(R)-(tetrahydrofuran-3-yl)hydrazine hydrochloride | 1364632-31-4

• 物质功能分类: 医药中间体 - 杂环化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: (R)-(tetrahydrofuran-3-yl)hydrazine hydrochloride
• 英文别名: [(3R)-tetrahydrofuran-3-yl]hydrazine hydrochloride；(3R)-(Tetrahydro-furan-3-yl)-hydrazine hydrochloride；[(3R)-oxolan-3-yl]hydrazine;hydrochloride
• CAS: 1364632-31-4
• 化学式: C₄H₁₀N₂O*ClH
• 分子量: 138.597
• InChiKey: KUFARIZPHSIGFQ-PGMHMLKASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.34
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  47.3
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-(tetrahydrofuran-3-yl)hydrazine hydrochloride 在 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、2.07 MPa 条件下， 反应 24.0h， 生成 (R)- 3- 氨基四氢呋喃
  参考文献：
  名称：

  Catalytic asymmetric hydrogenation of heterocyclic ketone-derived hydrazones, pronounced solvent effect on the inversion of configuration

  摘要：

  An enantioselective hydrogenation of hydrazones derived from heterocyclic ketones was developed with up to 85% ee. The enantiomeric purity was enriched to >99% ee by crystallization from EtOAc in >80% yield. Optimization studies have revealed a notable solvent effect that resulted in inversion of enantioselectivity from 85% ee in MeOH to -27% ee in DCE. The hydrazone geometry and possible hydrogenation via endocyclic alkene were examined as possible factors for the inversion of enantioselectivity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.05.017
• 作为产物：
  描述：

  (S)-3-羟基四氢呋喃 在 偶氮二甲酸二叔丁酯 、 三苯基膦 、 盐酸 作用下， 以 甲苯 、 1,4-二氧六环 、 甲醇 为溶剂， 反应 64.0h， 以5.4 mmol的产率得到(R)-(tetrahydrofuran-3-yl)hydrazine hydrochloride
  参考文献：
  名称：

  [EN] COMPOUNDS USEFUL AS KINASE INHIBITORS
  [FR] COMPOSÉS UTILISÉS COMME INHIBITEURS DE KINASE

  摘要：

  这项发明涉及新颖的化合物。该发明的化合物是酪氨酸激酶抑制剂。具体来说，该发明的化合物可用作布鲁顿氏酪氨酸激酶（BTK）的抑制剂。该发明还考虑了利用这些化合物治疗通过抑制布鲁顿氏酪氨酸激酶可治疗的疾病，例如癌症、淋巴瘤、白血病和免疫性疾病。

  公开号：

  WO2017103611A1

文献信息

• [EN] COMPOUNDS USEFUL AS KINASE INHIBITORS<br/>[FR] COMPOSÉS UTILISÉS COMME INHIBITEURS DE KINASE
  申请人：REDX PHARMA PLC

  公开号：WO2017103611A1

  公开（公告）日：2017-06-22

  This invention relates to novel compounds. The compounds of the invention are tyrosine kinase inhibitors. Specifically, the compounds of the invention are useful as inhibitors of Bruton's tyrosine kinase (BTK).The invention also contemplates the use of the compounds for treating conditions treatable by the inhibition of Bruton's tyrosine kinase, for example cancer, lymphoma, leukemia and immunological diseases.

  这项发明涉及新颖的化合物。该发明的化合物是酪氨酸激酶抑制剂。具体来说，该发明的化合物可用作布鲁顿氏酪氨酸激酶（BTK）的抑制剂。该发明还考虑了利用这些化合物治疗通过抑制布鲁顿氏酪氨酸激酶可治疗的疾病，例如癌症、淋巴瘤、白血病和免疫性疾病。
• Catalytic asymmetric hydrogenation of heterocyclic ketone-derived hydrazones, pronounced solvent effect on the inversion of configuration
  作者：Nizar Haddad、Bo Qu、Sonia Rodriguez、Lars van der Veen、Diana C. Reeves、Nina C. Gonnella、Heewon Lee、Nelu Grinberg、Shengli Ma、Dhileepkumar Krishnamurthy、Tobias Wunberg、Chris H. Senanayake

  DOI：10.1016/j.tetlet.2011.05.017

  日期：2011.7

  An enantioselective hydrogenation of hydrazones derived from heterocyclic ketones was developed with up to 85% ee. The enantiomeric purity was enriched to >99% ee by crystallization from EtOAc in >80% yield. Optimization studies have revealed a notable solvent effect that resulted in inversion of enantioselectivity from 85% ee in MeOH to -27% ee in DCE. The hydrazone geometry and possible hydrogenation via endocyclic alkene were examined as possible factors for the inversion of enantioselectivity. (C) 2011 Elsevier Ltd. All rights reserved.