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(3aS,5R,7aS)-5-[(1E,6S)-6-(4-methoxybenzyloxy)-1-heptenyl]hexahydrofuro[3,2-b]pyran-2-one | 1204616-82-9

中文名称
——
中文别名
——
英文名称
(3aS,5R,7aS)-5-[(1E,6S)-6-(4-methoxybenzyloxy)-1-heptenyl]hexahydrofuro[3,2-b]pyran-2-one
英文别名
(3aS,5R,7aS)-5-[(E,6S)-6-[(4-methoxyphenyl)methoxy]hept-1-enyl]-3,3a,5,6,7,7a-hexahydrofuro[3,2-b]pyran-2-one
(3aS,5R,7aS)-5-[(1E,6S)-6-(4-methoxybenzyloxy)-1-heptenyl]hexahydrofuro[3,2-b]pyran-2-one化学式
CAS
1204616-82-9
化学式
C22H30O5
mdl
——
分子量
374.477
InChiKey
NKPCXCBVJFAKJW-GEJWFTEBSA-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):
    3.6
  • 重原子数:
    27
  • 可旋转键数:
    9
  • 环数:
    3.0
  • sp3杂化的碳原子比例:
    0.59
  • 拓扑面积:
    54
  • 氢给体数:
    0
  • 氢受体数:
    5

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

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文献信息

  • Synthesis of aspergillide A from a synthetic intermediate of aspergillide B
    作者:Tomohiro Nagasawa、Shigefumi Kuwahara
    DOI:10.1016/j.tetlet.2009.12.032
    日期:2010.2
    The first synthesis of aspergillide A, a cytotoxin produced by a marine-derived fungus, has been achieved from a synthetic intermediate of aspergillide B by using a proline-mediated epimerization of a 2,6-trans-substituted tetrahydropyran-2-acetaldehyde intermediate into the corresponding cis-isomer via a retro-oxy-Michael/oxy-Michael sequence as the key transformation.
    曲霉内酯A的第一次合成是由海洋真菌产生的细胞毒素,它是由曲霉内酯B的合成中间体通过脯氨酸介导的2,6-反式取代的四氢吡喃-2-乙醛中间体差向异构化成相应的顺式异构体通过反-氧-迈克尔/氧-迈克尔序列作为关键转化。
  • Enantioselective Synthesis of Aspergillide B
    作者:Tomohiro NAGASAWA、Shigefumi KUWAHARA
    DOI:10.1271/bbb.90221
    日期:2009.8.23
    The enantioselective synthesis of aspergillide B, a 14-membered macrocyclic cytotoxin, was achieved in a 49% yield via 7 steps from a synthetic intermediate of aspergillide C. The spectroscopic data and specific rotation value for the synthetic material matched those of natural aspergillide B.
    由曲霉内酯C的合成中间体经过7个步骤,以49%的产率实现了对映体选择性合成14元大环细胞毒素的曲霉内酯B.合成材料的光谱数据和比旋光度与天然曲霉内酯B的光谱数据和比旋光度匹配。
  • Synthesis of aspergillide A via proline-catalyzed trans-to-cis isomerization of a substituted tetrahydropyran
    作者:Tomohiro Nagasawa、Tomoo Nukada、Shigefumi Kuwahara
    DOI:10.1016/j.tet.2011.02.061
    日期:2011.4
    The transformation of a common synthetic intermediate of aspergillides B and C into aspergillide A, a cytotoxin produced by a marine-derived fungus, has been accomplished in an eleven-step sequence involving an efficient proline-catalyzed isomerization of a 2,6-trans-substituted tetrahydropyran-2-acetaldehyde intermediate into the corresponding cis isomer and the Yamaguchi macrolactonization as the key steps. (C) 2011 Elsevier Ltd. All rights reserved.
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同类化合物

马桑宁内酯 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 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 5-hydroxymethyl-3-methyl-2H-furo[2,3-c]pyran-2-one 5-fluoromethyl-2H-furo[2,3-c]pyran-2-one 5-chloromethyl-2H-furo[2,3-c]pyran-2-one 10,11-Anhydro-5-deoxy-1,2-O-isopropylidene-9-O-(methoxymethyl)-β-L-xylo-L-ido-7-undeculofuranose-(1,4)-pyranose-(7,3) 3,7-dimethyl-2H-furo[2,3-c]pyran-2-one 4R-(3αβ,3aβ,4β,5α,6β,7aβ)hexahydro-2,2-dimethyl-4,5-bis(phenylmethoxy)-6-[(phenylmethoxy)methyl]4H-furo[2,3-b]pyran-3-ol 10,10-dimethyl-5-(methylsulfanyl)-10,11-dihydro-8H-pyrano[4',3':4,5]furo[3,2-e]tetrazolo[1,5-c]pyrimidine (R)-3-((2R,3R,5aR,7R,9aS)-3-hydroxyhexahydro-2H-2,5a-methanopyrano[3,2-e][1,4]dioxepin-7-yl)-2-methylpropanenitrile 13-methyl-8,10,12-trioxapentacyclo[5.5.2.02,6.O3,11.05,9]-13-tetradecene 2,3,4,4a,7,8-Hexahydro-6H-2-(acetoxymethyl)-3,4-diacetoxy-1,9-dioxacyclohexainden-5-one 2,3,4,4a,7,8-Hexahydro-6H-2-methoxy-1,9-dioxacyclohexainden-5-one (-)-3a-methyl-3a,4-dihydro-1H,3H-furo[3,4-c]pyran-6,6,7-tricarboxylic acid 6,6-diethyl ester 7-methyl ester (+)-8-epi-altholactone 4-(perfluorophenyl)-3-phenylhexahydro-1H-furo[3,4-c]pyran [(2R,11S,12R,14R,15R,17R,19S)-19-tert-butyldiphenylsiloxymethyl-15-methyl-13,18-dioxadispiro(2H-3,6-dihydropyran-6,5'-oxolane-2',3''-bicyclo[4.3.0]nonane)-2-yl]phenylmethoxymethane (3aS,5S,9bS)-5-methyl-3,3a-dihydro-5H-furo[3,2-c]isochromene-2,6,9-(9bH)-trione (3aR,5R,7aR)-5-(2-hydroxypropan-2-yl)-7a-methylhexahydro-2H-furo[3,2-b]pyran-2-one 2,2,3b-trimethyl-7-vinyl-3a,5,7a,8a-tetrahydro-3bH-1,3,4,8-tetracyclopenta[a]indene ethyl 4-oxo-3-phenyl-3,3a,4,6-tetrahydro-1H-furo[3,4-c]pyran-3a-carboxylate methyl (2R,2aR,4aS,7aS,7bS)-2-methoxy-6-methyl-4-oxo-5-pentyl-2a,4,4a,7b-tetrahydro-2H-1,3,7-trioxacyclopenta[cd]indene-7a-carboxylate 4-nonyl-3-phenylhexahydro-1H-furo[3,4-c]pyran 3'-(4-methoxyphenyl)-7a'-methyl-4'H,6'H-spiro[cyclohexane-1,5'-furo[2,3-b]pyran]-2'(7a'H)-one 3',7a'-dimethyl-4'H,6'H-spiro[cyclohexane-1,5'-furo[2,3-b]pyran]-2'(7a'H)-one 2-(methylsulfanyl)-5,6-dihydro-4H-furo[2,3-b]pyran 1,1-(3-dimethylamino-3-phenylpentamethylen)-3,4-dihydro-1H-2,9-dioxafluoren 7-cyclopropyl-4,5,7,7a-tetrahydro-furo[2,3-c]pyran-2-one 7-cyclopropyl-3-phenyl-4,5,7,7a-tetrahydro-furo[2,3-c]pyran-2-one 7-cyclopropyl-3-phenyl-4,5,7,7a-tetrahydro-furo[2,3-c]pyran-2-one (4'R)-6-O-(4-cyanophenyl)-1,2,3,4-tetradeoxy-4'-(2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,9-heptadecafluorononyl)-2',3',4',5'-tetrahydro-α-D-erythro-hexopyranoso[1,2-b]furan 2,2,3,6-tetramethyl-2,3-dihydro-4H-furo[2,3-b]pyran-4-one (1aR,4aS,5R)-7-carboethoxy-5-methylethyl-tetrahydrofurano[2,3-b]3,4-dihydro-2H-pyran (3aS,4S,7aR)-ethyl 4-methyl-3,3a,4,7a-tetrahydro-2H-furo[2,3-b]pyran-6-carboxylate