4-(3-hydroxy-1-propenyl)benzoic acid methyl ester | 87808-23-9

• 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-(3-hydroxy-1-propenyl)benzoic acid methyl ester
• 英文别名: 4-(3-hydroxy-propenyl)-benzoic acid methyl ester；Methyl 4-(3-hydroxy-1-propenyl)-benzoate；methyl 4-(3-hydroxyprop-1-enyl)benzoate
• CAS: 87808-23-9
• 化学式: C₁₁H₁₂O₃
• 分子量: 192.214
• InChiKey: PSCVJQSMSDQKBF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(3-hydroxy-1-propenyl)benzoic acid methyl ester 在 三溴化磷 作用下， 生成 Methyl 4-(3-bromoprop-1-enyl)benzoate
  参考文献：
  名称：

  铜催化的烯丙基卤的亲核三氟甲基化：烯丙基三氟甲基化的简单方法

  摘要：

  三氟甲基化：在催化量的噻吩-2-羧酸铜（I）的存在下，用三氟甲基三甲基硅烷处理烯丙基卤化物可得到相应的烯丙基三氟甲基化产物，产率高至高且具有完全的区域选择性（参见方案）。使用THF作为溶剂对于获得良好的产物收率至关重要。

  DOI：

  10.1002/chem.201202853
• 作为产物：
  描述：

  4-(3-羟基-1-丙炔)苯甲酸甲酯 在 氢气 作用下， 以 甲苯 为溶剂， 生成 4-(3-hydroxy-1-propenyl)benzoic acid methyl ester
  参考文献：
  名称：

  铜催化的 [2,3]- 和 [1,2]- 碘鎓叶立德重排中配体控制的区域发散

  摘要：

  尽管烯丙基叶立德重排对于复杂分子的合成很重要，[2,3]-和[1,2]-重排的催化剂控制仍然是一个未解决的问题。我们开发了第一个由带有不同配体的铜催化剂控制的碘鎓叶立德的区域发散[2,3]-和[1,2]-重排。在 2,2'-联吡啶配体存在下，重氮酯和烯丙基碘通过 [2,3]-重排途径发生反应。或者，膦配体有利于形成[1,2]-重排产物。以高产率、区域选择性和非对映选择性获得了一系列含有广泛官能团的 α-碘酯。氘标记研究表明区域选择性重排的不同机制。

  DOI：

  10.1021/jacs.6b08624

文献信息

• Palladium‐Catalyzed Asymmetric C(sp ³ )−H Allylation of 2‐Alkylpyridines
  作者：Ryo Murakami、Kentaro Sano、Tomohiro Iwai、Tohru Taniguchi、Kenji Monde、Masaya Sawamura

  DOI：10.1002/anie.201802821

  日期：2018.7.20

  The palladium‐catalyzed asymmetric side‐chain C(α)‐allylation of 2‐alkylpyridines, without using an external base, was developed. The high linear selectivities and enantioselectivities were achieved using new chiral diamidophosphite monodentate ligands. Given that the reaction conditions do not require an external base, this catalyst system enabled chemoselective C(α)‐allylation of 2‐alkylpyridines

  在不使用外部碱的情况下，开发了钯催化的2-烷基吡啶的不对称侧链C（α）烯丙基化。使用新的手性二氨基亚磷酸酯单齿配体可实现高线性选择性和对映选择性。考虑到反应条件不需要外部碱，该催化剂体系可以使含α-羰基CH键的2-烷基吡啶的化学选择性C（α）烯丙基化，而α-羰基CH键的酸性比α-吡啶基CH键的酸性高。
• Pyrazolopyrimidine compound and a process for preparing the same
  申请人：Takamuro Iwao

  公开号：US20060135525A1

  公开（公告）日：2006-06-22

  The present invention provides a novel pyrazolopyrimidine compound of the formula [I]: wherein R′ is (A) a substituted aryl group, (B) an optionally substituted nitrogen-containing aliphatic heteromonocyclic group, (C) a substituted cyclo-lower alkyl group, (D) an optionally substituted amino group, or (E) a substituted heteroaryl group, R 2 is (a) an optionally substituted heteroaryl group or (b) an optionally substituted aryl group, Y is a single bond, a lower alkylene group or a lower alkenylene group, Z is a group of the formula: —CO—, —CH2-, S02- or a group of the formula [II]: Q is a lower alkylene group, and q is an integer of 0 or 1 or a pharmaceutically acceptable sait thereof, which has a small conductance potassium channel (SK channel) blocking activity and is useful as a medicament and a process for preparing the same.

  本发明提供了一种新型的吡唑嘧啶化合物，其化学式为[I]：其中R′为（A）取代芳基，（B）可选取代的含氮脂肪杂环基，（C）取代的环低烷基，（D）可选取代的氨基或（E）取代的杂环芳基；R2为（a）可选取代的杂环芳基或（b）可选取代的芳基；Y为单键，低碳基烷基或低碳基烯基；Z为式[II]的基团：其中Q为低碳基烷基，q为0或1的整数，或其药学上可接受的盐。该化合物具有小电导钾通道（SK通道）阻滞活性，并可作为药物使用，以及其制备方法。
• Lewis Base-Catalyzed Trifluoromethylsulfinylation of Allylic Alcohols: Stability-Oriented Divergent Synthesis
  作者：Shuya Xing、Cheng Ma、Wen Liu、Shao-Fei Ni、Dianhu Zhu、Li-Wen Xu、Xinxin Shao

  DOI：10.1021/acs.orglett.2c04243

  日期：2023.2.24

  A novel strategy is demonstrated for Lewis base-activated trifluoromethylsulfinylation of allylic alcohols. Controllable synthesis of structurally varied allylic trifluoromethanesulfones via sigmatropic rearrangements was performed, and trifluoromethanesulfinate esters were achieved. This metal-free, catalytic divergent transformation features good functional group tolerance and late-stage modification

  展示了路易斯碱激活的烯丙醇三氟甲基亚磺酰化的新策略。通过 sigmatropic 重排可控合成结构多样的烯丙基三氟甲砜，并获得了三氟甲亚磺酸酯。这种无金属催化发散转化具有良好的官能团耐受性和生物活性分子的后期修饰。机理研究表明，路易斯碱与N -(三氟甲基亚磺酰基)邻苯二甲酰亚胺相互作用，生成离子对加合物，然后与烯丙醇进行 O-三氟甲基亚磺酰化。
• Enantioselective Sulfonium–Claisen Rearrangement with Cinnamyl Thioethers
  作者：Jiwon Jang、Youngjin Bae、Seunghoon Shin

  DOI：10.1021/acs.orglett.3c01244

  日期：2023.6.2

  Sulfonium–Claisen rearrangement leveraged by the gold-catalyzed formation of allyl sulfonium intermediates has enabled an exceptional level of regio- and enantiocontrol for the synthesis of skipped 1,4-dienes. However, the application of cinnamyl thioether derivatives to the sulfonium–Claisen rearrangement has been unsuccessful so far due to the extensive dissociation of the cinnamyl cation. By fine-tuning

  金催化形成烯丙基硫中间体所利用的硫 - 克莱森重排使跳过的 1,4-二烯合成具有特殊水平的区域和对映控制。然而，由于肉桂基阳离子的广泛解离，迄今为止，肉桂基硫醚衍生物在硫-克莱森重排中的应用一直没有成功。通过微调双膦配体，我们能够使肉桂基硫醚参与 [3,3]-σ 重排，以高度对映选择性的方式并以良好的产率提供所需的 1,4-二烯。所得产物可转化为具有乙烯基部分的光学活性 2-色满酮和 4 H-色烯。
• Discovery of Potent Benzofuran-Derived Diapophytoene Desaturase (CrtN) Inhibitors with Enhanced Oral Bioavailability for the Treatment of Methicillin-Resistant <i>Staphylococcus aureus</i> (MRSA) Infections
  作者：Youxin Wang、Feifei Chen、Hongxia Di、Yong Xu、Qiang Xiao、Xuehai Wang、Hanwen Wei、Yanli Lu、Lingling Zhang、Jin Zhu、Chunquan Sheng、Lefu Lan、Jian Li

  DOI：10.1021/acs.jmedchem.5b01984

  日期：2016.4.14

  Blocking the staphyloxanthin biosynthesis process has emerged as a new promising antivirulence strategy. Previously, we first revealed that CrtN is a druggable target against infections caused by pigmented Staphylococcus aureus (S. aureus) and that naftifine was an effective CrtN inhibitor. Here, we identify a new type of benzofuran-derived CrtN inhibitor with submicromolar IC50 values that is based on the naftifine scaffold. The most potent analog, 5m, inhibits the pigment production of S. aureus Newman and three MRSA strains, with IC50 values of 0.38-5.45 nM, without any impact on the survival of four strains (up to 200 mu M). Notably, compound 5m (1 mu M) could significantly sensitize four strains to immune clearance and could effectively attenuate the virulence of three strains in vivo. Moreover, 5m was determined to be a weak antifungal reagent (MIC > 16 mu g/mL). Combined with good oral bioavailability (F = 42.2%) and excellent safety profiles, these data demonstrate that 5m may be a good candidate for the treatment of MRSA infections.