4-hydroxy-1-oxaspiro[4.5]dec-3-en-2-one | 16194-41-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: 4-hydroxy-1-oxaspiro[4.5]dec-3-en-2-one
• 英文别名: 4-Hydroxy-1-oxa-spiro[4.5]dec-3-en-2-one
• CAS: 16194-41-5
• 化学式: C₉H₁₂O₃
• mdl: MFCD00463230
• 分子量: 168.192
• InChiKey: LQDMEYONSYGNMJ-UHFFFAOYSA-N

物化性质

• 熔点：
  198 °C
• 沸点：
  353.2±42.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.666
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  m-nitrocinnamyl bromide 、 4-hydroxy-1-oxaspiro[4.5]dec-3-en-2-one 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 丙酮 为溶剂， 反应 0.08h， 以58%的产率得到4-(m-nitrocinnamyloxy)-1-oxaspiro[4.5]dec-3-en-2-one
  参考文献：
  名称：

  Tipranavir analogous 3-sulfonylanilidotetronic acids: new synthesis and structure-dependent anti-HIV activity

  摘要：

  Sulfonamide-containing tetronic acids 1, structural analogues of the HIV-1 protease inhibitor tipranavir, were synthesised in five steps including a microwave-assisted Claisen rearrangement of cinnamyl tetronates and a modified Charette cyclopropanation of the so-formed 3-allyltetronic acids. Compounds 1 with two non-H residues (R-1, R-2) at C-5 of the tetronate core exhibited structure-dependent antiviral activity in two HIV strains. Derivatives 1c (R-1=R-2=Me, R-3=Cl) and 1d (R-1,R-2=(CH2)(5,) R-3=Me) were most active (IC50<10 mu M) in the sensitive strain HIVNL4-3. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.07.094
• 作为产物：
  描述：

  1-cyano-cyclohexyl ethyl malonate 在 盐酸 、 sodium hydroxide 作用下， 反应 74.0h， 生成 4-hydroxy-1-oxaspiro[4.5]dec-3-en-2-one
  参考文献：
  名称：

  Veronese, Augusto C.; Callegari, Rosella; Bertazzo, Antonella, Heterocycles, 1991, vol. 32, # 11, p. 2205 - 2215

  摘要：

  DOI：

文献信息

• CYCLIC KETO-ENOLS FOR THERAPY
  申请人：Liu Ningshu

  公开号：US20130040935A1

  公开（公告）日：2013-02-14

  The invention relates to 5′-biphenyl-substituted cyclic ketoenols for therapeutic purposes, to pharmaceutical compositions and to their use in therapy, in particular for the prophylaxis and therapy of tumour disorders.

  该发明涉及用于治疗目的的5'-联苯取代环状酮醇，药物组合物以及它们在治疗中的使用，特别是用于预防和治疗肿瘤疾病。
• Stereoselective synthesis of biologically active tetronic acids
  作者：Franz Effenberger、Jana Syed

  DOI：10.1016/s0957-4166(98)00040-8

  日期：1998.3

  (4R)-3-Amino-4-trimethylsilyloxy-2-alkenoates (R)-3, obtained from O-trimethylsilyl protected optically active cyanohydrins (R)-1 via the Blaise reaction, are hydrolyzed under mildly acidic conditions to give optically active tetronic acids (R)-4 without racemization. From the follow-up reactions of (R)-4 investigated, only methylation with diazomethane afforded the biologically active tetronic acid derivative (R)-5a without racemization whereas acylation and reductive alkylation, respectively, resulted in partial racemization or failed on the whole. (C) 1998 Elsevier Science Ltd. All rights reserved.

  由O-三甲基硅基保护的光学活性腈酮（R)-1通过Blaise反应得到的(4R)-3-氨基-4-三甲基硅基氧基-2-烯酸酯（R)-3，在温和酸性条件下水解生成无外消旋化的光学活性四氢嘧啶酸（R)-4。对（R)-4的后续反应研究表明，仅甲亚胺的甲基化反应可以得到无外消旋化的生物活性四氢嘧啶酸衍生物（R)-5a，而酰化和还原烷基化分别导致部分外消旋化或完全失败。©1998 Elsevier Science Ltd. 保留所有权利。
• Vinylogous acid derivatives
  申请人：Banner David

  公开号：US20070129421A1

  公开（公告）日：2007-06-07

  The invention is concerned with vinylogous acids derivatives of formula (I) wherein A and R 1 to R 6 are as defined in the description and in the claims, as well as physiologically acceptable salts thereof. These compounds inhibit chymase and can be used as medicaments.

  本发明涉及式(I)的烯丙基酸衍生物，其中A和R1到R6如说明书和权利要求所定义，以及其生理上可接受的盐。这些化合物抑制chymase并可用作药物。
• Insecticidal heterolignans—Tubuline polymerization inhibitors with activity against chewing pests
  作者：Jens Frackenpohl、Isabelle Adelt、Horst Antonicek、Christian Arnold、Patricia Behrmann、Nicole Blaha、Jutta Böhmer、Oliver Gutbrod、Roman Hanke、Sabine Hohmann、Marc van Houtdreve、Peter Lösel、Olga Malsam、Martin Melchers、Valentina Neufert、Elisabeth Peschel、Udo Reckmann、Thomas Schenke、Hans-Peter Thiesen、Robert Velten、Kathrin Vogelsang、Hans-Christoph Weiss

  DOI：10.1016/j.bmc.2009.01.042

  日期：2009.6

  Starting from natural product podophyllotoxin 1 substituted heterolignans were identified with promising insecticidal in vivo activity. The impact of substitution in each segment of the core structure was investigated in a detailed SAR study, and variation of substituents in both aromatic moieties afforded derivatives 5 and 43 with broad insecticidal activity against lepidopteran and coleopteran species. In vitro measurements supported by modeling studies indicate that heterolignans 3-134 act as tubuline polymerization inhibitors interacting with the colchicine-binding site. Insect specific structure-activity effects were observed showing that the insecticidal SAR described herein differs from reported cytotoxicity studies. (C) 2009 Elsevier Ltd. All rights reserved.
• Nomura, Keiichi; Hori, Kozo; Arai, Mikio, Chemical and pharmaceutical bulletin, 1986, vol. 34, # 12, p. 5188 - 5191
  作者：Nomura, Keiichi、Hori, Kozo、Arai, Mikio、Yoshii, Eiichi

  DOI：——

  日期：——