(-)-(4S,5S)-2,2-dimethyl-[1,3]-dioxolane-4,5-dicarbonitrile | 119209-15-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (-)-(4S,5S)-2,2-dimethyl-[1,3]-dioxolane-4,5-dicarbonitrile
• 英文别名: (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dicarbonitrile；(4R,5R)-2,2-dimethyl-4,5-dicyano-1,3-dioxolane；2,2-dimethyl-4,5-dicyano-1,3-dioxolane；2,3-O-isopropylidene-L-tartaronitrile；(4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-dicarbonitrile
• CAS: 119209-15-3
• 化学式: C₇H₈N₂O₂
• 分子量: 152.153
• InChiKey: IEVTXPMHWLBUQT-WDSKDSINSA-N

物化性质

• 熔点：
  155-157 °C
• 沸点：
  319.9±42.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  66
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (-)-(4S,5S)-2,2-dimethyl-[1,3]-dioxolane-4,5-dicarbonitrile 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 4.0h， 以26%的产率得到(4S,5S)-4,5-二(氨甲基)-2,2-二甲基二氧杂烷
  参考文献：
  名称：

  Analogs of cisplatin derived from diaminodideoxytetritols. Synthesis and activity against the ADJ/PC6 plasmacytoma in mice

  摘要：

  Four new analogues of the anticancer drug cisplatin have been prepared that contain a diaminodideoxytetritol derivative as the amine ligand moiety, and their activities have been measured against the ADJ/PC6 plasmacytoma in mice. Two of these compounds, the enantiomers of cis-dichloro(1,4-diamino-1,4-dideoxy-2,3-O-isopropylidenethreitol) -platinum(II) , show a higher TI value than cisplatin when administered by intraperitoneal injection and, importantly, show significant antitumour activity when administered orally.

  DOI：

  10.1021/jm00124a004
• 作为产物：
  描述：

  (-)-二甲基-2,3-邻异丙亚基-L-酒石酸酯 在 ammonium hydroxide 、 苯磺酰氯 作用下， 以 吡啶 为溶剂， 反应 73.0h， 生成 (-)-(4S,5S)-2,2-dimethyl-[1,3]-dioxolane-4,5-dicarbonitrile
  参考文献：
  名称：

  由（2 R，3 R）-酒石酸合成4-羟基-2,5-二甲基呋喃-3（2 H）-一（呋喃醇）

  摘要：

  （2R，3R）-酒石酸（6）已通过五步转换成重要的挥发性风味和香气成分4-羟基-2,5-二甲基呋喃-3（2 H）-一（呋喃酚）（1），总收率为18.5％。关键步骤涉及通过氯化甲基镁与相应的4,5-双（二甲基酰胺）的反应形成（4 R，5 R）-4,5-二乙酰基-2,2-二甲基-1,3-二氧戊环（10） ）。还通过涉及在相应的二腈上的格氏（Grignard）型反应的相关反应序列，也制备了相同的二氧戊环（10）。

  DOI：

  10.1039/p19850000795

文献信息

• Facile and Racemization-Free Conversion of Chiral Nitriles into Pyridine Derivatives
  作者：Barbara Heller、Bernd Sundermann、Christine Fischer、Jingsong You、Waiqiang Chen、Hans-Joachim Drexler、Paul Knochel、Werner Bonrath、Andrey Gutnov

  DOI：10.1021/jo030206t

  日期：2003.11.1

  The results described herein demonstrate how the very mild reaction conditions of the Co(I)-catalyzed photochemical [2 + 2 + 2] cyclocotrimerization are suited to prepare chiral compounds containing unsubstituted and polysubstituted 2-pyridyl moieties starting from chiral nitriles without any detectable loss of enantiomerical purity. This further increases the already very broad synthetic scope of

  本文所述的结果证明了Co（I）催化的光化学[2 + 2 + 2]环共三聚反应的温和反应条件如何适合于从手性腈开始制备包含未取代和多取代的2-吡啶基部分的手性化合物，而没有任何可检测到的损失对映体纯度。这进一步增加了该特定反应已经非常广泛的合成范围。
• Design, Synthesis, and Biological Evaluation of Novel Hybrid Dicaffeoyltartaric/Diketo Acid and Tetrazole-Substituted <scp>l</scp>-Chicoric Acid Analogue Inhibitors of Human Immunodeficiency Virus Type 1 Integrase
  作者：David C. Crosby、Xiangyang Lei、Charles G. Gibbs、Brenda R. McDougall、W. Edward Robinson、Manfred G. Reinecke

  DOI：10.1021/jm1010594

  日期：2010.11.25

  Fourteen analogues of the anti-HIV-1 integrase (IN) inhibitor L-chicoric acid (L-CA) were prepared. Their IC50 values for 3'-end processing and strand transfer against recombinant HIV-1 IN were determined in vitro, and their cell toxicities and EC50 against HIV-1 were measured in cells (ex vivo). Compounds 1-6 are catechol/beta-diketoacid hybrids, the majority of which exhibit submicromolar potency against 3'-end processing and strand transfer, though only with modest antiviral activities. Compounds 7-10 are L-CA/p-fluorobenzylpyrroloyl hybrids, several of which were more potent against strand transfer than 3'-end processing, a phenomenon previously attributed to the beta-diketo acid pharmacophore. Compounds 11-14 are tetrazole bioisosteres of L-CA and its analogues, whose in vitro potencies were comparable to L-CA but with enhanced antiviral potency. The trihydroxyphenyl analogue 14 was 30-fold more potent than L-CA at relatively nontoxic concentrations. These data indicate that L-CA analogues are attractive candidates for development into clinically relevant inhibitors of HIV-1 IN.
• Chelucci, Giorgio; Falorni, Massimo; Giacomelli, Giampaolo, Gazzetta Chimica Italiana, 1990, vol. 120, p. 731 - 732
  作者：Chelucci, Giorgio、Falorni, Massimo、Giacomelli, Giampaolo

  DOI：——

  日期：——
• HAINES, ALAN H.;MORLEY, CHRISTOPHER;MURRER, BARRY A., J. MED. CHEM., 32,(1989) N, C. 742-745
  作者：HAINES, ALAN H.、MORLEY, CHRISTOPHER、MURRER, BARRY A.

  DOI：——

  日期：——
• CHELUCCI, GIORGIO;FALORNI, MASSIMO;GIACOMELLI, GIAMPAOLO, GAZZ. CHIM. ITAL., 120,(1990) N2, C. 731-732
  作者：CHELUCCI, GIORGIO、FALORNI, MASSIMO、GIACOMELLI, GIAMPAOLO

  DOI：——

  日期：——