(R)-tetrahydrofuran-3-carbonitrile | 1363378-15-7

• 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-carbonitrile
• 英文别名: (3R)-oxolane-3-carbonitrile
• CAS: 1363378-15-7
• 化学式: C₅H₇NO
• 分子量: 97.1167
• InChiKey: OANDNNNKGULGJK-RXMQYKEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  33
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-tetrahydrofuran-3-carbonitrile 在 盐酸羟胺 、 potassium carbonate 作用下， 以 水 、 异丙醇 为溶剂， 以65 %的产率得到(3R)-N'-hydroxyoxolane-3-carboximidamide
  参考文献：
  名称：

  BENZAZEPINE DERIVATIVES, COMPOSITIONS, AND METHODS FOR TREATING COGNITIVE IMPAIRMENT

  摘要：

  Benzazepine derivatives of Formula (I), compositions comprising therapeutically effective amounts of those benzazepine derivatives and methods of using those derivatives or compositions in treating cognitive impairment associated with central nervous system (CNS) disorders or associated with risk factors for cognitive impairment. In particular, it relates to the use of a αs-containing GABAAR agonist (e.g., a as-containing GABAAR positive allosteric modulator) in treating cognitive impairment associated with central nervous system (CNS) disorders or having a risk factor associated with cognitive impairment in a subject in need or at risk thereof, including, without limitation, subjects having or at risk for age-related cognitive impairment, Mild Cognitive Impairment (MCI), amnestic MCI (aMCI), Age-Associated Memory Impairment (AAMI), Age Related Cognitive Decline (ARCD), dementia, Alzheimer's Disease(AD), prodromal AD, post-traumatic stress disorder (PTSD), schizophrenia, bipolar disorder, amyotrophic lateral sclerosis (ALS), cancer-therapy-related cognitive impairment, mental retardation, Parkinson's disease (PD), autism spectrum disorders, fragile X disorder, Rett syndrome, compulsive behavior, and substance addiction. It also relates to the use of a as-containing GABAAR agonist (e.g., a as-containing GABAAR positive allosteric modulator) as described herein in treating brain cancers (including brain tumors, e.g., medulloblastomas), and cognitive impairment associated therewith.

  公开号：

  WO2024039886A1
• 作为产物：
  描述：

  3-oximinomethyltetrahydrofuran 在 aldoxime dehydratase from Bacillus sp. OxB-1 作用下， 以 二甲基亚砜 为溶剂， 反应 2.0h， 生成 (3S)-氧戊烷-3-腈 、 (R)-tetrahydrofuran-3-carbonitrile
  参考文献：
  名称：

  腈的无氰对映选择性合成：生物催化概念的合成证明和机理见解

  摘要：

  据报道，第一种（“定义上”）无氰化物的手性α-和β-支化腈的对映选择性合成方法。该过程是基于醛糖肟脱水酶对外消旋醛肟的生物催化脱水作用，当从具有高E /的外消旋底物开始时，水是唯一的副产物，具有高转化率和出色的对映选择性（高达98％ee）。ž比率。因此，与通过容易获得的醛与羟胺缩合而容易产生醛肟的方法相结合，该方法为在水溶液中具有优异原子经济性的手性腈提供了引人入胜且有效的途径。此外，该研究显示了对映体对醛糖肟部分的E或Z构型的令人惊讶的酶促依赖性。值得注意的是，该酶促反应的整个立体化学过程已经通过计算研究得以合理化。

  DOI：

  10.1002/cctc.201402612

文献信息

• Cyanide-free Enantioselective Synthesis of Nitriles: Synthetic Proof of a Biocatalytic Concept and Mechanistic Insights
  作者：Richard Metzner、Seiji Okazaki、Yasuhisa Asano、Harald Gröger

  DOI：10.1002/cctc.201402612

  日期：2014.11

  chiral α‐ and β‐branched nitriles is reported. This process is based on a biocatalytic dehydration of racemic aldoximes by using an aldoxime dehydratase and proceeds with high conversion and excellent enantioselectivity (up to 98 % ee) with water as the only side‐product when starting from a racemic substrate with a high E/Z ratio. Thus, in combination with the facile generation of aldoximes through

  据报道，第一种（“定义上”）无氰化物的手性α-和β-支化腈的对映选择性合成方法。该过程是基于醛糖肟脱水酶对外消旋醛肟的生物催化脱水作用，当从具有高E /的外消旋底物开始时，水是唯一的副产物，具有高转化率和出色的对映选择性（高达98％ee）。ž比率。因此，与通过容易获得的醛与羟胺缩合而容易产生醛肟的方法相结合，该方法为在水溶液中具有优异原子经济性的手性腈提供了引人入胜且有效的途径。此外，该研究显示了对映体对醛糖肟部分的E或Z构型的令人惊讶的酶促依赖性。值得注意的是，该酶促反应的整个立体化学过程已经通过计算研究得以合理化。
• BENZAZEPINE DERIVATIVES, COMPOSITIONS, AND METHODS FOR TREATING COGNITIVE IMPAIRMENT
  申请人：[en]AGENEBIO, INC.

  公开号：WO2024039886A1

  公开（公告）日：2024-02-22

  Benzazepine derivatives of Formula (I), compositions comprising therapeutically effective amounts of those benzazepine derivatives and methods of using those derivatives or compositions in treating cognitive impairment associated with central nervous system (CNS) disorders or associated with risk factors for cognitive impairment. In particular, it relates to the use of a αs-containing GABAAR agonist (e.g., a as-containing GABAAR positive allosteric modulator) in treating cognitive impairment associated with central nervous system (CNS) disorders or having a risk factor associated with cognitive impairment in a subject in need or at risk thereof, including, without limitation, subjects having or at risk for age-related cognitive impairment, Mild Cognitive Impairment (MCI), amnestic MCI (aMCI), Age-Associated Memory Impairment (AAMI), Age Related Cognitive Decline (ARCD), dementia, Alzheimer's Disease(AD), prodromal AD, post-traumatic stress disorder (PTSD), schizophrenia, bipolar disorder, amyotrophic lateral sclerosis (ALS), cancer-therapy-related cognitive impairment, mental retardation, Parkinson's disease (PD), autism spectrum disorders, fragile X disorder, Rett syndrome, compulsive behavior, and substance addiction. It also relates to the use of a as-containing GABAAR agonist (e.g., a as-containing GABAAR positive allosteric modulator) as described herein in treating brain cancers (including brain tumors, e.g., medulloblastomas), and cognitive impairment associated therewith.