(Z)-4-methoxybut-2-en-1-ol | 30339-05-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (Z)-4-methoxybut-2-en-1-ol
• CAS: 30339-05-0
• 化学式: C₅H₁₀O₂
• 分子量: 102.133
• InChiKey: JWAVFTBBSAZCCU-IHWYPQMZSA-N

物化性质

• 沸点：
  80-83 °C(Press: 5 Torr)
• 密度：
  0.940±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  7
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z)-4-methoxybut-2-en-1-ol 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以52%的产率得到(E)-4-甲氧基丁烯醛
  参考文献：
  名称：

  Copyrine alkaloids: synthesis, spectroscopic characterization, and antimycotic/antimycobacterial activity of A- and B-ring-functionalized sampangines

  摘要：

  Several A- and B-ring-substituted sampangines were synthesized and evaluated for antifungal and antimycobacterial activity against AIDS-related opportunistic infection pathogens. Electrophilic halogenation provided a channel for structural elaboration of the sampangine B-ring at position 4, while the synthesis of A-ring 3-substituted sampangines and benzo[4,5]sampangine (24) were achieved from the corresponding functionalized cleistopholines. Two-dimensional NMR spectroscopy was used to rigorously characterize the A- and B-ring substituent patterns. Structure-activity relationship studies revealed the activity of the sampangines was enhanced by the presence of a substituent at position 3 or by a 4,5-benzo group.

  DOI：

  10.1021/jm00100a012
• 作为产物：
  描述：

  顺式-1,2-二羟甲基乙烯 、 碘甲烷 在 sodium hydride 作用下， 生成 (Z)-4-methoxybut-2-en-1-ol
  参考文献：
  名称：

  Highly Stereoselective Chelation-Controlled Allylation and Deuteration ofα-Chiralα,α′-Dialkoxy Radicals

  摘要：

  当在路易斯酸（MgBr2·OEt2用于烯丙基化；MgI2用于氘化）存在下进行反应时，β-手性β-烷氧基-α-溴代醛二甲缩醛和重排烷氧基溴化物的自由基介导的烯丙基化和氘化反应中的立体选择性显著增强。

  DOI：

  10.1246/cl.1996.845

文献信息

• Nickel-Catalyzed Enantioselective Synthesis of Pre-Differentiated Homoallylic <i>syn</i>- or <i>anti</i>-1,2-Diols from Aldehydes and Dienol Ethers
  作者：Thomas Q. Davies、John J. Murphy、Maxime Dousset、Alois Fürstner

  DOI：10.1021/jacs.1c07042

  日期：2021.9.1

  Nickel catalysis allied with cyclodiphosphazane or VAPOL-derived phosphoramidite ligands provides selective access to monoprotected vicinal diols by reductive coupling of dienol ethers and aldehydes. The observed regioselectivity is unprecedented, in that the diene reacts at the least nucleophilic and most hindered C atom that is attached to the oxygen substituent rather than at the terminal position

  镍催化与环二磷氮烷或 VAPOL 衍生的亚磷酰胺配体结合，通过二烯醇醚和醛的还原偶联提供对单保护的邻二醇的选择性访问。观察到的区域选择性是前所未有的，因为二烯在亲核性最低且受阻最大的 C 原子上反应，该 C 原子连接到氧取代基而不是在末端位置。值得注意的是，产品的顺式和反式非对映异构体都可以根据二烯伙伴的配置获得，通常具有出色的非对映选择性和对映选择性。
• Brønsted acid catalyzed regioselective aza-Ferrier reaction: a novel synthetic method for α-(N-Boc-2-pyrrolidinyl) aldehydes
  作者：Eiji Tayama、Seijun Otoyama、Wataru Isaka

  DOI：10.1039/b806492j

  日期：——

  The 1,4-elimination reaction of (Z)-N-Boc-2-(4-methoxy-2-alkenyloxy)pyrrolidines (1) is shown to proceed with high (1E,3E)-stereoselectivity to afford N-Boc-2-(1,3-dienyloxy)pyrrolidines (2); the Brønsted acid catalyzed aza-Ferrier reaction of the N-Boc-2-(1,3-dienyloxy)pyrrolidines (2) provides α-(N-Boc-2-pyrrolidinyl) aldehydes (3) in excellent yields with high α-regioselectivities.

  (Z)-N-Boc-2-(4-甲氧基-2-烯丙氧基)吡咯烷（1）的1,4-消除反应表现出高度的（1E,3E）-立体选择性，生成N-Boc-2-(1,3-二烯氧基)吡咯烷（2）；布朗斯特酸催化的N-Boc-2-(1,3-二烯氧基)吡咯烷（2）的氮杂-费里尔反应在优异的产率下提供了具有高α-区域选择性的α-(N-Boc-2-吡咯烷基)醛（3）。
• Compounds and compositions useful as antifungal and antimycobacterial
  申请人：The University of Mississippi

  公开号：US05227383A1

  公开（公告）日：1993-07-13

  New analogs of sampangine and cleistopholine, compositions and methods of preparation thereof, method of treating fungal and mycobacterial infections. The compounds have the general formula: ##STR1## where the R.sub.1, R.sub.2, and R.sub.5 groups are defined herein.

  新的sampangine和cleistopholine的类似物，其组成物和制备方法，治疗真菌和分枝杆菌感染的方法。这些化合物具有一般公式：##STR1##其中R.sub.1、R.sub.2和R.sub.5基团在此处被定义。
• Expanding the Scope of Biomass-Derived Chemicals through Tandem Reactions Based on Oxorhenium-Catalyzed Deoxydehydration
  作者：Mika Shiramizu、F. Dean Toste

  DOI：10.1002/anie.201307564

  日期：2013.12.2

  New modes of DODH: Oxorhenium compounds act as deoxydehydration(DODH)/acid dual‐purpose catalysts to transform biomass‐derived diol substrates into a variety of commodity chemical precursors. The power of this approach is highlighted by a tandem [1,3]‐OH shift/DODH of 2‐ene‐1,4‐diols and 2,4‐diene‐1,6‐diols, and by a DODH/esterification sequence of sugar acids to unsaturated esters for the production

  DODH的新模式：氧化hen化合物充当脱氧脱水（DODH）/酸两用催化剂，将生物质衍生的二醇底物转化为多种商品化学前体。通过2-烯-1,4-二醇和2,4-二烯-1,6-二醇的串联[1,3] -OH移位/ DODH以及DODH /酯化序列突出了这种方法的优势糖酸到不饱和酯的合成，用于生产聚合物和增塑剂。
• [EN] ASPARTYL PROTEASE INHIBITORS<br/>[FR] INHIBITEURS D'ASPARTYL PROTÉASE
  申请人：MEDIVIR AB

  公开号：WO2010107384A1

  公开（公告）日：2010-09-23

  A compound of formula (I) N-oxides, addition salts, quaternary amines metal complexes stereochemically isomeric forms and metabolites thereof, wherein A is CR1 Or N; formula (A) or formula (B) D is H, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, G is NR10 or O Q is C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6Cycloalkyl, aryl or heterocyclyl; W is H, C1-C6alkyl, C3-C6Cycloalkyl, CH2F, CHF2 or CF3; one of X' and X" is H or CH3, the other is C1-C3alkyl, F, OH, NRaRb, CF3 or N3; or X' and X" are both F; Y is NRd or O; Z is O, NRa, CHRd, CF2 or S(=0)r or a bond; the other variables are as defined in the specification. The compounds of the invention are inhibitors of BACE and are among other things useful for the treatment and/or prevention of conditions associated with BACE activity such as Alzheimer's disease.

  公式（I）的化合物N-氧化物，加成盐，季铵盐金属配合物立体化异构体及其代谢物，其中A为CR1或N；公式（A）或公式（B）D为H，C1-C6烷基，C2-C6烯基，C2-C6炔基，G为NR10或O，Q为C1-C6烷基，C2-C6烯基，C2-C6炔基，C3-C6环烷基，芳基或杂环烷基；W为H，C1-C6烷基，C3-C6环烷基，CH2F，CHF2或CF3；X'和X"中的一个为H或CH3，另一个为C1-C3烷基，F，OH，NRaRb，CF3或N3；或者X'和X"都是F；Y为NRd或O；Z为O，NRa，CHRd，CF2或S（=0）r或键；其他变量如规范中定义。本发明的化合物是BACE的抑制剂，除其他用途外，还可用于治疗和/或预防与BACE活性相关的疾病，如阿尔茨海默病。