2-甲基环丙烷羧酸甲酯 | 71441-77-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 2-甲基环丙烷羧酸甲酯
• 英文名称: Methyl 2-methylcyclopropanecarboxylate
• 英文别名: ethyl 2-methylcyclopropanecarboxylate；2-Methyl-cyclopropan-carbonsaeure-(1)-methylester；2-Methyl-cyclopropancarbonsaeure-methylester；1-Methyl-2-methoxycarbonyl-cyclopropan；2-Methyl-1-methoxycarbonyl-cyclopropan；Methyl 2-methylcyclopropane-1-carboxylate
• CAS: 71441-77-5
• 化学式: C₆H₁₀O₂
• mdl: MFCD12024933
• 分子量: 114.144
• InChiKey: KHHQNCNOFKTABM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.833
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-甲基环丙烷羧酸甲酯 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 0.5h， 以0.72 g的产率得到2-甲基环丙甲醇
  参考文献：
  名称：

  二嗪嗪的热分解：3-（3-甲基二氮杂-3-基）丙-1-醇和3-（3-甲基二氮杂-3-基）丙酸

  摘要：

  在溶液温度范围为96–60℃的条件下，研究了3-（3-甲基二氮杂-3-基）丙-1-醇（1）和3-（3-甲基二氮杂-3-基）丙酸（2）的热解反应。 125℃。反应是单分子的，并且拟合线性Arrhenius图，其中K（1）= 10 13.85±0.69 exp [–31.80±1.21 kcal mol –1 / RT ] s –1和K（2）= 10 12.38±0.43 exp [–29.26± 0.75 kcal mol –1 / RT ] s –1

  DOI：

  10.1039/p29900000661
• 作为产物：
  描述：

  4-氯戊酸甲酯 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 2-甲基环丙烷羧酸甲酯
  参考文献：
  名称：

  Process for cyclizing upsilon-chlorocarboxylic acids

  摘要：

  使用甲醇或乙醇的钠或钾醇盐，在同一种醇的存在下，在高于所使用醇的沸点的温度下，将.gamma.-氯羧酸甲酯或乙酯环化为相应的环丙烷羧酸酯。

  公开号：

  US04520209A1

文献信息

• [EN] PYRIMIDINE COMPOUNDS AS TUBERCULOSIS INHIBITORS<br/>[FR] COMPOSÉS PYRIMIDINE EN TANT QU'INHIBITEURS DE LA TUBERCULOSE
  申请人：VERTEX PHARMA

  公开号：WO2011019405A1

  公开（公告）日：2011-02-17

  The present invention relates to compounds II useful as inhibitors of treating tuberculosis. The invention also provides processes for preparing compounds of the invention.

  本发明涉及化合物II，用作治疗结核病的抑制剂。该发明还提供了制备本发明化合物的方法。
• Interactive design and synthesis of a novel antibacterial agent
  作者：Saul Wolfe、Haolun Jin、Kiyull Yang、Chan-Kyung Kim、Ernest McEachern

  DOI：10.1139/v94-133

  日期：1994.4.1

  β-Lactam compounds act on penicillin-recognizing enzymes via acylation of the hydroxyl group of an active site serine. When the resulting acyl enzyme is kinetically stable, as in the case of a penicillin-binding protein (PBP), the biosynthesis of a bacterial cell wall is inhibited, and death of the organism results. The de novo design of an antibacterial agent targeted to a PBP might be possible if the three-dimensional structural requirements of the equilibrium (i.e, fit) and catalytic (i.e. reactivity) steps of the aforementioned enzymatic process could be determined. For a model of the active site of a PBP from Streptomyces R61, the use of molecular mechanics calculations to treat "fit," and ab initio molecular orbital calculations to treat "reactivity," leads to the idea that the carboxyl group (G₁) and the amide N-H (G₂) of the antibiotic are hydrogen bonded to a lysine amino group and a valine carbonyl group in the enzyme–substrate complex. These two hydrogen bonds place the serine hydroxyl group on the convex face of the antibiotic, in position for attack on the β-lactam ring by a neutral reaction, catalyzed by water, that involves a direct proton transfer to the β-lactam nitrogen. Molecular orbital calculations of structure–reactivity relations associated with this mechanism suggest that C=N is bioisosteric to the β-lactam N-C(=O), comparable to a β-lactam in its reactivity with an alcohol, and that the product RO(C-N)H is formed essentially irreversibly (−ΔE > 10 kcal/mol). Accordingly, structures containing a G₁ and a G₂ separated by a C=N, and positioned in different ways with respect to this functional group, have been synthesized computationally and examined for their ability to fit to the PBP model. This strategy identified a 2H-5,6-dihydro-1,4-thiazine substituted by hydroxyl and carboxyl groups as a target for chemical synthesis. However, exploratory experiments suggested that the C=N of this compound equilibrates with endocyclic and exocyclic enamine tautomers. This required that the C2 position be substituted, and that the hydroxyl group not be attached to the carbon atom adjacent to the C=N. These conditions are met in a 2,2-dimethyl-3-(2-hydroxypropyl)-1,4-thiazine, which also exhibits the necessary fit to the PBP model. Two epimers of this compound have been synthesized, from D- and L-serine. The compound derived from L-serine is not active. The compound derived from D-serine exhibits antibacterial activity, but is unstable, and binding studies with PBP's have not been performed. It is hoped that these studies can be carried out if modification of the lead structure leads to compounds with improved chemical stability.

  β-内酰胺化合物通过酰化活性位点丝氨酸的羟基作用于青霉素识别酶。当产生的酰酶在动力学上是稳定的，如青霉素结合蛋白（PBP）的情况下，细菌细胞壁的生物合成被抑制，导致生物体的死亡。如果能确定青霉素结合蛋白的三维结构要求（即平衡的适合性）和催化（即反应性）步骤的需求，可能会实现针对PBP的抗菌剂的全新设计。对来自链霉菌R61的PBP的活性位点模型，使用分子力学计算处理“适合性”，并使用从头算分子轨道计算处理“反应性”，得出一个想法，即抗生素的羧基（G1）和酰胺N-H（G2）与酶-底物复合物中的赖氨酸氨基团和缬氨酸羰基团形成氢键。这两个氢键将丝氨酸羟基置于抗生素的凸面上，处于通过中性反应由水催化的直接质子转移至β-内酰胺氮原子的位置。与这种机制相关的结构-反应关系的分子轨道计算表明，C=N与β-内酰胺N-C(=O)是生物等同物，与醇类反应时与β-内酰胺相当，产物RO(C-N)H基本上是不可逆的（−ΔE > 10 kcal/mol）。因此，含有由C=N分隔的G1和G2的结构，并以不同方式相对于这个功能团定位的结构已经通过计算合成并检验其适合于PBP模型的能力。这种策略确定了一个被羟基和羧基取代的2H-5,6-二氢-1,4-噻嗪作为化学合成的目标。然而，探索性实验表明，该化合物的C=N与内环和外环烯胺互变异构体平衡。这要求对C2位置进行取代，并且羟基不能连接到邻近C=N的碳原子。这些条件在2,2-二甲基-3-(2-羟基丙基)-1,4-噻嗪中得到满足，该化合物还展现出与PBP模型的必要适合性。这种化合物的两个对映体已经从D-丝氨酸和L-丝氨酸合成。从L-丝氨酸衍生的化合物不活跃。从D-丝氨酸衍生的化合物表现出抗菌活性，但不稳定，并且尚未进行与PBP的结合研究。希望如果引物结构的修改导致具有改善化学稳定性的化合物，这些研究可以进行。
• CYCLOPROPYLBORONIC COMPOUNDS, METHOD FOR PREPARING SAME AND USE THEREOF
  申请人：DIVERCHIM

  公开号：US20150329566A1

  公开（公告）日：2015-11-19

  Cyclopropylboronic compounds, the preparation process thereof and the use thereof.

  环丙基硼化合物，其制备方法及用途。
• [EN] NEW COMPOUNDS FOR THE TREATMENT OF CNS DISORDERS<br/>[FR] NOUVEAUX COMPOSÉS POUR LE TRAITEMENT DE TROUBLES DU SNC
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2011018495A1

  公开（公告）日：2011-02-17

  The invention relates to novel pyrazolopyrimidinones according to formula (I). The new compounds shall be used for the manufacture of medicaments, in particular medicaments for the treatment of conditions concerning deficits in perception, concentration, learning or memory. The new compounds are also for the manufacture of medicaments for the treatment of Alzheimer's disease. Further aspects of the present invention refer to a process for the manufacture of the compounds and their use for producing medicaments.

  该发明涉及根据式(I)的新型吡唑吡嘧啶酮。新化合物应用于制造药物，特别是用于治疗感知、注意力、学习或记忆缺陷相关疾病的药物。新化合物还用于制造治疗阿尔茨海默病的药物。本发明的进一步方面涉及制造这些化合物的方法以及它们用于制造药物的用途。
• NEW COMPOUNDS FOR THE TREATMENT OF CNS DISORDER
  申请人：HEINE Niklas

  公开号：US20110212960A1

  公开（公告）日：2011-09-01

  The invention relates to novel pyrazolopyrimidinones according to formula (I). The new compounds shall be used for the manufacture of medicaments, in particular medicaments for the treatment of conditions concerning deficits in perception, concentration, learning or memory. The new compounds are also for the manufacture of medicaments for the treatment of Alzheimer's disease. Further aspects of the present invention refer to a process for the manufacture of the compounds and their use for producing medicaments.

  该发明涉及根据式(I)的新型吡唑吡嘧啶酮。这些新化合物将用于制造药物，特别是用于治疗涉及感知、注意力、学习或记忆缺陷的药物。这些新化合物还将用于制造治疗阿尔茨海默病的药物。本发明的进一步方面涉及制造这些化合物的过程以及它们用于生产药物的用途。