(4-(2-((tert-butoxycarbonyl)amino)ethyl)phenyl)boronic acid | 1310481-47-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (4-(2-((tert-butoxycarbonyl)amino)ethyl)phenyl)boronic acid
• 英文别名: (4-(((tert-butoxycarbonyl)amino)ethyl)phenyl)boronic acid；4-(N-Boc-aminoethyl)benzeneboronic acid；4-(N-Boc-aminoethyl)phenylboronic acid；[4-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]phenyl]boronic acid
• CAS: 1310481-47-0
• 化学式: C₁₃H₂₀BNO₄
• 分子量: 265.117
• InChiKey: KNYILTVMRTVCDV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.43
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  78.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4-(2-((tert-butoxycarbonyl)amino)ethyl)phenyl)boronic acid 在 4-二甲氨基吡啶 、 水 、 palladium diacetate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 cesium fluoride 、 三氟乙酸 、 2-二环己膦基-2'-(N,N-二甲胺)-联苯 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 为溶剂， 生成 3-(4-(2-(1-(2-methoxyphenyl)cyclopropanecarboxamido)ethyl)phenyl)-N,N,5,7-tetramethylbenzo[b]thiophene-2-carboxamide
  参考文献：
  名称：

  The identification of substituted benzothiophene derivatives as PGE2 subtype 4 receptor antagonists: From acid to non-acid

  摘要：

  We disclose herein our preliminary SAR study on the identification of substituted benzothiophene derivatives as PGE(2) subtype 4 receptor antagonists. A potent EP4 antagonist 6a (K-i = 1.4 nM with 10% HSA) was identified. Furthermore, we found that an acidic group was not essential for the EP4 antagonizing activity in the series and neutral replacements were identified. This opens a new direction for future EP4 antagonist design. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.11.118

文献信息

• Synthesis of <i>ortho</i>-Phenolic Sulfilimines via an Intermolecular Sulfur Atom Transfer Cascade Reaction
  作者：Feng Xiong、Yingying Zuo、Yinan Song、Linxing Zhang、Xinhao Zhang、Shaojian Xu、Yan Ren

  DOI：10.1021/acs.orglett.0c01032

  日期：2020.5.15

  To expand the toolbox for the synthesis of ortho-phenolic sulfilimines, sigmatropic rearrangements were introduced to the field of sulfilimine chemistry. Herein we report a N-H sulfenylation/[2,3]-sigmatropic rearrangement cascade reaction. This mild reaction enables commercially available thiols to serve as the sulfenylation reagent and generates water as the sole byproduct. Moreover, the reaction

  为了扩展用于合成邻苯酚亚硫亚胺的工具箱，将σ重排引入亚硫亚胺化学领域。在这里，我们报告一个NH亚磺酰化/ [2,3] -sigmatropic重排级联反应。这种温和的反应使可商购的硫醇充当亚磺酰化试剂，并产生水作为唯一的副产物。此外，该反应具有广泛的底物范围，并且可以以克规模进行，具有优异的反应效率。
• Dual Directing-Groups-Assisted Redox-Neutral Annulation and Ring Opening of <i>N</i>-Aryloxyacetamides with 1-Alkynylcyclobutanols via Rhodium(III)-Catalyzed C–H/C–C Activations
  作者：Jin-Long Pan、Chang Liu、Chao Chen、Tuan-Qing Liu、Man Wang、Zhenliang Sun、Shu-Yu Zhang

  DOI：10.1021/acs.orglett.9b00812

  日期：2019.4.19

  A cascade [3 + 2] annulation and ring opening of N-aryloxyacetamides with 1-alkynylcyclobutanols via Rh(III)-catalyzed redox-neutral C–H/C–C activations using internal oxidative O–NHAc and −OH as the dual directing groups has been achieved. This reaction provided an efficient and regioselective approach to benzofuran derivatives with good functional group compatibility and high yields.

  级联[3 + 2]与N-芳氧基乙酰胺与1-炔基环丁醇的级联[3 + 2]环化和开环，通过内部氧化O–NHAc和-OH作为双重引导，通过Rh（III）催化的氧化还原中性C–H / C–C活化小组已经实现。该反应为苯并呋喃衍生物提供了一种高效且区域选择性的方法，具有良好的官能团相容性和高收率。
• An internal oxidant-directing strategy enabling transition metal-free C–S bond ligation
  作者：Yingying Zuo、Feng Xiong、Jing Zhao

  DOI：10.1016/j.tet.2019.05.021

  日期：2019.8

  Organic sulfur compounds have broad applications in biology, medicine and material sciences and intensive efforts have been devoted to developing mild and general C-S bond-forming methods. However, a mild, transition-metal-free, direct C-H bond functionalization method remains elusive. Here, we report the use of an internal oxidant-directing strategy to achieve this goal. The cascade reactions described here show excellent chemoselectivity and a wide substrate scope for both oxyamines and sulfenylation reagents. This study enlarges the synthesis toolbox for preparing structurally diverse sulfilimines under mild conditions. (C) 2019 Elsevier Ltd. All rights reserved.