3-Isopropoxy-4-isopropyl-3-cyclobutene-1,2-dione | 73279-65-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-Isopropoxy-4-isopropyl-3-cyclobutene-1,2-dione
• 英文别名: 3-Cyclobutene-1,2-dione, 3-(1-methylethoxy)-4-(1-methylethyl)-；3-propan-2-yl-4-propan-2-yloxycyclobut-3-ene-1,2-dione
• CAS: 73279-65-9
• 化学式: C₁₀H₁₄O₃
• 分子量: 182.219
• InChiKey: FBLBQHVIARGWAP-UHFFFAOYSA-N

物化性质

• 沸点：
  270.5±50.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  3-Isopropoxy-4-isopropyl-3-cyclobutene-1,2-dione 在 盐酸 作用下， 以 丙酮 、 苯 为溶剂， 生成 3-isopropyl-4-methoxycyclobut-3-ene-1,2-dione
  参考文献：
  名称：

  A synthesis of the abietane diterpenoid quinone (±)-royleanone via maleoylcobalt technology.

  摘要：

  DOI：

  10.1016/s0040-4039(00)97454-9
• 作为产物：
  描述：

  4-Hydroxy-2,3-diisopropoxy-4-isopropyl-2-cyclobuten-1-on 在 盐酸 作用下， 以 乙醚 为溶剂， 反应 2.0h， 以57%的产率得到3-Isopropoxy-4-isopropyl-3-cyclobutene-1,2-dione
  参考文献：
  名称：

  Dehmlow, Eckehard V.; Schell, Hans G., Chemische Berichte, 1980, vol. 113, # 1, p. 1 - 8

  摘要：

  DOI：

文献信息

• Nickel-catalyzed ring-opening of α-hydroxycyclobutenones with a remarkable ligand effect
  作者：Songsong Gao、Xiangdong Hu

  DOI：10.1039/c7cc03340k

  日期：——

  A Ni-catalyzed ring-opening of α-hydroxycyclobutenones is reported herein. A remarkable ligand effect was observed during transformations following the ring-opening. The employment of PPh3 leads to the formation of 2-furanones 2 through a migration of an alkoxyl group, and 2-furanones 3 were generated through a migration of hydrogen in the presence of Xantphos, affording a divergent approach to 2-furanones

  本文报道了Ni催化的α-羟基环丁烯酮的开环。开环后的转化过程中观察到了显着的配体效应。PPh3的使用通过烷氧基的迁移导致形成2-呋喃酮2，而在Xantphos的存在下通过氢的迁移生成了2-呋喃酮3，从而提供了一种具有多种功能的2-呋喃酮的发散方法。组。
• RAS INHIBITORS AND USES THEREOF
  申请人：DANA-FARBER CANCER INSTITUTE, INC.

  公开号：US20160046661A1

  公开（公告）日：2016-02-18

  Described herein are compounds of Formulae (I)-(II), and pharmaceutically acceptable salts, and pharmaceutical compositions thereof. Also provided are methods and kits involving the inventive compounds or compositions for treating or preventing proliferative diseases such as cancers (e.g., lung cancer, large bowel cancer, pancreas cancer, biliary tract cancer, or endometrial cancer), benign neoplasms, angiogenesis, inflammatory diseases, autoinflammatory diseases, and autoimmune diseases in a subject.

  本文描述了式（I）-（II）的化合物，以及其药学上可接受的盐和制药组合物。还提供了涉及创新化合物或组合物的方法和工具包，用于治疗或预防受试者的增殖性疾病，如癌症（例如肺癌，大肠癌，胰腺癌，胆道癌或子宫内膜癌），良性肿瘤，血管生成，炎症性疾病，自身炎症性疾病和自身免疫性疾病。
• A strategy for generalization of the regiospecific synthesis of substituted quinones from cyclobutenediones
  作者：Lanny S. Liebeskind、Kenneth L. Granberg、Jing Zhang

  DOI：10.1021/jo00042a009

  日期：1992.7

  Documented within is a straightforward protocol for the synthesis of generally substituted benzoquinones and ring-fused quinones. Previously, the crucial issue of quinone substituent regiochemistry was resolved at the stage of addition of an unsaturated carbon nucleophile to a cyclobutenedione by using either symmetrically substituted cyclobutenediones or 3-alkoxy (or amino)-4-substituted-3-cyclobutenediones. In the former case there are no regioisomeric quinones formed, while in the latter, through resonance delocalization, the alkoxy (or amino) substituent renders one of the two carbonyl groups less reactive and directs the incoming nucleophile to the other. The placement of a wide variety of substituents about the quinone ring periphery has now been solved by the less restrictive strategy of sequential introduction of substituents onto a cyclobutenedione core. The chemistry commences with 3-isopropoxy-4-substituted-3-cyclobutene-1,2-diones. Addition of an aromatic, heteroaromatic, or alkenyl nucleophile to the more reactive carbonyl group provides 4-hydroxy-4-R(unsat)-2-cyclobutenones, which are protected as the methyl ethers by treatment with MeI/Ag2O/K2CO3 in MeCN. A second nucleophile is added, again in a 1,2-sense, providing highly substituted 3-isopropoxy-2-cyclobutenols that are arranged to cyclobutenones under acidic conditions. The resulting cyclobutenones are converted into substituted quinones by thermolysis at 140-degrees-C in o-xylene followed by oxidative workup with ceric ammonium nitrate. The substitution pattern about the quinone core is rigorously controlled by the sequence of introduction of the substituents.
• Inhibitors of Thermus thermophilus Isopropylmalate Dehydrogenase
  作者：Michael C. Pirrung、Hyunsoo Han、Richard T. Ludwig

  DOI：10.1021/jo00088a026

  日期：1994.5

  In an attempt to use mechanism-based design for the discovery of inhibitors of the isopropylmalate dehydrogenase from T. thermophilus, we have prepared and studied a number of potential mimics for an intermediate in the oxidative decarboxylation of isopropyl malate, the enol or enolate of alpha-ketoisocaproate. Because hydroxamate and dicarboxylate enolate mimics are strong, uncompetitive inhibitors of the enzyme and vinyl fluoride enol mimics are weak, competitive inhibitors, it is suggested that the reaction involves the enolate. The uncompetitive inhibition by a number of anionic compounds suggests, in combination with previous studies in other laboratories, that they mimic the enolate product of the decarboxylation. An explanation for the potency of the inhibition of IMDH by these compounds is proposed based on the electrostatic interaction of product and cofactor.
• Dehmlow, Eckehard V.; Neuhaus, Rainer; Schell, Hans G., Chemische Berichte, 1988, vol. 121, p. 569 - 572
  作者：Dehmlow, Eckehard V.、Neuhaus, Rainer、Schell, Hans G.

  DOI：——

  日期：——