4,4-(5-oxo-1,3-dioxolane)diacetic acid anhydride | 4767-12-8

• 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: 4,4-(5-oxo-1,3-dioxolane)diacetic acid anhydride
• 英文别名: 5-oxo-1,3-dioxolane-4,4-diacetic anhydride；1,3,8-trioxa-spiro[4.5]decane-4,7,9-trione；1,3,8-Trioxa-spiro[4.5]decan-4,7,9-trion；1,3,8-Trioxaspiro[4.5]decane-4,7,9-trione
• CAS: 4767-12-8
• 化学式: C₇H₆O₆
• 分子量: 186.121
• InChiKey: CKISKMVRUYIEFX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4,4-(5-oxo-1,3-dioxolane)diacetic acid anhydride 生成 ((S)-4-Methoxycarbonylmethyl-5-oxo-[1,3]dioxolan-4-yl)-acetic acid
  参考文献：
  名称：

  Resolution of a citric acid derivative: synthesis of (R)-(−)-homocitric acid-γ-lactone

  摘要：

  Both the (R) and (S) enantiomers of the citric acid derivative 1 have been obtained in greater than or equal to 90% ee via resolution of the racemate by fractional crystallisation of the (S) and (R)-alpha-methylbenzylamine salts respectively. The stereochemistry of (R)-1 has been assigned by its conversion to (R)-(-)-homocitric acid utilising an Arndt-Eistert homologation followed by acid catalysed deprotection. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00435-7
• 作为产物：
  描述：

  5-氧代-1,3-二氧戊环-4,4-二乙酸 在 N,N-二甲基苯胺 、 三氯氧磷 作用下， 以 氯仿 为溶剂， 反应 0.5h， 以63%的产率得到4,4-(5-oxo-1,3-dioxolane)diacetic acid anhydride
  参考文献：
  名称：

  Total Synthesis of the Siderophore Vibrioferrin.

  摘要：

  通过光学拆分获得的手性二苯基柠檬酸酯，实现了铁载体维里铁素（1）的全合成。研究发现，维里铁素中柠檬酸部分的构型为R型。

  DOI：

  10.1248/cpb.47.459

文献信息

• The design and synthesis of nucleoside triphosphate isosteres as potential inhibitors of HIV reverse transcriptase
  作者：Richard Weaver、Ian H. Gilbert

  DOI：10.1016/s0040-4020(97)00210-x

  日期：1997.4

  describe the synthesis of a variety of lipophilic isosteres of nucleoside triphosphates as potential anti-HIV agents. The citrate molecule proved to be a good mimic of triphosphate by modelling in terms of charge and spatial distribution. Several lipophilc derivatives of citrate were conjugated to the precedented anti-HIV nucleoside d4T via ester and amide linkages. A novel synthesis of 5′-amino-d4T

  我们描述了作为潜在的抗艾滋病毒药物的核苷三磷酸的各种亲脂性等排体的合成。通过在电荷和空间分布方面进行建模，证明柠檬酸盐分子是三磷酸的良好模拟物。几种柠檬酸酯的亲脂性衍生物通过酯和酰胺键与先前的抗HIV核苷d4T缀合。包括5'-氨基-d4T的新合成。还报道了几种酰胺连接的等排物的分子内重排，以及对于所需酰胺连接的等排物的替代合成策略。
• Total Synthesis of the Siderophore Vibrioferrin.
  作者：Yasuo TAKEUCHI、Teruaki AKIYAMA、Takashi HARAYAMA

  DOI：10.1248/cpb.47.459

  日期：——

  Total synthesis of vibrioferrin (1), a siderophore, was achieved via chiral dibenzyl citrate separated by optical resolution. It was elucidated that the configuration of the citrate moiety of vibrioferrin was R.

  通过光学拆分获得的手性二苯基柠檬酸酯，实现了铁载体维里铁素（1）的全合成。研究发现，维里铁素中柠檬酸部分的构型为R型。
• Synthesis and Siderophore Activity of Vibrioferrin and One of Its Diastereomeric Isomers.
  作者：Yasuo TAKEUCHI、Yoshiyuki NAGAO、Kyoko TOMA、Yumiko YOSHIKAWA、Teruaki AKIYAMA、Hiromi NISHIOKA、Hitoshi ABE、Takashi HARAYAMA、Shigeo YAMAMOTO

  DOI：10.1248/cpb.47.1284

  日期：——

  Total synthesis of vibrioferrin (1), a siderophore, was achieved via a chiral dibenzyl citrate obtained by optical resolution. The citrate moity of vibrioferrin was determined to have the R configuration and one of the diastereomeric isomers (1b) of 1 did not exhibit siderophore activity.

  通过光学分辨获得的手性二苄基柠檬酸，成功实现了铁载体维布里费林（1）的全合成。维布里费林的柠檬酸部分被确定为R构型，并且其非对映异构体之一（1b）并未表现出铁载体活性。
• Isosteres of nucleoside triphosphates
  作者：Richard Weaver、Ian H. Gilbert、Naheed Mahmood、Jan Balzarini

  DOI：10.1016/0960-894x(96)00444-1

  日期：1996.10

  This paper describes the design and synthesis of lipophilic isosteres of nucleoside triphosphates as potential inhibitors of HIV reverse transcriptase. The isosteric replacement of the triphosphate group is a modification of the citrate group. Copyright (C) 1996 Elsevier Science Ltd.
• Nau; Brown; Bailey, Journal of the American Chemical Society, 1925, vol. 47, p. 2602
  作者：Nau、Brown、Bailey

  DOI：——

  日期：——