(+/-)-methyl-1,2,3,4-tetrahydro-1,4-epoxynaphthalene-1-carboxylate | 221135-49-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (+/-)-methyl-1,2,3,4-tetrahydro-1,4-epoxynaphthalene-1-carboxylate
• 英文别名: methyl 3,4-dihydro-1,4-epoxynaphthalene-1(2H)-carboxylate；methyl 11-oxatricyclo[6.2.1.02,7]undeca-2,4,6-triene-1-carboxylate
• CAS: 221135-49-5
• 化学式: C₁₂H₁₂O₃
• 分子量: 204.225
• InChiKey: RTDPQLZFYFCXED-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-methyl-1,2,3,4-tetrahydro-1,4-epoxynaphthalene-1-carboxylate 在 potassium hydroxide 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 3.0h， 以95%的产率得到1,2,3,4-tetrahydro-1,4-epoxynaphthalene-1-carboxylic acid
  参考文献：
  名称：

  Tetrahydro-1,4-epoxynaphthalene-1-carboxylic acid: a chiral derivatizing agent for the determination of the absolute configuration of secondary alcohols

  摘要：

  A new chiral derivatizing agent, tetrahydro-1,4-epoxynaphthalene-1-carboxylic acid (THENA), with a represented syn-periplanar disposition of O-C(alpha)-C=O as a part of the bicyclic system to lock the aromatic residue conformation and the availability of an internal reference proton for (1)H NMR spectral alignment, is introduced. In the determination of the absolute configuration of chiral secondary alcohols, THENA offered good uniformity of Delta delta with high reliability, resulting in unambiguous assignment of the absolute configuration. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.07.062
• 作为产物：
  描述：

  methyl 1,4-epoxy-1,4-dihydronaphthalene-1-carboxylate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 12.0h， 以97%的产率得到(+/-)-methyl-1,2,3,4-tetrahydro-1,4-epoxynaphthalene-1-carboxylate
  参考文献：
  名称：

  Tetrahydro-1,4-epoxynaphthalene-1-carboxylic acid: a chiral derivatizing agent for the determination of the absolute configuration of secondary alcohols

  摘要：

  A new chiral derivatizing agent, tetrahydro-1,4-epoxynaphthalene-1-carboxylic acid (THENA), with a represented syn-periplanar disposition of O-C(alpha)-C=O as a part of the bicyclic system to lock the aromatic residue conformation and the availability of an internal reference proton for (1)H NMR spectral alignment, is introduced. In the determination of the absolute configuration of chiral secondary alcohols, THENA offered good uniformity of Delta delta with high reliability, resulting in unambiguous assignment of the absolute configuration. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.07.062

文献信息

• [EN] BORONIC ACID DERIVATIVES<br/>[FR] DÉRIVÉS D'ACIDE BORONIQUE
  申请人：MERCK PATENT GMBH

  公开号：WO2019038250A1

  公开（公告）日：2019-02-28

  The present invention relates to a-amino boronic acid derivatives. These compounds are useful for inhibiting the activity of immunoproteasome (LMP7) and for the treatment and/or prevention of medical contidions affected by immunoproteasome activity such as inflammatory and autoimmune diseases, neurodegenerative diseases, proliferative diseases and cancer.

  本发明涉及α-氨基硼酸衍生物。这些化合物对抑制免疫蛋白酶体(LMP7)的活性以及治疗和/或预防受免疫蛋白酶体活性影响的医疗状况，如炎症性和自身免疫疾病、神经退行性疾病、增殖性疾病和癌症，具有用处。
• Boronic acid derivatives
  申请人：Merck Patent GmbH

  公开号：US11274109B2

  公开（公告）日：2022-03-15

  α-amino boronic acid derivatives are useful for inhibiting the activity of immunoproteasome (LMP7) and for the treatment and/or prevention of medical conditions affected by immunoproteasome activity such as inflammatory and autoimmune diseases, neurodegenerative diseases, proliferative diseases and cancer.

  α-氨基硼酸衍生物可用于抑制免疫蛋白酶体（LMP7）的活性，治疗和/或预防受免疫蛋白酶体活性影响的疾病，如炎症和自身免疫性疾病、神经退行性疾病、增殖性疾病和癌症。
• BORONIC ACID DERIVATIVES
  申请人：Merck Patent GmbH

  公开号：EP3672977B1

  公开（公告）日：2022-06-22
• Boronic Acid Derivatives
  申请人：Merck Patent GmbH

  公开号：US20200354382A1

  公开（公告）日：2020-11-12

  α-amino boronic acid derivatives are useful for inhibiting the activity of immunoproteasome (LMP7) and for the treatment and/or prevention of medical conditions affected by immunoproteasome activity such as inflammatory and autoimmune diseases, neurodegenerative diseases, proliferative diseases and cancer.
• Tetrahydro-1,4-epoxynaphthalene-1-carboxylic acid: a chiral derivatizing agent for the determination of the absolute configuration of secondary alcohols
  作者：Suttipun Sungsuwan、Nopporn Ruangsupapichart、Samran Prabpai、Palangpon Kongsaeree、Tienthong Thongpanchang

  DOI：10.1016/j.tetlet.2010.07.062

  日期：2010.9

  A new chiral derivatizing agent, tetrahydro-1,4-epoxynaphthalene-1-carboxylic acid (THENA), with a represented syn-periplanar disposition of O-C(alpha)-C=O as a part of the bicyclic system to lock the aromatic residue conformation and the availability of an internal reference proton for (1)H NMR spectral alignment, is introduced. In the determination of the absolute configuration of chiral secondary alcohols, THENA offered good uniformity of Delta delta with high reliability, resulting in unambiguous assignment of the absolute configuration. (C) 2010 Elsevier Ltd. All rights reserved.