cis-(+/-)-2-phenyl-cyclopropanecarboxylic acid chloride | 62624-90-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: cis-(+/-)-2-phenyl-cyclopropanecarboxylic acid chloride
• 英文别名: Cyclopropanecarbonyl chloride, 2-phenyl-, cis-；(1R,2S)-2-phenylcyclopropane-1-carbonyl chloride
• CAS: 62624-90-2
• 化学式: C₁₀H₉ClO
• 分子量: 180.634
• InChiKey: SODZBMGDYKEZJG-RKDXNWHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  cis-(+/-)-2-phenyl-cyclopropanecarboxylic acid chloride 在 silver orthophosphate 、 palladium diacetate 、 potassium carbonate 、 三乙胺 、 三环己基膦 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 19.0h， 生成 (1R,2R)-1'-methyl-2-phenylspiro[cyclopropane-1,3'-indolin]-2'-one
  参考文献：
  名称：

  Silver-Promoted, Palladium-Catalyzed Direct Arylation of Cyclopropanes: Facile Access to Spiro 3,3′-Cyclopropyl Oxindoles

  摘要：

  The Pd-catalyzed, Ag(I)-mediated intramolecular direct arylation of cyclopropane C H bonds is described. Various spiro 3,3'-cyclopropyl oxindoles can be obtained in good to excellent yields from easily accessible 2-bromoanilides. The kinetic isotope effect was determined and epimerization studies were conducted, suggesting that the formation of a putative Pd-enolate is not operative and that the reaction proceeds via a C-H arylation pathway.

  DOI：

  10.1021/ol4003338
• 作为产物：
  描述：

  顺式-2-苯基环丙烷-1-羧酸 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.25h， 生成 cis-(+/-)-2-phenyl-cyclopropanecarboxylic acid chloride
  参考文献：
  名称：

  [EN] COMPOUNDS AND METHODS FOR TREATING AUTOIMMUNE DISORDERS BY TARGETING HLA-DQ2
  [FR] COMPOSÉS ET MÉTHODES DE TRAITEMENT DE TROUBLES AUTO-IMMUNS PAR CIBLAGE DE HLA-DQ2

  摘要：

  化合物和组合物在通过调节T细胞对由主要组织相容性（MHC）II类分子DQ2呈现的抗原肽或抗原肽片段的反应来治疗、改善或抑制自身免疫疾病的方法中发挥作用。

  公开号：

  WO2022140464A1

文献信息

• [EN] COMPOUNDS AND METHODS FOR TREATING AUTOIMMUNE DISORDERS BY TARGETING HLA-DQ2<br/>[FR] COMPOSÉS ET MÉTHODES DE TRAITEMENT DE TROUBLES AUTO-IMMUNS PAR CIBLAGE DE HLA-DQ2
  申请人：IMMUNOMOLECULAR THERAPEUTICS INC

  公开号：WO2022140464A1

  公开（公告）日：2022-06-30

  Compounds and compositions useful in methods of treating, ameliorating, or inhibiting the development of an autoimmune disease by modulating the T cell response to antigenic peptide or fragments of antigenic peptides presented by the major histocompatibility (MHC) class II molecule, DQ2.

  化合物和组合物在通过调节T细胞对由主要组织相容性（MHC）II类分子DQ2呈现的抗原肽或抗原肽片段的反应来治疗、改善或抑制自身免疫疾病的方法中发挥作用。
• WO2007/27917
  申请人：——

  公开号：——

  公开（公告）日：——
• Selective 5-Hydroxytryptamine 2C Receptor Agonists Derived from the Lead Compound Tranylcypromine: Identification of Drugs with Antidepressant-Like Action
  作者：Sung Jin Cho、Niels H. Jensen、Toru Kurome、Sudhakar Kadari、Michael L. Manzano、Jessica E. Malberg、Barbara Caldarone、Bryan L. Roth、Alan P. Kozikowski

  DOI：10.1021/jm801354e

  日期：2009.4.9

  We report here the design, synthesis, and pharmacological properties of a series of compounds related to tranylcypromine (9), which itself was discovered as a lead compound in a high-throughput screening campaign. Starting from 9, which shows modest activity as a 5-HT2C agonist, a series of 1-aminomethyl-2-phenylcyclopropanes was investigated as 5-HT2C agonists through iterative structural modifications. Key pharmacophore feature of this new class of ligands is a 2-aminomethyl-trans-cyclopropyl side chain attached to a substituted benzene ring. Among the tested compounds, several were potent and efficacious 5-HT2C receptor agonists with selectivity over both 5-HT2A and 5-HT2B receptors in functional assays. The most promising compound is 37, with 120- and 14-fold selectivity over 5-HT2A and 5-HT2B, respectively (EC50 = 585, 65, and 4.8 nM at the 2A, 2B, and 2C subtypes, respectively). In animal studies, compound 37 (10-60 mg/kg) decreased immobility time in the mouse forced swim test.
• WO2007/25144
  申请人：——

  公开号：——

  公开（公告）日：——
• US6162811A
  申请人：——

  公开号：US6162811A

  公开（公告）日：2000-12-19