2,3-dimethyl-pentenedioic acid-anhydride | 52101-59-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 2,3-dimethyl-pentenedioic acid-anhydride
• 英文别名: 2,3-Dimethyl-pentendisaeure-anhydrid；4,5-dimethyl-3H-pyran-2,6-dione
• CAS: 52101-59-4
• 化学式: C₇H₈O₃
• 分子量: 140.139
• InChiKey: ONKPOOYIYAFOOK-UHFFFAOYSA-N

物化性质

• 沸点：
  253.9±19.0 °C(Predicted)
• 密度：
  1.170±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,3-dimethyl-pentenedioic acid-anhydride 在 吡啶 、 氢氧化钾 作用下， 以 乙醚 为溶剂， 反应 28.5h， 生成 11-cis,13-cis-12-carbomethoxy-14-methylretinoic acid
  参考文献：
  名称：

  摘要：

  Purpose. Optimization of the therapeutic ratio of analogs of the topically active 11-cis, 13-cis-12-hydroxymethylretinoic acid, delta-lactone (1) relative to antihyperproliferation and antihyperkeratinization vs. toxicity. Methods. Nine analogs of 1, in which variations were made in the lipophilic cyclohexenyl moiety or in the lactone ring, were evaluated for topical activity against hyperkeratinization, inhibition of TPA-induced DNA synthesis and for skin irritation. Results. Although more potent lactones than the parent lactone 1 were identified, none possessed the favorable therapeutic ratio associated with 1. Conclusions. The delta-lactone 1 possesses unique molecular features responsible for its desirable therapeutic ratio as an antihyperproliferative and antihyperkeratotic agent. In view of its very low systemic retinoid toxicity and the absence of any systemic toxicity, this lactone may be a good candidate for use in the topical treatment of acne.

  DOI：

  10.1023/a:1016250129246
• 作为产物：
  描述：

  ethyl α-cyano-β,γ-dimethylglutaconate 在 盐酸 、 三氟乙酸酐 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 生成 2,3-dimethyl-pentenedioic acid-anhydride
  参考文献：
  名称：

  摘要：

  Purpose. Optimization of the therapeutic ratio of analogs of the topically active 11-cis, 13-cis-12-hydroxymethylretinoic acid, delta-lactone (1) relative to antihyperproliferation and antihyperkeratinization vs. toxicity. Methods. Nine analogs of 1, in which variations were made in the lipophilic cyclohexenyl moiety or in the lactone ring, were evaluated for topical activity against hyperkeratinization, inhibition of TPA-induced DNA synthesis and for skin irritation. Results. Although more potent lactones than the parent lactone 1 were identified, none possessed the favorable therapeutic ratio associated with 1. Conclusions. The delta-lactone 1 possesses unique molecular features responsible for its desirable therapeutic ratio as an antihyperproliferative and antihyperkeratotic agent. In view of its very low systemic retinoid toxicity and the absence of any systemic toxicity, this lactone may be a good candidate for use in the topical treatment of acne.

  DOI：

  10.1023/a:1016250129246

文献信息

• Nickelalactone als Synthesebausteine: Sonochemische und Bimetallaktivierung der Kreuzkopplungsreaktion mit Alkyl-halogeniden
  作者：Reinald Fischer、Dirk Walther、Gabriele Braunlich、Bernd Undeutsch、Werner Ludwig、Heinz Bandmann

  DOI：10.1016/0022-328x(92)80077-b

  日期：1992.4

  Nickelalactones with five- and six-membered chelate ring structures can be synthesized in a simple one-pot reaction, starting from Ni(acac)2, bipy, Et3Al and cyclic anhydrides. In the presence of MnI2 and by activation with ultrasound they react selectively with alkyl iodides in cross coupling reactions. The reason for the activating effect of MnI2 is the formation of bimetallic complexes. Many reactive functional groups (e.g. COOR, CHO, CN) can be tolerated. Therefore the cross coupling reaction is of preparative value in the synthesis of functionalized carboxylic acids.
• Notes - 2-Pyrones. XXIV. Derivatives of α,β-Dimethylglutaconic Anhydride
  作者：Richard Wiley、H. Ellert

  DOI：10.1021/jo01354a607

  日期：1957.3
• COMPOUNDS, COMPOSITIONS AND METHODS FOR INHIBITING CNKSR1
  申请人：Phusis Therapeutics, Inc.

  公开号：US20160304533A1

  公开（公告）日：2016-10-20

  Compounds that inhibit CNKSR1, pharmaceutical compositions including compounds that inhibit CNKSR1 and methods of treating disease or disorders that respond to CNKSR1 inhibition are described herein. Additionally, methods of identifying inhibitors of CNKSR1 are described.
• ——
  作者：Anita H. Lewin、Sherry L. Black、Mary E. Bos、R. Richard Goehring、Xina Nair、Gary Whiting、Pamela Bouquin、Geraldine Tetrault、F. Ivy Carroll

  DOI：10.1023/a:1016250129246

  日期：——

  Purpose. Optimization of the therapeutic ratio of analogs of the topically active 11-cis, 13-cis-12-hydroxymethylretinoic acid, delta-lactone (1) relative to antihyperproliferation and antihyperkeratinization vs. toxicity. Methods. Nine analogs of 1, in which variations were made in the lipophilic cyclohexenyl moiety or in the lactone ring, were evaluated for topical activity against hyperkeratinization, inhibition of TPA-induced DNA synthesis and for skin irritation. Results. Although more potent lactones than the parent lactone 1 were identified, none possessed the favorable therapeutic ratio associated with 1. Conclusions. The delta-lactone 1 possesses unique molecular features responsible for its desirable therapeutic ratio as an antihyperproliferative and antihyperkeratotic agent. In view of its very low systemic retinoid toxicity and the absence of any systemic toxicity, this lactone may be a good candidate for use in the topical treatment of acne.