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(2R,4R)-2-(benzyloxy)-4-pentanol | 124338-54-1

中文名称
——
中文别名
——
英文名称
(2R,4R)-2-(benzyloxy)-4-pentanol
英文别名
(2R,4R)-2-(benzyloxy)pentan-4-ol;(2R,4R)-4-benzyloxy-2-pentanol;(2R,4R)-4-phenylmethoxypentan-2-ol
(2R,4R)-2-(benzyloxy)-4-pentanol化学式
CAS
124338-54-1
化学式
C12H18O2
mdl
——
分子量
194.274
InChiKey
ZDGYZKNTFSWSEU-GHMZBOCLSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    2.1
  • 重原子数:
    14
  • 可旋转键数:
    5
  • 环数:
    1.0
  • sp3杂化的碳原子比例:
    0.5
  • 拓扑面积:
    29.5
  • 氢给体数:
    1
  • 氢受体数:
    2

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量
  • 下游产品
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为反应物:
    描述:
    (2R,4R)-2-(benzyloxy)-4-pentanol三氟甲磺酸三甲基硅酯三乙胺 作用下, 以 四氢呋喃二氯甲烷 为溶剂, 反应 30.0h, 生成 (1'R,3'R)-1,1-bis<3'-(benzyloxy)-1'-methylbutoxy>heptane
    参考文献:
    名称:
    Studies on the mechanism and origin of stereoselective opening of chiral dioxane acetals
    摘要:
    A systematic examination of the mechanism and origin of stereoselection in the reaction of dioxane acetals with allyltrimethylsilane was undertaken. Experimental tests for two limiting mechanisms, synchronous (S(N)2-like) and dissociative (S(N)1-like) substitution processes, were investigated. The meso 2,4,6-trisubstituted 1,3-dioxane acetals cis- and trans-1 provided an interesting opportunity to test the timing of bond breaking and making in the substitution reaction. The modest and C(2)-substituent-dependent selectivity excluded the possibility of a direct S(N)2-type attack on a complexed acetal. Further, the enol ethers 3 and 5 and acyclic acetal 7 were studied as precursors of the putative oxocarbenium ion intermediate in the dissociative limit. The weak and inverted selectivity observed with these substrates ruled out the intermediacy of the extended, separated ion in reactions of the cyclic acetals under similar conditions. A unified mechanistic scheme involving three distinct ion pairs is proposed to explain the dependence of allylation selectivity on structural and experimental variables. The three species are analogous to those proposed in the classic Winstein scheme: (1) an intimate ion pair, (2) an external ion pair, and (3) a separated ion. Each of these proposed intermediates has a different stereochemical profile and the ultimate outcome is a composite of those factors that balance the contribution of the different intermediates. The influence of C(2) substituent, acetal configuration, Lewis acid type and stoichiometry, allylsilane stoichiometry, concentration, solvent, and temperature were investigated and integrated in the proposed mechanistic scheme.
    DOI:
    10.1021/ja00021a040
  • 作为产物:
    描述:
    苯甲醛二异丁基氢化铝对甲苯磺酸 作用下, 以 二氯甲烷甲苯 为溶剂, 反应 12.5h, 生成 (2R,4R)-2-(benzyloxy)-4-pentanol
    参考文献:
    名称:
    Studies on the mechanism and origin of stereoselective opening of chiral dioxane acetals
    摘要:
    A systematic examination of the mechanism and origin of stereoselection in the reaction of dioxane acetals with allyltrimethylsilane was undertaken. Experimental tests for two limiting mechanisms, synchronous (S(N)2-like) and dissociative (S(N)1-like) substitution processes, were investigated. The meso 2,4,6-trisubstituted 1,3-dioxane acetals cis- and trans-1 provided an interesting opportunity to test the timing of bond breaking and making in the substitution reaction. The modest and C(2)-substituent-dependent selectivity excluded the possibility of a direct S(N)2-type attack on a complexed acetal. Further, the enol ethers 3 and 5 and acyclic acetal 7 were studied as precursors of the putative oxocarbenium ion intermediate in the dissociative limit. The weak and inverted selectivity observed with these substrates ruled out the intermediacy of the extended, separated ion in reactions of the cyclic acetals under similar conditions. A unified mechanistic scheme involving three distinct ion pairs is proposed to explain the dependence of allylation selectivity on structural and experimental variables. The three species are analogous to those proposed in the classic Winstein scheme: (1) an intimate ion pair, (2) an external ion pair, and (3) a separated ion. Each of these proposed intermediates has a different stereochemical profile and the ultimate outcome is a composite of those factors that balance the contribution of the different intermediates. The influence of C(2) substituent, acetal configuration, Lewis acid type and stoichiometry, allylsilane stoichiometry, concentration, solvent, and temperature were investigated and integrated in the proposed mechanistic scheme.
    DOI:
    10.1021/ja00021a040
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文献信息

  • Intramolecular OH⋅⋅⋅Fluorine Hydrogen Bonding in Saturated, Acyclic Fluorohydrins: The γ-Fluoropropanol Motif
    作者:Bruno Linclau、Florent Peron、Elena Bogdan、Neil Wells、Zhong Wang、Guillaume Compain、Clement Q. Fontenelle、Nicolas Galland、Jean-Yves Le Questel、Jérôme Graton
    DOI:10.1002/chem.201503253
    日期:2015.12.1
    is commonly exercised in compound property optimization. However, the influence of fluorination on hydrogenbond (HB) properties of adjacent functional groups, as well as the HB‐accepting capacity of fluorine itself, is still not completely understood. Although the formation of OH⋅⋅⋅F intramolecular HBs (IMHBs) has been established for conformationally restricted fluorohydrins, such interaction in
    氟化通常用于化合物性能优化。然而,氟化对相邻官能团氢键(HB)性质以及氟本身的HB接受能力的影响尚不完全清楚。尽管构象限制的氟代醇可以形成 OH⋅⋅⋅F 分子内 HBs (IMHBs),但柔性化合物中的这种相互作用仍然存在疑问。与之前的报道相比,本文首次证明了无环饱和 γ-氟代醇中存在 OH⋅⋅⋅F IMHB,甚至对于母体 3-氟丙-1-醇也是如此。相对立体化学对相应的h1 J OH⋅⋅⋅F值具有至关重要的影响,如syn ‐ 和anti- 4-氟戊烷-2-ol (6.6 和 1.9 Hz) 所示。OH⋅⋅⋅F IMHBs 的大小及其对整体分子构象、氟化基序和烷基取代水平的强烈依赖性,通过量子化学计算得到了合理化。对于给定的烷基链,“屏蔽规则”适用于 OH⋅⋅⋅F IMHB 能量。令人惊讶的是,预测的 OH⋅⋅⋅F IMHB 能量仅比相应的 OH⋅⋅⋅OMe 弱一些。这些结果为脂肪醇氟化的影
  • Conformer Equilibria in 2,4-Disubstituted Pentane Derivatives
    作者:Reinhard W. Hoffmann、Dirk Stenkamp、Thomas Trieselmann、Richard Göttlich
    DOI:10.1002/(sici)1099-0690(199911)1999:11<2915::aid-ejoc2915>3.0.co;2-r
    日期:1999.11
    only two conformations. Substituents have been varied in order to find those which lead to a strong preference of the conformer equilibrium. Studying 2-substituted 4-methylpentanes 3 and 4-benzyloxypentanes 12, it has been shown that substituent effects on the conformer equilibria are not additive, as would be expected on the grounds of steric effects alone. Rather, interactions between polar groups
    2,4-二取代戊烷是基本上仅采用两种构象的分子。为了找到导致构象异构体平衡的强烈偏好的取代基,已经改变了取代基。研究 2-取代的 4-甲基戊烷 3 和 4-苄氧基戊烷 12,已经表明取代基对构象异构体平衡的影响不是相加的,正如仅基于空间效应所预期的那样。相反,极性基团之间的相互作用加强了构象异构体平衡的偏差。当应用于 2,4-二取代戊烷时,氯或邻苯二甲酰亚胺等取代基将构象异构体平衡移动到 gg 构象异构体一侧,优先级超过 90%。
  • Stereoselective Synthesis and Reactions of Secondary Alkyllithium Reagents Functionalized at the 3-Position
    作者:Kohei Moriya、Dorian Didier、Meike Simon、Jeffrey M. Hammann、Guillaume Berionni、Konstantin Karaghiosoff、Hendrik Zipse、Herbert Mayr、Paul Knochel
    DOI:10.1002/anie.201409165
    日期:2015.2.23
    Secondary alkyllithium reagents bearing an OTBS group (TBS=tert‐butyldimethylsilyl) at the 3‐position can be prepared stereoconvergently through an I/Li exchange from a diastereomeric mixture of the corresponding secondary alkyl iodides. These lithium reagents react with a range of electrophiles, including carbon electrophiles, with retention of configuration to yield various 1,3‐difunctionalized derivatives
    可以通过I / Li交换从相应的仲烷基碘化物的非对映异构体混合物中立体聚合制备在3位带有OTBS基团(TBS =叔丁基二甲基甲硅烷基)的仲烷基锂试剂。这些锂试剂可与多种亲电试剂(包括碳亲电试剂)反应,并保留构型,以产生具有良好非对映选择性的各种1,3-双官能化衍生物。动力学研究表明,3-甲硅烷氧基可大大加速锂取代的碳原子上的差向异构。该方法为构建具有出色立体选择性的手性开链分子提供了新途径。
  • A Highly Regio- and Chemoselective Reductive Cleavage of Benzylidene Acetals with EtAlCl<sub>2</sub>-Et<sub>3</sub>SiH
    作者:Sundarababu Baskaran、Vijayakrishnan Balakumar、Appu Aravind
    DOI:10.1055/s-2004-817752
    日期:——
    A highly regio- and chemoselective reductive cleavage of benzylidene acetals derived from 1,2- and 1,3-diols was achieved under mild conditions using EtAlCl2-Et3SiH reagent system in good to excellent yields. Labile protecting groups such as N-Boc, N-Cbz and -OTBDMS are found to be stable under the reaction conditions.
    在温和的条件下,使用 EtAlCl2-Et3SiH 试剂体系实现了对源自 1,2- 和 1,3- 二醇的亚苄基乙缩醛的高区域和化学选择性还原裂解,并获得了良好甚至优异的产率。在反应条件下,N-叔丁氧羰基、N-苄氧羰基和 -OTBDMS 等易变保护基团都很稳定。
  • Unusual p-Coumarates from the Stems of Vaccinium myrtillus
    作者:Simona Hybelbauerová、Jan Sejbal、Martin Dračínský、Iva Rudovská、Bohumír Koutek
    DOI:10.1002/hlca.200900220
    日期:2009.12
    pentane‐2,4‐diol and p‐coumaric acid (=3‐(4‐hydroxyphenyl)prop‐2‐enoic acid) along with 13 known compounds including 6 oleanane‐ and ursane‐type triterpenoids were isolated from MeOH extracts of the stems of Vaccinium myrtillus. The structures of the new compounds were assigned as (2S,4R)‐4‐(β‐D‐glucopyranosyloxy)pentan‐2‐yl (2E)‐p‐coumarate (1) and its aglycone 2 on the basis of 1D‐ and 2D‐NMR spectroscopic
    戊烷-2,4-二醇和对-香豆酸(= 3-(4-羟苯基)丙-2-烯酸)的两种先前未报告的酯1和2以及13种已知化合物,包括6种齐墩果烷和烷型从牛痘越桔茎的MeOH提取物中分离出三萜类化合物。新化合物的结构被指定为(2 S,4 R)‐4‐(β ‐ D‐吡喃葡萄糖基氧基)戊二-2-基(2E)‐对香豆酸酯(1)及其糖苷配基2基于分离和合成的化合物的1D和2D-NMR光谱分析以及分子建模实验。这是关于天然产物中苯酚衍生的酸与糖苷部分之间存在手性戊烷-2,4-二醇连接基的首次报道。
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