaeure-4-lacton；D-Idonsaeure-lacton；(3S,4S,5S)-5-((R)-1,2-Dihydroxyethyl)-3,4-dihydroxydihydrofuran-2(3H)-one；(3S,4S,5S)-5-[(1R)-1,2-dihydroxyethyl]-3,4-dihydroxyoxolan-2-one
• CAS: 161168-87-2
• 化学式: C₆H₁₀O₆
• 分子量: 178.142
• InChiKey: SXZYCXMUPBBULW-STGXQOJASA-N

物化性质

• 熔点：
  174 °C
• 沸点：
  467.9±18.0 °C(Predicted)
• 密度：
  1.766±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 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：

  D-idono-1,4-lactone 在 sodium tetrahydroborate 、 ion exchange resin (IR-120, H+) 、 氢溴酸 作用下， 以 水 为溶剂， 反应 1.75h， 生成 6-bromo-6-deoxy-D-iditol
  参考文献：
  名称：

  Enantiomerically pure, highly functionalized tetrahydrofurans from simple carbohydrate precursors

  摘要：

  6-Bromo-6-deoxy-1,4-aldonolactones and 6-bromo-6-deoxy-alditols with D-galacto-, D-altro-, D-manno- and D-ido-configuration were selectively converted into hydroxylated tetrahydrofuran derivatives by simple heating in water. The 6-bromo-6-deoxy-D-altritol (10) and 6-bromo-6-deoxy-D-iditol (25) reacted even at room temperature. Likewise, the 6-bromo-2,6-dideoxy-aldonolactones with D-arabino- (29) and D-lyxo-configuration (31) gave the corresponding 2-deoxy-3,6-anhydrides, when heated in water. The rate of formation of the furan ring by intramolecular nucleophilic substitution was determined by the conformation of the bromopolyols in water.

  DOI：

  10.1016/s0040-4020(01)89337-6
• 作为产物：
  描述：

  (3R,4R,5R)-5-[(1R)-1,2-二羟基乙基]-3,4-二羟基四氢呋喃-2-酮 在 吡啶 、 水 作用下， 生成 D-idono-1,4-lactone
  参考文献：
  名称：

  The Reduction of 5-Keto-D-gluconic Acid with Sodium Borohydride¹

  摘要：

  DOI：

  10.1021/ja01642a056

文献信息

• Rehorst; Naumann, Chemische Berichte, 1944, vol. 77/79, p. 24,29
  作者：Rehorst、Naumann

  DOI：——

  日期：——
• Improvements in the Preparation of L-Tartaric Acid from Racemic Tartaric Acid through Resolution by a Substituted Benzimidazole Base
  作者：W. T. Haskins、C. S. Hudson

  DOI：10.1021/ja01874a076

  日期：1939.5
• FLEET, GEORGE W. J.;RAMSDEN, NIGEL G.;WITTY, DAVID R., TETRAHEDRON LETT., 29,(1988) N 23, 2871-2874
  作者：FLEET, GEORGE W. J.、RAMSDEN, NIGEL G.、WITTY, DAVID R.

  DOI：——

  日期：——
• Enantiomerically pure, highly functionalized tetrahydrofurans from simple carbohydrate precursors
  作者：Inge Lundt、Holger Frank

  DOI：10.1016/s0040-4020(01)89337-6

  日期：1994.1

  6-Bromo-6-deoxy-1,4-aldonolactones and 6-bromo-6-deoxy-alditols with D-galacto-, D-altro-, D-manno- and D-ido-configuration were selectively converted into hydroxylated tetrahydrofuran derivatives by simple heating in water. The 6-bromo-6-deoxy-D-altritol (10) and 6-bromo-6-deoxy-D-iditol (25) reacted even at room temperature. Likewise, the 6-bromo-2,6-dideoxy-aldonolactones with D-arabino- (29) and D-lyxo-configuration (31) gave the corresponding 2-deoxy-3,6-anhydrides, when heated in water. The rate of formation of the furan ring by intramolecular nucleophilic substitution was determined by the conformation of the bromopolyols in water.
• The Reduction of 5-Keto-D-gluconic Acid with Sodium Borohydride¹
  作者：J. K. Hamilton、F. Smith

  DOI：10.1021/ja01642a056

  日期：1954.7