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(2R,3R,3aS,7aS)-tetrahydro-3-hydroxy-2-phenyl-2H-furo[3,2-b]pyran-5(6H)-one | 158673-96-2

中文名称
——
中文别名
——
英文名称
(2R,3R,3aS,7aS)-tetrahydro-3-hydroxy-2-phenyl-2H-furo[3,2-b]pyran-5(6H)-one
英文别名
(+)-goniotharvesin;Goniotharvensin;(2R,3R,3aS,7aS)-3-hydroxy-2-phenyl-2,3,3a,6,7,7a-hexahydrofuro[3,2-b]pyran-5-one
(2R,3R,3aS,7aS)-tetrahydro-3-hydroxy-2-phenyl-2H-furo[3,2-b]pyran-5(6H)-one化学式
CAS
158673-96-2
化学式
C13H14O4
mdl
——
分子量
234.252
InChiKey
LKCVKUFQGOCQGT-WKSBVSIWSA-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

物化性质

  • 沸点:
    476.9±45.0 °C(Predicted)
  • 密度:
    1.298±0.06 g/cm3(Predicted)

计算性质

  • 辛醇/水分配系数(LogP):
    0.9
  • 重原子数:
    17
  • 可旋转键数:
    1
  • 环数:
    3.0
  • sp3杂化的碳原子比例:
    0.46
  • 拓扑面积:
    55.8
  • 氢给体数:
    1
  • 氢受体数:
    4

SDS

SDS:0e2eece98124202a6330077ea0330ec7
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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

点击查看最新优质反应信息

文献信息

  • Stereoselective Ring Expansion of Vinyl Oxiranes: Mechanistic Insights and Natural Product Total Synthesis
    作者:Matthew Brichacek、Lindsay A. Batory、Jon T. Njardarson
    DOI:10.1002/anie.200906830
    日期:2010.2.22
    applicable, catalytic, and stereoselective vinyl oxirane ring expansion is described (see scheme; hfacac=hexafluoroacetylacetonate). The stereoselectivity was influenced by several reaction parameters, and kinetic studies support a mechanistic proposal involving the in situ formation of a more reactive catalytic species. This ringexpansion reaction has been employed in the asymmetric total synthesis
    真是(紧张)的解脱!描述了第一个广泛适用的,催化的和立体选择性的乙烯基环氧乙烷环扩环(参见方案; hfacac =六氟乙酰丙酮酸酯)。立体选择性受几个反应参数的影响,动力学研究支持了一种机制性的提议,涉及原位形成更具反应性的催化物质。该扩环反应已用于(+)-邻苯二酚二醇的不对称全合成中。
  • The Effect of Sulfoxides on the Stereoselective Construction of Tetrahydrofurans: Total Synthesis of (+)-Goniothalesdiol
    作者:Gloria Hernández-Torres、M. Carmen Carreño、Antonio Urbano、Françoise Colobert
    DOI:10.1002/chem.201002637
    日期:2011.1.24
    Good to excellent stereoselectivities were achieved in the reductive cyclization (with Et3SiH/trimethylsilyl trifluoromethanesulfonate (TMSOTf)) of enantiopure hydroxy sulfinyl ketones en route to 2,5‐cis‐disubstituted tetrahydrofuran skeletons. Electrostatic effects of the exocyclic sulfoxide, which stabilized the reactive intermediate oxocarbenium conformations, were responsible for the observed
    对映体纯的羟基亚磺酰基酮在2,5-顺式-二取代的四氢呋喃骨架的还原环化反应中(用Et 3 SiH /三甲基甲硅烷三氟甲磺酸盐(TMSOTf))达到了良好的立体选择性。环外亚砜的静电作用使反应性中间体氧碳鎓构象稳定,这是观察到的立体控制的原因。提出了一个模型来解释结果。使用该反应和不对称还原β-酮亚砜作为关键步骤,促进了天然β-C-芳基糖苷(+)-goniothalesdiol的全部对映选择性合成。
  • Styryl-lactone derivatives and alkaloids from Goniothalamus borneensis (Annonaceae)
    作者:Shu-Geng Cao、Xiao-Hua Wu、Keng-Yeow Sim、B.K.H. Tan、J.T. Pereira、Swee-Hock Goh
    DOI:10.1016/s0040-4020(97)10422-7
    日期:1998.3
    Twelve natural products, including two new compounds, goniothalesdiol 1a and goniothalactam 2, were isolated from the bark of the Malaysian tree Goniothalamus borneensis (Annonaceae) and evaluated for their cytotoxic activity. Their structures were elucidated by spectroscopy including 2D-NMR spectroscopy. 1a, which was semisynthesised from (+)-goniothalenol (3a), was related to several cytotoxic styryl-lactones
    十二天然产品,包括两个新的化合物,goniothalesdiol 1A和goniothalactam 2,从马来西亚树的树皮中分离哥纳香属囊螺(番荔枝),并评价它们的细胞毒活性。通过包括2D-NMR光谱在内的光谱阐明了它们的结构。1a是由(+)-goniothalenol(3a)半合成的,与从该物种中分离出的几种具有细胞毒性的苯乙烯基内酯(4-8)有关。
  • Synthesis of (+)-goniothalesdiol and (+)-7-epi-goniothalesdiol
    作者:Matej Babjak、Peter Kapitán、Tibor Gracza
    DOI:10.1016/j.tet.2005.01.004
    日期:2005.2
    A total synthesis of (+)-goniothalesdiol, a 3,4-dihydroxy-2,5 -disubstituted tetrahydrofuran isolated from Goniothalamus borneensis (Annonaceae), and its 7-epimer is reported using oxycarbonylation methodology for construction of polyhydroxylated substituted heterocycles. Diastereoselectivity of addition of organometallic reagents to 2,3-O-isopropylidene-D-threose derivatives using theoretical calculations based on the semiempirical PM5 was studied. (C) 2005 Elsevier Ltd. All rights reserved.
  • Stereoselective Total Synthesis of Bioactive Styryllactones (+)-Goniofufurone, (+)7-<i>epi</i>-Goniofufurone, (+)-Goniopypyrone, (+)-Goniotriol, (+)-Altholactone, and (−)-Etharvensin
    作者:Kavirayani R. Prasad、Shivajirao L. Gholap
    DOI:10.1021/jo0702342
    日期:2008.1.1
    [GRAPHICS]Stereoselective total synthesis of biologically active styryllactones 7-epi-goniofufurone, goniofufurone, goniopypyrone, goniotriol, altholactone, and etharvensin was achieved in high overall yields from a common intermediate derived from D-(-)-tartaric acid. It is based on the utility of a masked tetrol, comprising an alkene tether and four contiguous hydroxy groups. The pivotal reaction sequence involves hydroxy-directed lactonization via the oxidation of alkene, and subsequent elaboration to styryllactones. The masked tetrol was prepared by the extension of gamma-phenyl-gamma-hydroxy butyramide, readily obtained from the bis-dimethylamide of tartaric acid, employing a combination of selective Grignard additions and a stereoselective reduction.
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同类化合物

马桑宁内酯 薁并[6,5-b]呋喃-2,4-二酮,十氢-5-(3-羟基丙氧基)-3a,4a-二甲基- 苦毒浆果[木防已属] 苦亭 艾瑞布林中间体 艾瑞布林 甲磺酸艾日布林 木防己苦毒宁 呋喃并[4,3,2-ij][2]苯并吡喃-2,7-二酮,2a,3,4,6,8a,8b-六氢-6-甲基-5-[(1S)-1,3,3-三甲基环己基]-,(2aR,6R,8aS,8bR)- 全内酯 二氢苦毒宁 6-甲基-4-氧代-4H-呋喃并[3,2-c]吡喃-3-甲酰氯 6-(4-羟基苯基)-2,3,3-三甲基-2H-呋喃并[5,4-b]吡喃-4-酮 4H-呋喃并[2,3-c]吡喃基莫匹罗星钠 3-甲基2H-呋喃并[2,3-c]吡喃-2-酮 3,5-二甲基2H-呋喃并[2,3-c]吡喃-2-酮 2H-呋喃并[2,3-c]吡喃-2-酮 2-[(1E,3E)-己-1,3-二烯基]-2,6-二甲基-5,6-二氢呋喃并[5,4-b]吡喃-3,4-二酮 (3aS,5S,6R,9E,14R,15R,15aR)-2,3,3a,4,5,6,7,8,11,12,13,14,15,15alpha-十四氢-6,10,14-三甲基-3-亚甲基-2-氧代-5,15-环氧环十四烷并[b]呋喃-6-醇乙酸酯 (3aR,4S,7aR)-4-羟基-3,3a,4,7a-四氢呋喃并[5,4-b]吡喃-2-酮 (3aα,3bβ,6aβ,7aα)-(+/-)-hexahydro-6-hydroxy-3a-(phenylmethyl)difuro<2,3-b:3',4'-d>furan-2(3H)-one (2R,3aS,4S,6S,7aR)-3a-benzyloxy-6-ethynyl-2-methoxy-4-p-methoxybenzyloxyhexahydrofuro[2,3-b]pyran (1R,2S,6S,7S)-5,6-Dimethoxy-8-oxo-3,9-dioxa-tricyclo[5.2.2.02,6]undeca-4,10-diene-10-carboxylic acid methyl ester N3,5'-Cyclo-2',3'-O-isopropyliden-8-oxyguanosin (3aR,4aR,7aS,8aS)-2-Thioxo-hexahydro-furo[3',4':4,5]benzo[1,2-d][1,3]dioxol-5-one 9-(3',5'-O-Isopropyliden-2-keto-β-D-xylofuranosyl)-adenin (1aR,1bS,4aS,5aS)-1a-Isopropyl-hexahydro-1,4-dioxa-cyclopropa[a]pentalen-3-one [(3aR,4S,6R,7S,7aR)-7-acetyloxy-2-oxo-4-phenylsulfanyl-3,3a,4,6,7,7a-hexahydropyrano[3,4-d][1,3]oxazol-6-yl]methyl acetate (2R,3R,3aS,6R,7R,7aR)-7-azido-6-methoxy-2-phenylsulfanyl-hexahydrofuro[3,2-b]pyran-3-ol 7-Dihydroxymethyl-O1,O2-isopropyliden-3,7-anhydro-6-desoxy-D-glucofuranose (1S,2S,6S,7R)-5,6-Dimethoxy-8-oxo-3,9-dioxa-tricyclo[5.2.2.02,6]undeca-4,10-diene-10-carboxylic acid methyl ester (2R,3S)-2-Methyl-4-oxo-oxetane-3-carboxylic acid (1R,5S)-6-methylene-3-oxo-bicyclo[3.2.1]oct-1-ylmethyl ester 3-C-(3,4,6-tri-O-acetyl-2-deoxy-2-tetrachlorophthalimido-β-D-glucopyranosyl)-1-propene (2R,4aR,5aS,8aS,9S,9aR)-5a-methoxy-7-oxo-2-phenyloctahydrofuro[2',3':5,6]pyrano[3,2-d][1,3]dioxin-9-yl acetate (4R,5E,7R,9S,10S,11E,14S)-9-((benzyloxy)methoxy)-4,10-bis((tert-butyldimethylsilyl)oxy)-7-(dimethoxymethyl)-14-(furan-3-yl)-6,12-dimethyloxacyclotetradeca-5,11-dien-2-one 3-Furan-3-yl-8-methyl-5-(4,5,6,7-tetrahydro-isobenzofuran-4-yl)-2,7-dioxa-bicyclo[3.2.1]octane methyl 2,3"-anhydro-4,6-O-benzylidene-3-C-[2,2-dihydroxyethyl]-α-D-glucopyranoside (3aR,5S,6S,7aR)-5-((R)-but-3-en-2-yl)-6-hydroxyhexahydro-2H-furo[3,2-b]pyran-2-one 7-(3-Furan-3-yl-8-methyl-2,7-dioxa-bicyclo[3.2.1]oct-5-yl)-1,3,4,5,6,7-hexahydro-isobenzofuran-1-ol