(1R,2S)-2-(hydroxymethyl)cyclopropane-1-carboxylic acid | 206981-98-8

• 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
• 英文名称: (1R,2S)-2-(hydroxymethyl)cyclopropane-1-carboxylic acid
• 英文别名: cis-1-Hydroxymethyl-cyclopropan-carbonsaeure-(2)；cis-2-(hydroxymethyl)cyclopropanecarboxylic acid
• CAS: 206981-98-8
• 化学式: C₅H₈O₃
• 分子量: 116.117
• InChiKey: QAKGVPAQOZSDOZ-QWWZWVQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,2S)-2-(hydroxymethyl)cyclopropane-1-carboxylic acid 在 palladium on activated charcoal pyridinium chlorochromate 、 环己烯 作用下， 以 乙醚 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (1R,2S)-2-(3H-Imidazol-4-yl)-cyclopropanecarboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis and biological evaluation of novel 2-(1H-imidazol-4-yl)cyclopropane carboxylic acids: key intermediates for H3 histamine receptor ligands

  摘要：

  A new synthetic methodology to provide cis-2-(1H-imidazol-4-yl)-cyclopropane carboxylic acids is described. These cyclopropanes are useful for the preparation of novel H-3 receptor agents. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00793-x
• 作为产物：
  描述：

  (3aS,4S,6aR)-4-[[tert-butyl(diphenyl)silyl]oxymethyl]-3,3a,4,6a-tetrahydrofuro[3,4-c]pyrazol-6-one 在 吡啶 、 sodium hydroxide 、 sodium tetrahydroborate 、 二甲基硫 、 四丁基氟化铵 、 臭氧 、 溶剂黄146 、 sodium iodide 、 锌 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 丙酮 、 甲苯 为溶剂， 反应 17.84h， 生成 (1R,2S)-2-(hydroxymethyl)cyclopropane-1-carboxylic acid
  参考文献：
  名称：

  Controlling π-Facial Diastereoselectivity in the 1,3-Dipolar Cycloadditions of Diazomethane to Chiral Pentenoates and Furanones:  Enantioselective Stereodivergent Syntheses of Cyclopropane Hydroxy Acids and Didehydro Amino Acids

  摘要：

  The title compounds have been synthesized in both enantiomeric forms and in good overall yields by using D-glyceraldehyde as the single chiral precursor. The efficiency and usefulness of the synthetic routes have been secured by performing controlled manipulations of the functional groups and by highly stereoselective transformations, namely Wittig-Horner condensations and cyclopropanations. Cyclopropane derivatives have been synthesized through 1,3-dipolar cycloaddition of diazomethane to chiral pentenoates or furanones obtained, in turn, from D-glyceraldehyde. Syn/anti stereochemistry of the cycloadducts has been unequivocally assigned and rationalized. Since pi-facial diastereoselectivity involved in these cycloadditions is the opposite for cyclic and open-chain structures, enantiomeric series of products can be derived.

  DOI：

  10.1021/jo972219a

文献信息

• A Novel, Selective c-Abl Inhibitor, Compound 5, Prevents Neurodegeneration in Parkinson’s Disease
  作者：Seung-Hwan Kwon、Sangjune Kim、A Yeong Park、Saebom Lee、Changdev Gorakshnath Gadhe、Bo Am Seo、Jong-Sung Park、Suyeon Jo、Yumin Oh、Sin Ho Kweon、Shi-Xun Ma、Wonjoong R. Kim、Misoon Kim、Hyeongjun Kim、Jae Eun Kim、Seulki Lee、Jinhwa Lee、Han Seok Ko

  DOI：10.1021/acs.jmedchem.1c01022

  日期：2021.10.28

  Parkinson’s disease (PD) is a progressive neurodegenerative disorder that affects movement. The nonreceptor tyrosine kinase c-Abl has shown a potential role in the progression of PD. As such, c-Abl inhibition is a promising candidate for neuroprotection in PD and α-synucleinopathies. Compound 5 is a newly synthesized blood–brain barrier penetrant c-Abl inhibitor with higher efficacy than existing inhibitors

  帕金森病 (PD) 是一种影响运动的进行性神经退行性疾病。非受体酪氨酸激酶 c-Abl 已显示出在 PD 进展中的潜在作用。因此，c-Abl 抑制是 PD 和 α-突触核蛋白病中神经保护的有希望的候选者。Compound 5 是一种新合成的血脑屏障渗透性 c-Abl 抑制剂，其疗效高于现有抑制剂。当前研究的目的是证明化合物 5 对 PD 的 α-突触核蛋白预形成原纤维 (α-syn PFF) 小鼠模型的神经保护作用。化合物 5 显着降低了皮质神经元中由 α-syn PFF 引起的神经毒性、c-Abl 的激活和路易体病理。此外，化合物 5 显着改善了多巴胺能神经元的丧失、c-Abl 激活、路易体病理、神经炎症反应、体内。综上所述，这些结果表明化合物 5 可能是预防 PD 和 α-突触核蛋白病进展的药剂。
• Synthesis and biological evaluation of novel 2-(1H-imidazol-4-yl)cyclopropane carboxylic acids: key intermediates for H3 histamine receptor ligands
  作者：Miguel F Braña、Cristina Guisado、Luis Fernando Alguacil、Elisa Garrido、Carmen Pérez-Garcı́a、Mariano Ruiz-Gayo

  DOI：10.1016/s0960-894x(02)00793-x

  日期：2002.12

  A new synthetic methodology to provide cis-2-(1H-imidazol-4-yl)-cyclopropane carboxylic acids is described. These cyclopropanes are useful for the preparation of novel H-3 receptor agents. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Controlling π-Facial Diastereoselectivity in the 1,3-Dipolar Cycloadditions of Diazomethane to Chiral Pentenoates and Furanones:  Enantioselective Stereodivergent Syntheses of Cyclopropane Hydroxy Acids and Didehydro Amino Acids
  作者：Marta Martín-Vilà、Neuh Hanafi、José M. Jiménez、Angel Alvarez-Larena、Joan F. Piniella、Vicenç Branchadell、Antonio Oliva、Rosa M. Ortuño

  DOI：10.1021/jo972219a

  日期：1998.5.1

  The title compounds have been synthesized in both enantiomeric forms and in good overall yields by using D-glyceraldehyde as the single chiral precursor. The efficiency and usefulness of the synthetic routes have been secured by performing controlled manipulations of the functional groups and by highly stereoselective transformations, namely Wittig-Horner condensations and cyclopropanations. Cyclopropane derivatives have been synthesized through 1,3-dipolar cycloaddition of diazomethane to chiral pentenoates or furanones obtained, in turn, from D-glyceraldehyde. Syn/anti stereochemistry of the cycloadducts has been unequivocally assigned and rationalized. Since pi-facial diastereoselectivity involved in these cycloadditions is the opposite for cyclic and open-chain structures, enantiomeric series of products can be derived.