2-methoxycarbonyl-2-tetrahydrofuroic acid | 327618-73-5

• 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
• 英文名称: 2-methoxycarbonyl-2-tetrahydrofuroic acid
• 英文别名: 2-Methoxycarbonyloxolane-2-carboxylic acid
• CAS: 327618-73-5
• 化学式: C₇H₁₀O₅
• 分子量: 174.153
• InChiKey: PKCSCZWLOIOQHR-UHFFFAOYSA-N

物化性质

• 沸点：
  295.4±40.0 °C(Predicted)
• 密度：
  1.359±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-methoxycarbonyl-2-tetrahydrofuroic acid 在 sodium hydroxide 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 (S)-3-(2'-Methoxy-biphenyl-4-yl)-2-{[(S)-2-(pyrrolidine-1-carbonyl)-tetrahydro-furan-2-carbonyl]-amino}-propionic acid
  参考文献：
  名称：

  Substituted tetrahydrofuroyl-1-phenylalanine derivatives as potent and specific VLA-4 antagonists

  摘要：

  A series of substituted tetra hydrofuroyl-1-phenylalanine derivatives was prepared and evaluated as VLA-4 antagonists. Substitution of the a carbon of the tetrahydrofuran with aryl groups increased the specificity for VLA-4 versus alpha(4)beta(7) while amide substitution increased the potency of the series without increasing the specificity. Substitution of the P carbon of the tetrahydrofuran with keto or amino groups slightly improved the specificity for VLA-4 versus alpha(4)beta(7) but with a significant loss in binding affinity for VLA-4. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00211-1
• 作为产物：
  描述：

  2-四氢呋喃甲酸 在 氯化亚砜 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 生成 2-methoxycarbonyl-2-tetrahydrofuroic acid
  参考文献：
  名称：

  Asymmetric Protonation of Lithium Enolate of α-Amino Acid Derivatives using Chiral Brønsted Acids

  摘要：

  具有不对称2-噁唑烷环的手性醇被合成作为新的手性布朗斯特酸，原料为四氢-2-呋喃酸和(1S,2R)-2-氨基-1,2-二苯乙醇。这些醇在作为手性质子源方面优于之前报道的(S,S)-或(R,R)-酰亚胺，能够用于氨基酸衍生物锂烯醇盐的对映选择性质子化反应。

  DOI：

  10.1055/s-2001-18754

文献信息

• Heterocycle amides as cell adhesion inhibitors
  申请人：Merck & Co., Inc.

  公开号：US06420418B1

  公开（公告）日：2002-07-16

  Compounds of Formula I are antagonists of VLA-4 and/or &agr;4&bgr;7, and as such are useful in the inhibition or prevention of cell adhesion and cell-adhesion mediated pathologies. These compounds may be formulated into pharmaceutical compositions and are suitable for use in the treatment of AIDS-related dementia, allergic conjunctivitis, allergic rhinitis, Alzheimer's disease, asthma, atherosclerosis, autologous bone marrow transplantation, certain types of toxic and immune-based nephritis, contact dermal hypersensitivity, inflammatory bowel disease including ulcerative colitis and Crohn's disease, inflammatory lung diseases, inflammatory sequelae of viral infections, meningitis, multiple sclerosis, multiple myeloma, myocarditis, organ transplantation, psoriasis, pulmonary fibrosis, restenosis, retinitis, rheumatoid arthritis, septic arthritis, stroke, tumor metastasis, uveititis, and type I diabetes.

  公式I的化合物是VLA-4和/或α4β7的拮抗剂，因此可用于抑制或预防细胞粘附和细胞粘附介导的病理。这些化合物可配制成药物组合物，适用于治疗与艾滋病相关的痴呆、过敏性结膜炎、过敏性鼻炎、阿尔茨海默病、哮喘、动脉粥样硬化、自体骨髓移植、某些类型的中毒和免疫性肾炎、接触性皮肤超敏反应、炎症性肠病包括溃疡性结肠炎和克罗恩病、炎症性肺病、病毒感染的炎症后遗症、脑膜炎、多发性硬化、多发性骨髓瘤、心肌炎、器官移植、银屑病、肺纤维化、再狭窄、视网膜炎、类风湿性关节炎、化脓性关节炎、中风、肿瘤转移、葡萄膜炎和I型糖尿病。
• [EN] HETEROCYCLE AMIDES AS CELL ADHESION INHIBITORS<br/>[FR] AMIDES HETEROCYCLES COMME INHIBITEURS DE L'ADHESION CELLULAIRE
  申请人：MERCK & CO INC

  公开号：WO2001012183A1

  公开（公告）日：2001-02-22

  Compounds of Formula (I) are antagonists of VLA-4 and/or α4β7, and as such are useful in the inhibition or prevention of cell adhesion and cell-adhesion mediated pathologies. These compounds may be formulated into pharmaceutical compositions and are suitable for use in the treatment of AIDS-related dementia, allergic conjunctivitis, allergic rhinitis, Alzheimer's disease, asthma, atherosclerosis, autologous bone marrow transplantation, certain types of toxic and immune-based nephritis, contact dermal hypersensitivity, inflammatory bowel disease including ulcerative colitis and Crohn's disease, inflammatory lung diseases, inflammatory sequelae of viral infections, meningitis, multiple sclerosis, multiple myeloma, myocarditis, organ transplantation, psoriasis, pulmonary fibrosis, restenosis, retinitis, rheumatoid arthritis, septic arthritis, stroke, tumor metastasis, uveititis, and type I diabetes.

  化合物I的配合物是VLA-4和/或α4β7的拮抗剂，因此可用于抑制或预防细胞粘附和细胞粘附介导的病理反应。这些化合物可以制成药物组合物，适用于治疗艾滋病相关痴呆症、过敏性结膜炎、过敏性鼻炎、阿尔茨海默病、哮喘、动脉粥样硬化、自体骨髓移植、某些类型的毒性和免疫性肾炎、接触性皮肤过敏、炎症性肠病（包括溃疡性结肠炎和克罗恩病）、炎症性肺部疾病、病毒感染后的炎症后遗症、脑膜炎、多发性硬化症、多发性骨髓瘤、心肌炎、器官移植、银屑病、肺纤维化、再狭窄、视网膜炎、类风湿性关节炎、脓毒性关节炎、中风、肿瘤转移、葡萄膜炎和1型糖尿病的治疗。
• US6420418B1
  申请人：——

  公开号：US6420418B1

  公开（公告）日：2002-07-16
• [EN] HERBICIDAL MALONAMIDES<br/>[FR] MALONAMIDES HERBICIDES
  申请人：[en]BASF SE

  公开号：WO2022112351A1

  公开（公告）日：2022-06-02

  The present invention relates to malonamide compounds of the formula (I) wherein the variables are as defined in the claims and the description, and to compositions comprising these compounds. The invention also relates to the use of said malonamide compounds or the corresponding compositions for controlling unwanted vegetation. Furthermore, the invention relates to methods for controlling unwanted vegetation wherein said malonamide compounds or the corresponding compositions are applied.
• Asymmetric Protonation of Lithium Enolate of α-Amino Acid Derivatives using Chiral Brønsted Acids
  作者：Akira Yanagisawa、Yoshihiro Matsuzaki、Hisashi Yamamoto

  DOI：10.1055/s-2001-18754

  日期：——

  Chiral alcohols possessing an asymmetric 2-oxazoline ring were synthesized as new chiral Brønsted acids from tetrahydro-2-furoic acid and (1S,2R)-2-amino-1,2-diphenylethanol. These alcohols were superior to (S,S)- or (R,R)-imide reported previously as a chiral proton source for enantioselective protonation of lithium enolate of an alanine derivative.

  具有不对称2-噁唑烷环的手性醇被合成作为新的手性布朗斯特酸，原料为四氢-2-呋喃酸和(1S,2R)-2-氨基-1,2-二苯乙醇。这些醇在作为手性质子源方面优于之前报道的(S,S)-或(R,R)-酰亚胺，能够用于氨基酸衍生物锂烯醇盐的对映选择性质子化反应。