1-甲酰基环戊烷-1-羧酸甲酯 | 84393-03-3

• 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: 1-甲酰基环戊烷-1-羧酸甲酯
• 英文名称: 1-Formyl-1-methylcyclopentanecarboxylate
• 英文别名: methyl 1-formylcyclopentanecarboxylate；methyl 1-formylcyclopentane-1-carboxylate
• CAS: 84393-03-3
• 化学式: C₈H₁₂O₃
• 分子量: 156.181
• InChiKey: YGQQKLBBWIBWKJ-UHFFFAOYSA-N

物化性质

• 沸点：
  92-93 °C(Press: 17.5 Torr)
• 密度：
  1.189±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  1-甲酰基环戊烷-1-羧酸甲酯 在 4 A molecular sieve 、 硫酸 、 氯化二乙基铝 作用下， 以 二氯甲烷 为溶剂， 反应 29.0h， 生成 1-[(S)-Carbamoyl-((S)-1-phenyl-ethylamino)-methyl]-cyclopentanecarboxylic acid methyl ester
  参考文献：
  名称：

  An Enantioselective Synthesis of Cyclopentyl-L-Aspartic Acid Amenable to Large Scale

  摘要：

  新开发了一种（S）-α氨基-1-（羧基）环戊烷乙酸[（S）-环戊基-L-天冬氨酸]（1）及其N-Boc衍生物2的手性选择性合成方法。该合成方法适用于公斤级制备，避免了低温反应和柱层析。

  DOI：

  10.1055/s-1997-1518
• 作为产物：
  描述：

  环戊酸 在 正丁基锂 、 硫酸 、 二异丁基氢化铝 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 18.0h， 生成 1-甲酰基环戊烷-1-羧酸甲酯
  参考文献：
  名称：

  Tetramethyl 1,1,4,4-cyclohexanetetracarboxylate: preparation and conversion to key precursors of fluorinated, stereochemically defined cyclohexanes

  摘要：

  Stereoselective low-temperature diisobutylaluminum hydride (DIBALH) reduction of the title tetraester 3 affords trans-1,4-dialdehyde 4a as the major product. Fluorination of 4a,b, followed by additional elaboration leads to novel, 1,1,4,4-tetrasubstituted cyclohexanes bearing trans-1,4-difluoromethyl and fluoromethyl groups. The effect of ring size and number of ester substituents on the outcome of the reduction has been examined and treatment of dimethyl 1,1-cycloalkyl diesters 7a-c with excess DIBALH results in reduction of only one ester group. An entry into trans-1,4-trifluoromethylated tetrasubstituted cyclohexanes has been gained through stereoselective SF4 fluorination of 1,1,4,4-cyclohexanetetracarboxylic acid 17. Stereochemical assignments are supported by X-ray crystallographic data.

  DOI：

  10.1021/jo00076a055

文献信息

• Novel α-formylation of α,α-disubstituted esters. Trimethylsilyl trifluoromethanesulphonate-catalysed reaction of ketene silyl acetals with N-t-butylformimidoyl cyanide
  作者：Kohji Okano、Toshiaki Morimoto、Minoru Sekiya

  DOI：10.1039/c39850000119

  日期：——

  General α-formylation of α,α-disubstituted methyl acetates can be achieved by the reaction of ketene silyl acetals (1) with N-t-butylformimidoyl cyanide (2) in the presence of trimethylsilyl trifluoromethanesulphonate (3) as catalyst followed by hydrolysis of the products (4) and/or (5) with copper(II) acetate or hydrogen chloride in aqueous methanol.

  在三甲基甲硅烷基三氟甲磺酸酯（3）存在下，乙烯酮甲硅烷基缩醛（1）与N-叔丁基甲酰亚胺基氰化物（2）反应，可实现α，α-二取代乙酸甲酯的一般α-甲酰化反应。产物（4）和/或（5）与乙酸铜（II）或氯化氢在甲醇水溶液中的混合物。
• Vilsmeier Formylation of<i>O</i>-Silylated Enolates of Carboxylic Esters. A New Method for the Synthesis of α-Formylcarboxylic Esters
  作者：Chaganti P. Reddy、Shigeo Tanimoto

  DOI：10.1055/s-1987-28011

  日期：——

  The Vilsmeier formylation of ketone O-alkyl O′-silyl acetals (O-silylated enolates of carboxylic esters) provides α-formylcarboxylic esters in moderate yields.

  Vilsmeier 甲酰化反应可以将酮 O-烷基 O′-硅烷醚（羧酸酯的 O-硅烷化烯醇盐）转化为 α-甲酰羧酸酯，产率适中。
• Process and intermediates for
  申请人：Boehringer Ingelheim (Canada) Ltd.

  公开号：US05948935A1

  公开（公告）日：1999-09-07

  Disclosed herein is a process for preparing (S)-.alpha.-amino-1-carboxycyclopentaneacetic acid which is a useful intermediate for preparing peptidomimetic inhibitors of herpes viral ribonucleotide reductase. The process comprises the preparation of the key intermediate ##STR1## and its subsequent conversion to the desired product.

  本文披露了一种制备(S)-α-氨基-1-羧基环戊基乙酸的过程，该过程是制备抗疱疹病毒核糖核苷酸还原酶肽类模拟抑制剂的有用中间体。该过程包括制备关键中间体##STR1##及其随后转化为所需产物的步骤。
• Peptide deformylase inhibitors
  申请人：Aubart M. Kelly

  公开号：US20060160802A1

  公开（公告）日：2006-07-20

  Novel PDF inhibitors and novel methods for their use are provided.

  提供了新型PDF抑制剂和其使用的新方法。
• Benzisoxazole Derivatives
  申请人：Noguchi Hirohide

  公开号：US20080207690A1

  公开（公告）日：2008-08-28

  This invention relates to compounds of the formula (I): wherein A, B, R 1 , R 4 , m, and n are each as described herein or a pharmaceutically acceptable salt thereof, and compositions containing such compounds and the use of such compounds in the treatment of a condition mediated by 5-HT 4 receptor activity such as, but not limited to, gastroesophageal reflux disease, gastrointestinal disease, gastric motility disorder, non-ulcer dyspepsia, functional dyspepsia, irritable bowel syndrome (IBS), constipation, dyspepsia, esophagitis, gastroesophageral disease, nausea, central 10 nervous system disease, Alzheimer's disease, cognitive disorder, emesis, migraine, neurological disease, pain, cardiovascular disorders such as cardiac failure and heart arrhythmia, diabetes and apnea syndrome.

  本发明涉及化合物的公式（I）：其中A，B，R1，R4，m和n分别如本文所述或其药学上可接受的盐，并包含这些化合物的组合物以及这些化合物在治疗由5-HT4受体活性介导的疾病中的使用，例如但不限于胃食管反流病，胃肠道疾病，胃动力障碍，非溃疡性消化不良，功能性消化不良，肠易激综合症（IBS），便秘，消化不良，食管炎，胃食管疾病，恶心，中枢神经系统疾病，阿尔茨海默病，认知障碍，呕吐，偏头痛，神经系统疾病，疼痛，心血管疾病，如心力衰竭和心律失常，糖尿病和呼吸暂停综合症。