(E)-(R)-2-Hydroxy-pent-3-enenitrile | 10017-08-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (E)-(R)-2-Hydroxy-pent-3-enenitrile
• 英文别名: (r)-2-Hydroxy-3-pentenenitrile；(2R)-2-hydroxypent-3-enenitrile
• CAS: 10017-08-0
• 化学式: C₅H₇NO
• 分子量: 97.1167
• InChiKey: AKXFVHOXDAJSMM-RXMQYKEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  7
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  44
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-(R)-2-Hydroxy-pent-3-enenitrile 在 咪唑 、 二异丁基氢化铝 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成
  参考文献：
  名称：

  Triazole Ureas Act as Diacylglycerol Lipase Inhibitors and Prevent Fasting-Induced Refeeding

  摘要：

  Triazole ureas constitute a versatile class of irreversible inhibitors that target serine hydrolases in both cells and animal models. We have previously reported that triazole ureas can act as selective and CNS-active inhibitors for diacylglycerol lipases (DAGLs), enzymes responsible for the biosynthesis of 2-arachidonoylglycerol (2 -AG) that activates cannabinoid CB1 receptor. Here, we report the enantio- and diastereoselective synthesis and structure-activity relationship studies. We found that 2,4 -substituted triazole ureas with a biphenylmethanol group provided the most optimal scaffold. Introduction of a chiral ether substituent on the 5 -position of the piperidine ring provided ultrapotent inhibitor 38 (DH376) with picomolar activity. Compound 38 temporarily reduces fasting -induced refeeding of mice, thereby emulating the effect of cannabinoid' CB1-receptor inverse agonists. This was mirrored by 39 (DO34) but also by the negative control compound 40 (DO53) (which does not inhibit DAGL), which indicates the triazole ureas may affect the energy balance in mice through multiple molecular targets.

  DOI：

  10.1021/acs.jmedchem.6b01482
• 作为产物：
  描述：

  氢氰酸 、 丁烯-2-醛 在 almond meal 、 citrate buffer pH 5.5 作用下， 以 乙酸乙酯 为溶剂， 以73%的产率得到(E)-(R)-2-Hydroxy-pent-3-enenitrile
  参考文献：
  名称：

  用杏仁粉合成光学活性氰醇

  摘要：

  摘要 醛的不对称氢氰化反应是使用含有酶羟腈酶的杏仁粉完成的。按照简单的程序获得具有高水平对映体纯度的旋光性氰醇。

  DOI：

  10.1080/00397919108021286

文献信息

• Asymmetric synthesis of tetronic acids by Blaise reaction of protected optically active cyanohydrins
  作者：Jonathan J. Duffield、Andrew C. Regan

  DOI：10.1016/0957-4166(96)00059-6

  日期：1996.3

  An asymmetric synthesis of tetronic acids is described, involving the Blaise reaction of Reformatsky reagents with silyl-protected optically active cyanohydrins, which were prepared by an enzyme-catalysed method. (C) 1996 Elsevier Science Ltd
• Asymmetric cyanohydrin formation from aldehydes catalyzed by manganese Schiff base complexes
  作者：Yanyang Qu、Linhai Jing、Zhiqing Wu、Di Wu、Xiangge Zhou

  DOI：10.1016/j.tetasy.2010.01.009

  日期：2010.2

  The catalyst generated in situ from Mn(OAc)(2) and a chiral Schiff base ligand exhibited excellent catalytic abilities in asymmetric cyanohydrin formation from aldehydes with sodium cyanide in up to 99% enantioselectivity and good yield. (C) 2010 Elsevier Ltd. All rights reserved.