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1,1-二甲基铟烷-5,6-二醇 | 5989-16-2

中文名称
1,1-二甲基铟烷-5,6-二醇
中文别名
墨沙酮
英文名称
maesopsin
英文别名
2,4,6-trihydroxy-2-[(4-hydroxyphenyl)methyl]-1-benzofuran-3-one
1,1-二甲基铟烷-5,6-二醇化学式
CAS
5989-16-2
化学式
C15H12O6
mdl
——
分子量
288.257
InChiKey
LOFYFDPXORJJEE-UHFFFAOYSA-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

  • 熔点:
    218-220 °C
  • 沸点:
    620.0±55.0 °C(Predicted)
  • 密度:
    1.646±0.06 g/cm3(Predicted)

计算性质

  • 辛醇/水分配系数(LogP):
    2.2
  • 重原子数:
    21
  • 可旋转键数:
    2
  • 环数:
    3.0
  • sp3杂化的碳原子比例:
    0.13
  • 拓扑面积:
    107
  • 氢给体数:
    4
  • 氢受体数:
    6

安全信息

  • WGK Germany:
    3

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

反应信息

点击查看最新优质反应信息

文献信息

  • [EN] SYNTHESIS OF C-3 COUPLED BIFLAVONOIDS AND C-3 COUPLED BIFLAVONOID ANALOGUES<br/>[FR] SYNTHÈSE DE BIFLAVONOÏDES COUPLÉS EN C-3 ET D'ANALOGUES DE BIFLAVONOÏDES COUPLÉS EN C-3
    申请人:UNIV FREE STATE ZA
    公开号:WO2011021167A1
    公开(公告)日:2011-02-24
    The invention relates to methods for the preparation of an optically inactive and optically active compounds which are selected from the group consisting of C-3 coupled biflavonoids and C-3 coupled biflavonoid analogues from a starting material or intermediate which are respectively selected from the group consisting of optically inactive or optically active flavan-3-ols and optically active flavan-3-ones, the method comprising the steps of (a) providing an optically inactive or active compound having a fIavan-3-ol structure or a compound which is a flavan-3-one, (b) if a compound having a flavan-3-ol structure with a hydroxy group on the C-3 carbon is selected as starting material, converting the hydroxy group on the C-3 carbon of the compound having the flavan-3-ol structure to an oxo group to form a flavan-3-one of that compound, (c) providing a compound having a nucleophilic aromatic moiety, which compound is selected from the group of compounds having a nucleophilic aromatic moiety and which have flavonoid base structures and compounds having a nucleophilic aromatic moiety and which do not have a flavonoid base structure, (d) contacting the flavan-3-one provided by step (a) or obtained by step (b) with the compound containing the nucleophilic aromatic moiety in the presence of a Lewis acid; (e) forming a first intermediate compound wherein the oxo group on the C-3 carbon is converted to a hydroxy group by virtue of nucleophilic addition when the compound containing the nucleophilic aromatic moiety is contacted to the C-3 carbon of the flavan-3-one, (f) subjecting the first intermediate compound to dehydration so as to introduce a double bond between the C-3 carbon and C-4 carbon of the intermediate compound with the concomitant removal of the hydroxy group from the C-3 carbon to form an optically active flavene compound which is substituted by the nucleophilic aromatic moiety on the C-3 carbon, (g) optionally subjecting the resultant flavene compound to hydroboration-oxidation hydration thereby removing said double bond between the C-3 carbon and the C-4 carbon with the concomitant introduction of a hydroxy group at the C-4 carbon to form a second intermediate compound, (h) further optionally oxidizing the second intermediate compound of step (g) thereby converting the hydroxy group at the said C-4 carbon to an oxo group, thereby forming a biflavonoid or biflavonoid analogue which is substituted by the selected nucleophilic aromatic moiety on the C-3 carbon, (ι) further optionally, and alternatively to step (h), subjecting the resultant flavene compound of step (f) to OsC4 dihydroxylation thereby removing said double bond between the C-3 carbon and C-4 carbon with the concomitant introduction of a hydroxy group at the C-4 carbon and a hydroxy group at the C-3 carbon to form a third intermediate compound, and (j) subjecting the third intermediate compound to dehydration whereby the hydroxy group at the C-3 carbon is removed and a double bond is introduced between the C-3 carbon and C-4 carbon thereby forming an enol product and allowing such enol product to rearrange spontaneously to form a biflavonoid or biflavonoid analogue having an oxo group at its C-4 carbon and which is substituted by the selected nucleophilic aromatic moiety on its C-3 carbon.
    该发明涉及从起始物质或中间体中选择的光学不活性和光学活性化合物的制备方法,所述化合物选自C-3偶联的双黄酮类和C-3偶联的双黄酮类类似物,所述起始物质或中间体分别选自光学不活性或光学活性的黄酮-3-醇和光学活性的黄酮-3-酮,所述方法包括以下步骤:(a)提供具有黄酮-3-醇结构或为黄酮-3-酮的化合物,该化合物是光学不活性或活性的;(b)如果选择具有C-3碳上羟基的黄酮-3-醇结构的化合物作为起始物质,则将该具有黄酮-3-醇结构的化合物上的C-3碳上的羟基转化为醛基,形成该化合物的黄酮-3-酮;(c)提供具有亲核芳香基团的化合物,所述化合物选自具有亲核芳香基团的化合物和具有黄酮基本结构的化合物以及具有亲核芳香基团的化合物和不具有黄酮基本结构的化合物;(d)在存在Lewis酸的情况下,将步骤(a)提供的或步骤(b)获得的黄酮-3-酮与含有亲核芳香基团的化合物接触;(e)形成第一中间化合物,其中通过亲核加成使含有亲核芳香基团的化合物与黄酮-3-酮的C-3碳接触时,C-3碳上的醛基转化为羟基;(f)将第一中间化合物脱,以在中间化合物的C-3碳和C-4碳之间引入双键,并同时去除C-3碳上的羟基,形成一种在C-3碳上由亲核芳香基团取代的光学活性黄烯化合物;(g)可选地将所得的黄烯化合物经过氢氧化合反应,从而去除C-3碳和C-4碳之间的双键,并同时在C-4碳引入羟基,形成第二中间化合物;(h)可选地进一步氧化步骤(g)中的第二中间化合物,从而将C-4碳上的羟基转化为醛基,形成在C-3碳上由选定的亲核芳香基团取代的双黄酮或双黄酮类似物;(ι)可选地,作为步骤(h)的替代,将步骤(f)中的所得黄烯化合物经过OsC4双羟基化反应,从而去除C-3碳和C-4碳之间的双键,并同时在C-4碳和C-3碳引入羟基,形成第三中间化合物;(j)将第三中间化合物脱,从而去除C-3碳上的羟基,并在C-3碳和C-4碳之间引入双键,形成烯醇产物,并使该烯醇产物自发重排,形成在其C-4碳上具有醛基且在其C-3碳上由选定的亲核芳香基团取代的双黄酮或双黄酮类似物。
  • Synthesis of C-3 Coupled Biflavonoids and C-3 Coupled Biflavonoid Analogues
    申请人:Van Der Westhuizen Jan Hendrik
    公开号:US20120289715A1
    公开(公告)日:2012-11-15
    The invention relates to methods for the preparation of an optically inactive and optically active compounds which are selected from the group consisting of C-3 coupled biflavonoids and C-3 coupled biflavonoid analogues from a starting material or intermediate which are respectively selected from the group consisting of optically inactive or optically active flavan-3-ols and optically active flavan-3-ones, the method comprising the steps of (a) providing an optically inactive or active compound having a flavan-3-ol structure or a compound which is a flavan-3-one, (b) if a compound having a flavan-3-ol structure with a hydroxy group on the C-3 carbon is selected as starting material, converting the hydroxy group on the C-3 carbon of the compound having the flavan-3-ol structure to an oxo group to form a flavan-3-one of that compound, (c) providing a compound having a nucleophilic aromatic moiety, which compound is selected from the group of compounds having a nucleophilic aromatic moiety and which have flavonoid base structures and compounds having a nucleophilic aromatic moiety and which do not have a flavonoid base structure, (d) contacting the flavan-3-one provided by step (a) or obtained by step (b) with the compound containing the nucleophilic aromatic moiety in the presence of a Lewis acid; (e) forming a first intermediate compound wherein the oxo group on the C-3 carbon is converted to a hydroxy group by virtue of nucleophilic addition when the compound containing the nucleophilic aromatic moiety is contacted to the C-3 carbon of the flavan-3-one, (f) subjecting the first intermediate compound to dehydration so as to introduce a double bond between the C-3 carbon and C-4 carbon of the intermediate compound with the concomitant removal of the hydroxy group from the C-3 carbon to form an optically active flavene compound which is substituted by the nucleophilic aromatic moiety on the C-3 carbon, (g) optionally subjecting the resultant flavene compound to hydroboration-oxidation hydration thereby removing said double bond between the C-3 carbon and the C-4 carbon with the concomitant introduction of a hydroxy group at the C-4 carbon to form a second intermediate compound, (h) further optionally oxidizing the second intermediate compound of step (g) thereby converting the hydroxy group at the said C-4 carbon to an oxo group, thereby forming a biflavonoid or biflavonoid analogue which is substituted by the selected nucleophilic aromatic moiety on the C-3 carbon, (i) further optionally, and alternatively to step (h), subjecting the resultant flavene compound of step (f) to OsO 4 dihydroxylation thereby removing said double bond between the C-3 carbon and C-4 carbon with the concomitant introduction of a hydroxy group at the C-4 carbon and a hydroxy group at the C-3 carbon to form a third intermediate compound, and (j) subjecting the third intermediate compound to dehydration whereby the hydroxy group at the C-3 carbon is removed and a double bond is introduced between the C-3 carbon and C-4 carbon thereby forming an enol product and allowing such enol product to rearrange spontaneously to form a biflavonoid or biflavonoid analogue having an oxo group at its C-4 carbon and which is substituted by the selected nucleophilic aromatic moiety on its C-3 carbon.
    该发明涉及一种从起始物质或中间体中选择的光学不活性和光学活性化合物的制备方法,所述化合物选自C-3偶联的双黄酮类化合物和C-3偶联的双黄酮类似物,所述起始物质或中间体分别选自光学不活性或光学活性的黄酮-3-醇和光学活性的黄酮-3-酮,所述方法包括以下步骤:(a)提供具有黄酮-3-醇结构或为黄酮-3-酮的化合物,该化合物是光学不活性或活性的;(b)如果选择具有C-3碳上羟基的黄酮-3-醇结构化合物作为起始物质,则将具有黄酮-3-醇结构的化合物的C-3碳上的羟基转化为羟基,形成该化合物的黄酮-3-酮;(c)提供具有亲核芳香基团的化合物,所述化合物选自具有亲核芳香基团的化合物和具有黄酮类基本结构的化合物以及具有亲核芳香基团的化合物和不具有黄酮类基本结构的化合物;(d)在存在Lewis酸的情况下,将步骤(a)提供或步骤(b)获得的黄酮-3-酮与含有亲核芳香基团的化合物接触;(e)形成第一中间化合物,其中通过亲核加成使含有亲核芳香基团的化合物与黄酮-3-酮的C-3碳接触时,C-3碳上的羟基转化为羟基;(f)将第一中间化合物脱,以在中间化合物的C-3碳和C-4碳之间引入双键,并同时去除C-3碳上的羟基,形成由亲核芳香基团取代C-3碳上的光学活性黄烯化合物;(g)可选地将所得的黄烯化合物经过氢氧化合反应,从而去除C-3碳和C-4碳之间的双键,并同时在C-4碳引入羟基,形成第二中间化合物;(h)可选地进一步氧化步骤(g)中的第二中间化合物,将C-4碳上的羟基转化为羟基,从而形成在C-3碳上由所选亲核芳香基团取代的双黄酮或双黄酮类似物;(i)可选地,作为步骤(h)的替代,将步骤(f)中的所得黄烯化合物经过OsO4二羟基化反应,从而去除C-3碳和C-4碳之间的双键,并同时在C-4碳和C-3碳引入羟基,形成第三中间化合物;(j)将第三中间化合物脱,从而去除C-3碳上的羟基,并在C-3碳和C-4碳之间引入双键,从而形成烯醇产物,并使该烯醇产物自发重排,形成在其C-4碳上具有羟基的双黄酮或双黄酮类似物,并在其C-3碳上由所选亲核芳香基团取代。
  • Composition comprising cannabinoids for relief of pain
    申请人:CANOPY HEALTH INNOVATIONS
    公开号:US11110069B2
    公开(公告)日:2021-09-07
    The present technology generally relates to compositions comprising cannabinoids for relieving pain in a subject and to methods of using such compositions for relieving pain in a subject.
    本技术一般涉及用于缓解受试者疼痛的包含大麻素的组合物,以及使用此类组合物缓解受试者疼痛的方法。
  • SYNTHESIS OF C-3 COUPLED BIFLAVONOIDS AND C-3 COUPLED BIFLAVONOID ANALOGUES
    申请人:University Of The Free State
    公开号:EP2467369A1
    公开(公告)日:2012-06-27
  • COMPOSITIONS COMPRISING CANNABIDIOL, TETRAHYDROCANNABINOL, TERPENES, AND FLAVONOIDS AND USE THEREOF IN THE TREATMENT OF INSOMNIA
    申请人:Canopy Health Innovations
    公开号:EP3687527A1
    公开(公告)日:2020-08-05
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同类化合物

降钙素 金色草素 苦杏碱醇B 海生菊甙 噢弄斯定 E-2-[(4-甲氧基苯基)亚甲基]苯并[b]呋喃-3-酮 6-羟基-2-[羟基-(4-羟基苯基)甲基]-1-苯并呋喃-3-酮 6,4''-二羟基橙酮 5-乙酰基-2-苯甲酰基-1-苯并呋喃-3-酮 4-甲氧基-2-亚胡椒基-苯并呋喃-3-酮 3(2H)-苯并呋喃酮,4,6-二羟基-2-[(4-羟基苯基)亚甲基]-,(2Z)- 3',5'-二溴-2',4,4',6-四羟基橙酮 2-苯甲酰基-6-甲氧基-1-苯并呋喃-3-酮 2-苯甲酰基-5-甲基-1-苯并呋喃-3-酮 2-苯甲酰基-1-苯并呋喃-3(2H)-酮 2-苯甲酰-2-羟基-1-苯并呋喃-3-酮 2-氨基-6-氯-3-硝基吡啶 2-氨基-2-苄基-1-苯并呋喃-3-酮 2-[(Z)-(3,4-二羟基苯基)亚甲基]-6-羟基-7-甲氧基苯并呋喃-3(2H)-酮 2-[(4-羟基-3-甲氧基苯基)亚甲基]-7-甲氧基-1-苯并呋喃-3-酮 2-[(4-硝基苯基)亚甲基]-1-苯并呋喃-3-酮 2-[(4-甲氧基苯基)亚甲基]-5-甲基-1-苯并呋喃-3-酮 2-[(4-溴苯基)亚甲基]-1-苯并呋喃-3-酮 2-[(4-氟苯基)亚甲基]-6-羟基-1-苯并呋喃-3-酮 2-[(4-氟苯基)亚甲基]-6-甲氧基-1-苯并呋喃-3-酮 2-[(4-氟苯基)亚甲基]-5-甲基-1-苯并呋喃-3-酮 2-[(3-甲氧基苯基)亚甲基]-1-苯并呋喃-3-酮 2-[(3-甲基苯基)亚甲基]-1-苯并呋喃-3-酮 2-[(3,4-二甲氧基苯基)亚甲基]-1-苯并呋喃-3-酮 2-(4-甲氧基苯甲酰基)-1-苯并呋喃-3-酮 2-(3,4-二羟基苯甲酰)-2,4,6-三羟基-1-苯并呋喃-3-酮 2-(3,4-二羟基苯亚甲基)-6-羟基-3(2H)-苯并呋喃酮 2-(3,4-二羟基亚苄基)苯并呋喃-3(2H)-酮 1H-萘并[2,1-b]吡喃-2-甲腈,3-氨基-1-(2-氟苯基)- 1,1-二甲基铟烷-5,6-二醇 1,1,2-三甲基肼二盐酸 (Z)-4,6-二羟基橙酮 (Z)-4,6-二羟基橙酮 (7Z)-4-羟基-7-(苯基甲亚基)呋喃并[3,2-e][1,3]苯并二噁唑-8(7H)-酮 (2Z)-4,6-二羟基-2-[(3,4,5-三羟基苯基)亚甲基]-1-苯并呋喃-3-酮 (2E)-2-[(3-硝基苯基)亚甲基]-1-苯并呋喃-3-酮 6-Hydroxy-5-formyl-auron 4'-Methoxy-4.6.7-triacetoxy-auron 4,6,7,3',4'-Pentamethoxy-auron 2-Benzoyl-5-formylcoumaranon 5-Methyl-4,6,3',4'-tetramethoxy-auron 4'-Methoxy-5-formyl-6-hydroxy-auron 7-Formyl-6-hydroxy-auron 6-chloroaurone 4,6,7-Triacetoxy-auron