4-(but-3-en-1-ol)pyridine | 17285-59-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 4-(but-3-en-1-ol)pyridine
• 英文别名: (RS)-1-(4-pyridyl)but-3-en-1-ol；1-(pyridin-4-yl)but-3-en-1-ol；1-(4-pyridyl)-3-buten-1-ol；1-(pyridin-4-yl)-3-buten-1-ol；1-pyridin-4-ylbut-3-en-1-ol
• CAS: 17285-59-5
• 化学式: C₉H₁₁NO
• 分子量: 149.192
• InChiKey: WEPJYMIOJMZLBS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(but-3-en-1-ol)pyridine 在 正丁基锂 、 氨 、 双氧水 、 臭氧 、 4-苯偶氮二苯胺 、 三氯氧磷 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.33h， 生成 cis-2--4-hydroperoxy-6-(4-pyridyl)tetrahydro-2H-1,3,2-oxazaphosphorine 2-oxide
  参考文献：
  名称：

  Synthesis and antitumor properties of activated cyclophosphamide analogs

  摘要：

  A series of 5- and 6-substituted cyclophosphamide analogues has been prepared, and their P-31 NMR kinetics of phosphoramide mustard (PDA) release and in vitro and in vivo cytotoxicity have been evaluated. cis-4-Hydroxy-5-methoxycyclophosphamide equilibrated very slowly and to a minor extent with the ring-opened aldophosphamide analogues in aqueous buffer; release of PDA was observed to a minor extent and only at high (1 M) buffer concentrations. This analogue was essentially inactive in vitro against L1210 and P388 leukemia cells. 6-Phenylcyclophosphamide and its 4-hydroperoxy derivative were potent inhibitors of blood acetylcholinesterase and were lethal at therapeutic doses in mice. In contrast, 4-hydroperoxy-6-(4-pyridyl)cyclophosphamide did not inhibit acetylcholinesterase and showed significant antitumor activity in vitro and in vivo against both wild-type and cyclophosphamide-resistant L1210 leukemia. The 4-hydroperoxy-6-arylcyclophosphamides were generally active in vitro against both wild-type and cyclophosphamide-resistant L1210 and P388 cells, and several analogues showed significant activity in vivo. Surprisingly, there was no correlation between antitumor activity in vitro and the rate of PDA release in aqueous buffer. Several compounds that showed essentially no release of PDA in aqueous buffer over several hours were highly cytotoxic to leukemia cells following a 1-h exposure in vitro. These results show that activated cyclophosphamide analogues substituted at the 6-position are not cross-resistant in these leukemia cell lines, and that a specific intracellular activation mechanism may be catalyzing PDA release in these analogues.

  DOI：

  10.1021/jm00114a013
• 作为产物：
  描述：

  4-氯甲基吡啶盐酸盐 在 sodium amide 、 烯丙醇 、 xylene 作用下， 生成 4-(but-3-en-1-ol)pyridine
  参考文献：
  名称：

  Suzuki, Pharmaceutical Bulletin, 1956, vol. 4, p. 479,481

  摘要：

  DOI：

文献信息

• Silver Oxide as a Novel Catalyst for Carbon–Carbon Bond-forming Reactions in Aqueous Media
  作者：Masaharu Ueno、Arata Tanoue、Shu Kobayashi

  DOI：10.1246/cl.2010.652

  日期：2010.6.5

  Silver oxide was found to be an excellent catalyst for allylation reactions of allyltributyltins with aldehydes in aqueous media. Despite the very low solubility of silver oxide in the media, the reactions proceeded smoothly, and the catalyst was recovered and reused. When α-methyl-substituted allyltributyltin was used as the nucleophile, the corresponding α-adducts were obtained exclusively in high yields with good anti-selectivity. A reaction mechanism including transmetalation from tin to silver is proposed.

  银氧化物在烯丙基三丁锡与醛在水相中的烯丙基化反应中表现出优异的催化性能。尽管银氧化物在介质中的溶解度极低，反应仍顺利进行，且催化剂可回收并重复使用。当使用α-甲基取代的烯丙基三丁锡作为亲核试剂时，以高产率且具有良好反式选择性地获得了相应的α-加成产物。提出了一种包含从锡到银的转金属化步骤的反应机理。
• Copper‐Impregnated Magnesium‐Lanthanum Mixed Oxide: A Reusable Heterogeneous Catalyst for Allylation of Aldehydes and Ketones
  作者：Jaya Pogula、Soumi Laha、B. Sreedhar、Pravin R. Likhar

  DOI：10.1002/adsc.201901133

  日期：2020.3.4

  Copper‐impregnated magnesium‐lanthanum mixed oxide [Cu(II)/Mg−La] was used as catalyst in synthesis of homoallylic alcohols from aldehydes and ketones using allyltributylstannane as the allylating source. The present protocol provides a great application potential for the synthesis of corresponding allyl alcohols with excellent yields and selectivity. The catalyst exhibits broad functional group compatibility

  铜浸渍的镁镧混合氧化物[Cu（II）/ Mg-La]用作催化剂，使用烯丙基三丁基锡烷作为烯丙基化来源，由醛和酮合成均丙醇。本方案为以优异的产率和选择性合成相应的烯丙醇提供了巨大的应用潜力。该催化剂与各种取代的醛和酮具有广泛的官能团相容性，可在非均相条件下以高收率提供所需的产物。重要的是，可以通过离心从反应混合物中回收多相催化剂，并使用多达三个循环。
• Pyridine Radicals in Synthesis. Part 3: Cyclopentannulation of Pyridine via the 3-Pyridyl Radical and a Formal Synthesis of (±)-Oxerine
  作者：Keith Jones、Andrea Fiumana、Maria L Escudero-Hernandez

  DOI：10.1016/s0040-4020(99)00999-0

  日期：2000.1

  zinc-mediated Barbier conditions is described. The homoallylic alcohols produced are cyclised via the derived 3-pyridyl radical to give cyclopentannulated pyridines. One of these bicyclic compounds is converted into an advanced intermediate in a previous synthesis of the monoterpene alkaloid (±)-oxerine.

  描述了在锌介导的Barbier条件下3-溴-4-甲酰基吡啶的烯丙基化和炔丙基化。通过衍生的3-吡啶基将产生的均烯丙基醇环化，得到环戊环化吡啶。这些双环化合物之一在先前的单萜生物碱（±）-氧杂环丁烷合成中被转化为高级中间体。
• Chemoenzymatic synthesis of optically active heterocyclic homoallylic and homopropargylic alcohols
  作者：Satwinder Singh、Subodh Kumar、Swapandeep Singh Chimni

  DOI：10.1016/s0957-4166(02)00743-7

  日期：2002.12

  A chemoenzymatic methodology has been developed using indium-mediated allylation of heterocyclic aldehydes under aqueous conditions followed by Pseudomonas cepacia lipase-catalyzed enantioselective acylation of racemic homoallylic and homopropargylic alcohols in organic media. It is observed that the lipase immobilized on ceramic particles (PS-C Amano II) catalyzes the resolution in a highly enantioselective

  已开发出一种化学酶学方法，该方法是在水性介质中使用铟介导的杂环醛的烯丙基化烯丙基化，然后在有机介质中假单胞菌cepcia脂肪酶催化外消旋均烯丙基和均炔丙醇的对映选择性酰化。观察到，与天然酶（PS Amano）相比，固定在陶瓷颗粒上的脂肪酶（PS-C Amano II）以更少的时间以高对映选择性的方式催化拆分。该方法提供了新的功能化手性合成子，可用于合成天然和假天然产物。
• Mild and Efficient Allylation of Aldehydes by using Copper Fluorapatite as Catalyst
  作者：M. Lakshmi Kantam、G. T. Venkanna、K. B. Shiva Kumar、V. Balasubrahmanyam、G. Venkateswarlu、B. Sreedhar

  DOI：10.1002/adsc.200800159

  日期：2008.7.7

  A facile synthesis of homoallylic alcohols is achieved by the allylation of aldehydes with allylic metal reagents or allyl halides using copper fluorapatite (CuFAP) as catalyst under mild reaction conditions. A variety of aldehydes were converted to the corresponding homoallylic alchohols, demonstrating the versatility of the reaction.

  通过使用氟磷灰石铜（CuFAP）作为催化剂，在温和的反应条件下，将醛与烯丙基金属试剂或烯丙基卤化物进行烯丙基化，即可轻松合成均烯丙基醇。各种醛被转化为相应的均烯丙基醇，证明了该反应的多功能性。