cis-2,3-epoxysuccinic anhydride

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: cis-2,3-epoxysuccinic anhydride
• 英文别名: (1S,5R)-3,6-dioxabicyclo[3.1.0]hexane-2,4-dione
• 化学式: C₄H₂O₄
• 分子量: 114.057
• InChiKey: ILABOOGTVTXVFN-XIXRPRMCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  55.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  cis-2,3-epoxysuccinic anhydride 在 六甲基二硅氮烷 作用下， 以 乙醚 为溶剂， 反应 96.0h， 以63%的产率得到cis-2,3-epoxysuccinamic acid
  参考文献：
  名称：

  铜蓝蛋白二羧酸类似物的制备

  摘要：

  我们已经提出并合成了一些新的结构型天蓝素类似物，它们具有作为脂肪酸和聚酮化合物合酶多酶复合物抑制剂的潜力。这些类似物含有带有侧翼羧酸盐基团的顺式环氧化物。我们的合成物经过精心设计，可以在四到五个步骤中以收敛的方式从易得的起始原料中获得各种脂肪酸和类似聚酮化合物的侧链。总共已经制备并表征了约40种潜在的类似物，涵盖了所提出的所有结构亚类，其中大多数构成了新颖的功能组。

  DOI：

  10.1002/jhet.5570420511
• 作为产物：
  描述：

  cis-2,3-epoxysuccinic acid 在 三氟乙酸酐 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以100%的产率得到cis-2,3-epoxysuccinic anhydride
  参考文献：
  名称：

  (±) cis-bisamido epoxides: A novel series of potent FXIII-A inhibitors

  摘要：

  A novel class of potent FXIII-A inhibitors containing a (+/-) cis-bisamido epoxide pharmacophore is described. The compounds display highly potent inhibition of FXIII-A (IC50 = 5-500 nM) in an in vitro assay. In contrast to other types of previously described covalent transglutaminase inhibitors, the bis-amido epoxides exhibited no measurable reactivity with glutathione, therefore possibly rendering this class of compounds suitable for future in vivo investigations. Additionally, the compounds show selective inhibition for FXIII-A against the cysteine protease, cathepsin S although they proved to have similar potency with a closely related transglutaminase, TGII, to that observed for FXIII-A. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.05.019

文献信息

• Preparation of dicarboxylate analogues of cerulenin
  作者：Jonathan D. Moseley、James Staunton

  DOI：10.1002/jhet.5570420511

  日期：2005.7

  We have proposed and synthesized several new structural classes of Cerulenin analogues, which have potential as inhibitors of both fatty acid and polyketide synthase multi-enzyme complexes. These analogues contain cis epoxides bearing flanking carboxylate groups. Our syntheses have been designed to allow access to a wide range of fatty acid and polyketide-like side chains from readily available starting

  我们已经提出并合成了一些新的结构型天蓝素类似物，它们具有作为脂肪酸和聚酮化合物合酶多酶复合物抑制剂的潜力。这些类似物含有带有侧翼羧酸盐基团的顺式环氧化物。我们的合成物经过精心设计，可以在四到五个步骤中以收敛的方式从易得的起始原料中获得各种脂肪酸和类似聚酮化合物的侧链。总共已经制备并表征了约40种潜在的类似物，涵盖了所提出的所有结构亚类，其中大多数构成了新颖的功能组。
• Highly diastereoselective desymmetrisation of cyclic meso-anhydrides and derivatisation for use in natural product synthesis
  作者：Amanda C. Evans、Deborah A. Longbottom、Masato Matsuoka、John E. Davies、Richard Turner、Vilius Franckevičius、Steven V. Ley

  DOI：10.1039/b813494d

  日期：——

  A new and efficient desymmetrisation of succinic and glutaric cyclic meso-anhydrides is described, providing excellent yields and diastereoselectivities in most cases. Derivatisation of the desymmetrised products is demonstrated by their conversion into mono-protected 1,4-diols. General synthetic utility of the method is established by its application towards a key fragment in the total synthesis of the immunosuppressant antitumour natural product, rapamycin.

  本文描述了琥珀酸和谷氨酸环状内消旋酐的一种新的高效去对称化方法，在大多数情况下提供了优异的产率和非对映选择性。通过将去对称化产物转化为单保护的1,4-二醇，展示了它们的衍生化能力。通过该方法在免疫抑制抗肿瘤天然产物雷帕霉素的全合成中关键片段的应用，证明了其普遍的合成实用性。
• Highly Diastereoselective Desymmetrisation of Cyclic<i>meso</i>-Anhydrides and Derivatisation to Mono-Protected 1,4-Diols
  作者：Steven V. Ley、Amanda C. Evans、Deborah A. Longbottom、Masato Matsuoka

  DOI：10.1055/s-2005-862393

  日期：——

  providing good yields and diastereo-selectivities in all cases (routinely >95% de). Derivatisation of the chiral compounds synthesised is then demonstrated by their conversion into mono-protected 1,4-diols.

  描述了一种新的、有效的双环和三环内消旋酸酐去对称化，在所有情况下都提供了良好的产率和非对映选择性（通常 >95% de）。然后通过将合成的手性化合物转化为单保护的 1,4-二醇来证明其衍生化。
• (±) cis-bisamido epoxides: A novel series of potent FXIII-A inhibitors
  作者：Craig A. Avery、Richard J. Pease、Kerrie Smith、May Boothby、Helen M. Buckley、Peter J. Grant、Colin W.G. Fishwick

  DOI：10.1016/j.ejmech.2015.05.019

  日期：2015.6

  A novel class of potent FXIII-A inhibitors containing a (+/-) cis-bisamido epoxide pharmacophore is described. The compounds display highly potent inhibition of FXIII-A (IC50 = 5-500 nM) in an in vitro assay. In contrast to other types of previously described covalent transglutaminase inhibitors, the bis-amido epoxides exhibited no measurable reactivity with glutathione, therefore possibly rendering this class of compounds suitable for future in vivo investigations. Additionally, the compounds show selective inhibition for FXIII-A against the cysteine protease, cathepsin S although they proved to have similar potency with a closely related transglutaminase, TGII, to that observed for FXIII-A. (C) 2015 Elsevier Masson SAS. All rights reserved.