Methyl 1,4-dioxa-7-thiaspiro[4.4]nonane-9-carboxylate | 121023-57-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Methyl 1,4-dioxa-7-thiaspiro[4.4]nonane-9-carboxylate
• CAS: 121023-57-2
• 化学式: C₈H₁₂O₄S
• 分子量: 204.247
• InChiKey: PHZMKLAUAQWOQJ-UHFFFAOYSA-N

物化性质

• 沸点：
  296.6±40.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  70.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Methyl 1,4-dioxa-7-thiaspiro[4.4]nonane-9-carboxylate 在 二异丁基氢化铝 作用下， 以 二氯甲烷 为溶剂， 以70%的产率得到1,4-Dioxa-7-thia-spiro[4.4]nonane-9-carbaldehyde
  参考文献：
  名称：

  一种有效的2,3-二亚甲基吡咯方法。吡咯并3-磺基烯烃的制备和反应

  摘要：

  已开发出一条新的路线以制备吡咯并-3-硫杂环丁烷，该路线可用于产生相应的2,3-二亚甲基吡咯，并且已经成功地进行了它们的环加成和取代反应。

  DOI：

  10.1039/c39920000549
• 作为产物：
  描述：

  4-氧四氢噻酚-3-羧酸甲酯 、 乙二醇 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 生成 Methyl 1,4-dioxa-7-thiaspiro[4.4]nonane-9-carboxylate
  参考文献：
  名称：

  Design of Inhibitors of Scytalone Dehydratase: Probing Interactions with an Asparagine Carboxamide

  摘要：

  Among the active-site residues of scytalone dehydratase, the side-chain carboxamide of asparagine 131 has the greatest potential for strong electrostatic interactions. Structure-based inhibitor design aimed at enhancing interactions with this residue led to the synthesis of a series of highly potent inhibitors that have a five- or six-membered ring containing a carbonyl functionality for hydrogen bonding. To achieve a good orientation for hydrogen bonding, the inhibitors incorporate a phenyl substituent that displaces a phenylalanine residue away from the five- or six-membered rings. Without the phenyl substituent, inhibitor binding potency is diminished by three orders of magnitude. Larger K, values of a site-directed mutant (Asn131Ala) of scytalone dehydratase in comparison to those of wild-type enzyme validate the design concept. The most potent inhibitor (K-i = 15 pM) contains a tetrahydrothiophenone that can form a single hydrogen bond with the asparagine carboxamide. Inhibitors with a butyrolactam that can form two hydrogen bonds with the asparagine carboxamide demonstrate excellent in vivo fungicidal activity. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00272-9

文献信息

• An efficient approach toward 2,3-dimethylene pyrroles. Preparation and reactions of pyrrolo-3-sulfolenes
  作者：Ta-Shue Chou、Ruei-Chih Chang

  DOI：10.1039/c39920000549

  日期：——

  A new route has been developed toward the preparation of pyrrolo-3-sulfolenes, which can be used to generate the corresponding 2,3-dimethylene pyrroles, and their cycloaddition and substitution reactions have been successfully performed.

  已开发出一条新的路线以制备吡咯并-3-硫杂环丁烷，该路线可用于产生相应的2,3-二亚甲基吡咯，并且已经成功地进行了它们的环加成和取代反应。
• Design of Inhibitors of Scytalone Dehydratase: Probing Interactions with an Asparagine Carboxamide
  作者：Gregory S Basarab、Douglas B Jordan、Troy C Gehret、Rand S Schwartz

  DOI：10.1016/s0968-0896(02)00272-9

  日期：2002.12

  Among the active-site residues of scytalone dehydratase, the side-chain carboxamide of asparagine 131 has the greatest potential for strong electrostatic interactions. Structure-based inhibitor design aimed at enhancing interactions with this residue led to the synthesis of a series of highly potent inhibitors that have a five- or six-membered ring containing a carbonyl functionality for hydrogen bonding. To achieve a good orientation for hydrogen bonding, the inhibitors incorporate a phenyl substituent that displaces a phenylalanine residue away from the five- or six-membered rings. Without the phenyl substituent, inhibitor binding potency is diminished by three orders of magnitude. Larger K, values of a site-directed mutant (Asn131Ala) of scytalone dehydratase in comparison to those of wild-type enzyme validate the design concept. The most potent inhibitor (K-i = 15 pM) contains a tetrahydrothiophenone that can form a single hydrogen bond with the asparagine carboxamide. Inhibitors with a butyrolactam that can form two hydrogen bonds with the asparagine carboxamide demonstrate excellent in vivo fungicidal activity. (C) 2002 Elsevier Science Ltd. All rights reserved.