dihydroxy-[1]naphthylmethyl-borane | 86819-97-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: dihydroxy-[1]naphthylmethyl-borane
• 英文别名: Dihydroxy-[1]naphthylmethyl-boran；(Naphthalen-1-ylmethyl)boronic acid；naphthalen-1-ylmethylboronic acid
• CAS: 86819-97-8
• 化学式: C₁₁H₁₁BO₂
• 分子量: 186.018
• InChiKey: GGNGMAHIWPBGHO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.39
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-N-((R)-7-bromo-1,2,3,4-tetrahydronaphthalen-1-yl)-2-methylpropane-2-sulfinamide 、 dihydroxy-[1]naphthylmethyl-borane 在 4,4,5,5-四甲基-2-(萘-2-甲基)-1,3,2-二噁硼烷 、 potassium carbonate 作用下， 以 水 、 丙酮 为溶剂， 反应 1.0h， 以20.2%的产率得到(R)-2-methyl-N-((R)-7-(naphthalen-1-ylmethyl)-1,2,3,4-tetrahydronaphthalen-1-yl)propane-2-sulfinamide
  参考文献：
  名称：

  Further Optimization and Evaluation of Bioavailable, Mixed-Efficacy μ-Opioid Receptor (MOR) Agonists/δ-Opioid Receptor (DOR) Antagonists: Balancing MOR and DOR Affinities

  摘要：

  In a previously described peptidomimetic series, we reported the development of bifunctional ?-opioid receptor (MOR) agonist and delta-opioid receptor (DOR) antagonist ligands with a lead compound that produced antinociception for 1 h after intraperitoneal administration in mice. In this paper, we expand on our original series by presenting two modifications, both of which were designed with the following objectives: (1) probing bioavailability and improving metabolic stability, (2) balancing affinities between MOR and DOR while reducing affinity and efficacy at the kappa-opioid receptor (KOR), and (3) improving in vivo efficacy. Here, we establish that, through N-acetylation of our original peptidomimetic series, we are able to improve DOR affinity and increase selectivity relative to KOR while maintaining the desired MOR agonist/DOR antagonist profile. From initial in vivo studies, one compound (14a) was found to produce dose-dependent antinociception after peripheral administration with an improved duration of action of longer than 3 h.

  DOI：

  10.1021/acs.jmedchem.5b01270
• 作为产物：
  描述：

  硼酸三丁酯 、 alkaline earth salt of/the/ methylsulfuric acid 生成 dihydroxy-[1]naphthylmethyl-borane
  参考文献：
  名称：

  Lawesson, Arkiv foer Kemi, 1957, vol. 10, p. 171,172,175

  摘要：

  DOI：

文献信息

• Chiral diene-promoted room temperature conjugate arylation: highly enantioselective synthesis of substituted chiral phenylalanine derivatives and α,α-di(arylmethyl)acetates
  作者：Jian-Ping Chen、Ming-Hua Xu

  DOI：10.1039/d0ob00616e

  日期：——

  highly enantiocontrolled room temperature rhodium-catalyzed conjugate arylation process was developed. The reaction proceeds through 1,4-addition of α-substituted acrylates followed by enantioselective protonation using a C1-symmetric chiral bicyclo[2,2,2] diene as the ligand and water as the proton source. This exceptionally simple protocol provides a reliable and practical access to structurally important

  开发了高度对映体控制的室温铑催化的共轭芳基化方法。反应通过1，4-加成α-取代的丙烯酸酯，然后使用C 1对称手性双环[2,2,2]二烯作为配体和水作为质子源进行对映选择性质子化而进行。这种非常简单的方案可以以高收率（高达99％）和良好至极好的ee值（高达99％）可靠且实用地获得结构上重要的苯丙氨酸衍生物和α，α-二（芳基甲基）乙酸酯。