3-cyclopentylprop-2-en-1-ol | 154081-25-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-cyclopentylprop-2-en-1-ol
• 英文别名: -3-cyclopentylprop-2-en-1-ol；trans-3-cyclopentylprop-2-en-1-ol；(E)-3-cyclopentylprop-2-en-1-ol；3t-cyclopentyl-allyl alcohol；3t-Cyclopentyl-allylalkohol
• CAS: 154081-25-1
• 化学式: C₈H₁₄O
• 分子量: 126.199
• InChiKey: FYOMDMAJOTWCGR-ZZXKWVIFSA-N

物化性质

• 沸点：
  207.1±8.0 °C(Predicted)
• 密度：
  1.033±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-cyclopentylprop-2-en-1-ol 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 molecular sieve 、 D-(-)-酒石酸二乙酯 作用下， 以 异辛烷 、 二氯甲烷 为溶剂， 反应 48.0h， 生成 ((2R,3R)-3-Cyclopentyl-oxiranyl)-methanol
  参考文献：
  名称：

  环状环砜作为HIV-1蛋白酶抑制剂的新型和高亲和力P2配体的发展。

  摘要：

  描述并设计了一系列新的蛋白酶抑制剂，这些蛋白酶抑制剂结合了针对HIV-1蛋白酶S2底物结合位点的构象受限的环状配体。我们最近报道了3-四氢呋喃基的氨基甲酸酯作为HIV-1蛋白酶抑制剂的P2配体。随后，我们发现3（S）-羟基环丁砜的氨基甲酸酯进一步增加了这些抑制剂的体外效能。此外，在任一杂环系统的3-羟基上引入小的2-烷基顺式进一步增强了酶亲和力。迄今为止，顺-2-异丙基提供了最佳的抑制性能。这导致发现了抑制剂43（IC50 3.5 nM，与目前的临床候选药物1（Ro 31-8959）具有相似的体外抗病毒效力（CIC95 50 +/- 14 nM），但由于排除了P3喹啉配体，分子量降低。另外，已经证明八氢吡啶并衍生物34是P1'十氢异喹啉衍生物的有效替代物。

  DOI：

  10.1021/jm00034a016
• 作为产物：
  描述：

  (E)-3-环戊基丙烯醛 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 3-cyclopentylprop-2-en-1-ol
  参考文献：
  名称：

  Novel Terminal Bipheny-Based Diapophytoene Desaturases (CrtN) Inhibitors as Anti-MRSA/VISR/LRSA Agents with Reduced hERG Activity

  摘要：

  CrtN has been identified as an attractive and druggable target for treating pigmented Staphylococcus aureus infections. More than 100 new compounds were synthesized, which target the overwhelming the defects of the CrtN inhibitor 1. Analogues 23a and 23b demonstrated a significant activity against pigmented S. aureus Newman and 13 MRSA strains (IC50 = 0.02-10.5 nM), along with lower hERG inhibition (IC50 > 30 mu M, similar to 10-fold decrease in comparison with 1). Furthermore, 23a and 23b were confirmed to reduce the staphylococcal load in the kidney and heart in a mouse model with normal treatment deeper than pretreatment ones, comparable even with vancomycin and linezolid. Remarkably, 23a could strongly block the pigment biosynthesis of these nine multidrug-resistant MRSA strains, including excellent activity against LRSA strains and VISA strains in vivo, and all of which demonstrated that 23a has a huge potential against intractable MRSA, VISA, and LRSA issues as a therapeutic drug.

  DOI：

  10.1021/acs.jmedchem.7b01300

文献信息

• Enantioselective α- and γ-Alkylation of α,β-Unsaturated Aldehydes Using Dienamine Activation
  作者：Julian Stiller、Eugenia Marqués-López、Raquel P. Herrera、Roland Fröhlich、Carsten Strohmann、Mathias Christmann

  DOI：10.1021/ol102559f

  日期：2011.1.7

  The enantioselective alkylation of α,β-unsaturated aldehydes with stabilized carbocations as electrophiles via the activation as dienamine intermediates is described. This unique application of dienamine catalysis allows for the first enantioselective γ-alkylation of linear α,β-unsubstituted enals.

  描述了通过活化为二烯胺中间体，以稳定的碳阳离子作为亲电子体的α，β-不饱和醛的对映选择性烷基化。二烯胺催化的这种独特应用使线性α，β-未取代的烯醛首次对映选择性γ-烷基化。
• Ligand-controlled cobalt-catalyzed remote hydroboration and alkene isomerization of allylic siloxanes
  作者：Pei Zhao、Jiaxin Huang、Jie Li、Kezhuo Zhang、Wen Yang、Wanxiang Zhao

  DOI：10.1039/d1cc05964e

  日期：——

  The Co-catalyzed remote hydroboration and alkene isomerization of allylic siloxanes were realized by a ligand-controlled strategy. The remote hydroboration with dcype provided borylethers, while xantphos favored the formation of silyl enol ethers.

  烯丙基硅氧烷的共催化远程硼氢化和烯烃异构化是通过配体控制的策略实现的。用 dcype 进行远程硼氢化反应提供硼醚，而 xantphos 有利于形成甲硅烷基烯醇醚。
• Highly general synthesis of [E]- and [Z]-3-alkylsubstituted allylboronates via one-carbon homologation of stereospecific 1-alken-1-ylboronates
  作者：Herbert C. Brown、Avinash S. Phadke、Narayan G. Bhat

  DOI：10.1016/s0040-4039(00)61491-0

  日期：1993.12

  Stereospecific 1-alken-1-ylboronates readily react with in situ generated chloromethyllithium, producing the corresponding allylboronate in good yields and in excellent stereochemical purities. These are very important synthetic intermediates and conversion of a representative derivative, [E]-2-(2-heptenyl)-1,3,2-dioxaborinane, 2 (R1 = C4H9, R2 = R3 = H), into several compounds of synthetic interest

  立体特异性的1-烯-1-基硼酸酯易于与原位生成的氯甲基锂反应，以良好的产率和优异的立体化学纯度产生相应的烯丙基硼酸酯。这些是非常重要的合成中间体，是代表性衍生物[ E ] -2-（2-庚烯基）-1,3,2-二氧杂硼烷2（R 1 = C 4 H 9，R 2 = R 3 = H ），描述了几种具有合成意义的化合物。
• OPTICALLY ACTIVE AXIALLY CHIRAL ALPHA-ALLENIC ALCOHOL, SYNTHESIS METHOD AND USE THEREOF
  申请人：SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY, CHINESE ACADEMY OF SCIENCES

  公开号：US20150105567A1

  公开（公告）日：2015-04-16

  The present invention relates to an optically active axially chiral α-allenic alcohol, a synthetic method and use thereof. A method of preparing a high optically active chiral α-allenic alcohol by using propargyl alcohol, aldehyde and chiral α,α-diphenyl-L-prolinol under the protection of tert-butyldimethylsilyl with a mediator zinc bromide. The axially chiral α-allenic alcohol has the structural formula (I). The method of the present invention has the following advantages: the synthesis route is short, operations are simple, raw materials are readily available, separation and purification are convenient, the substrate has high generality, the total yield is high, and enantioselectivity and diastereoselectivity are high. The high optically active axially chiral α-allenic alcohol synthesized by adopting the method of the present invention can conveniently synthesize 2,5-dihydrofuran compounds having central chirality via complete chirality transfer, and at the same time can further be used to synthesize axially chiral allenic amine and allenic malonate compounds without reacemization.

  本发明涉及一种光学活性轴向手性α-亚烯醇，其合成方法和用途。通过在叔丁基二甲基硅保护下使用丙炔醇、醛和手性α,α-二苯基-L-脯氨醇，在锌溴化物介质的保护下制备高光学活性手性α-亚烯醇的方法。轴向手性α-亚烯醇的结构式为（I）。本发明的方法具有以下优点：合成路线短，操作简单，原料易得，分离和纯化方便，底物通用性高，总收率高，并且对映选择性和对映异构选择性高。采用本发明方法合成的高光学活性轴向手性α-亚烯醇可以通过完全手性转移方便地合成具有中心手性的2,5-二氢呋喃化合物，同时还可以进一步用于合成轴向手性亚烯胺和亚烯丙二酸酯化合物而不发生消旋。
• Benzothiozinone derivatives with anti-tubercular Activity−Further side chain investigation
  作者：Xiaomei Wu、Wenxin Wang、Giovanni Stelitano、Olga Riabova、Bin Wang、Wei Niu、Mario Cocorullo、Rui Shi、Laurent R. Chiarelli、Vadim Makarov、Yu Lu、Chuan Li、Chunhua Qiao

  DOI：10.1016/j.ejmech.2023.115976

  日期：2024.1

  A series of novel benzothiozinone (BTZ) derivatives were designed, prepared and evaluated for antituberculosis activity. Specifically, the BTZ pharmacophore is retained and the previous heterocyclic ring linker is replaced by alkynyl or vinyl linker, the resulting compounds displayed about 5−fold improved antimycobacterial activity. We further revealed that the linker attached tail group affects the

  设计、制备了一系列新型苯并噻嗪酮（BTZ）衍生物并评估其抗结核活性。具体而言，保留 BTZ 药效团，并用炔基或乙烯基连接基取代先前的杂环连接基，所得化合物显示出约 5 倍的抗分枝杆菌活性。我们进一步揭示，尾部连接基团会影响化合物的代谢稳定性、效力和其他药物特性。这项工作发现了两种具有可接受的低 MIC 和改善的代谢稳定性的化合物（ A1和A11 ）。代表性化合物A11在急性结核感染小鼠模型中表现出杀菌功效。