linifolin A | 5988-99-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: linifolin A
• 英文别名: [(3aS,5R,5aR,8aR,9R,9aR)-5,8a-dimethyl-1-methylidene-2,8-dioxo-3a,4,5,5a,9,9a-hexahydroazuleno[6,5-b]furan-9-yl] acetate
• CAS: 5988-99-8
• 化学式: C₁₇H₂₀O₅
• 分子量: 304.343
• InChiKey: DCNRYQODUSSOKC-JKSXDGAISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 linifolin A 以 甲醇 、 乙醚 为溶剂， 以100%的产率得到[(3'aS,5R,5'R,5'aR,8'aR,9'R,9'aR)-5',8'a-dimethyl-2',8'-dioxospiro[3,4-dihydropyrazole-5,1'-3a,4,5,5a,9,9a-hexahydroazuleno[6,5-b]furan]-9'-yl] acetate
  参考文献：
  名称：

  The stereochemistry of the 1,3-dipolar cycloadditions of diazomethane to pseudoguaianolides

  摘要：

  The 1,3-dipolar cycloaddition of diazomethane to the sesquiterpene lactones, parthenin, coronopilin, and psilostachyin, gave their respective spiropyrazolines with complete chemoselectivity, while the diastere-oselectivity in favour of the (11S)-stereoisomer was 86-98%. Similarly, mexicanin I acetate, helenalin, and helenalin acetate provided the (11R)-diastereoisomer. When helenalin and its acetate were treated with a large excess of diazomethane, they afforded their respective dipyrazolines with 98% diastere-oselectivity in favour of the (2R,3S,11R)-diastereoisomer. All compounds were characterized by their physical and spectroscopic properties and their absolute configuration was established by X-ray diffraction analysis calculating the Flack and Hooft parameters. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2017.01.009
• 作为产物：
  描述：

  (3aα,4β,4aβ,5β,7aα,8α,9aβ)-3a,4,4a,5,7a,8,9,9a-Octahydro-4-hydroxy-4a,8-dimethyl-5-(phenylmethoxy)azuleno<6,5-b>-furan-2(3H)-one 在 4-二甲氨基吡啶 、 manganese(IV) oxide 、 对甲苯磺酸 、 1,5-Diazabicyclo[5.4.0]undec-5-ene 作用下， 以 吡啶 、 二氯甲烷 、 水 、 溶剂黄146 、 苯 为溶剂， 反应 10.5h， 生成 linifolin A
  参考文献：
  名称：

  Helenanolides: stereocontrolled total synthesis of dl-bigelovin, dl-mexicanin I, and dl-linifolin A

  摘要：

  DOI：

  10.1021/jo00151a016

文献信息

• Structure−Cytotoxicity Relationships of Some Helenanolide-Type Sesquiterpene Lactones
  作者：Aäron C. Beekman、Herman J. Woerdenbag、Wim van Uden、Niesko Pras、Antonius W. T. Konings、Håkan V. Wikström、Thomas J. Schmidt

  DOI：10.1021/np960517h

  日期：1997.3.1

  This study deals with the cytotoxicity of helenanolide-type (10 alpha-methylpseudoguaianolide) sesquiterpene lactones. We determined the influence of substitution patterns on the toxicity of 21 helenanolides to a cloned Ehrlich ascites tumor cell line, EN2. Within a series of helenalin esters, the acetate (2) and isobutyrate (3) were more toxic than helenalin itself (1). Esters with larger acyl groups

  这项研究涉及的Helenanolide型（10α-甲基伪guaianolide）倍半萜内酯的细胞毒性。我们确定了替代模式对21种helenanolides对克隆的Ehrlich腹水肿瘤细胞系EN2毒性的影响。在一系列海蓝灵酯中，乙酸酯（2）和异丁酸酯（3）比海蓝灵本身（1）更具毒性。与母体醇（1）相比，具有较大酰基（酯4和异戊酸酯5）的酯显示出降低的毒性。Helalalin的6,8-非对映异构体，Mexcanin I（6）和其乙酸盐（7）和异戊酸酯（8）之间观察到相似的关系。与此相反，一系列11种α，13-二氢海那那酯（9-12）的细胞毒性显示出与酯侧链的大小和亲脂性直接相关，二氢Helenalin（9）是该组中毒性最小的化合物。研究了几种带有2个α-羟基-4-氧代和2个α，4个α-二羟基或-O-酰基取代的环戊烷环的2,3-二氢海那灵衍生物（13-21），分别是阿尼福林和香米油苷迄今为止，
• The stereochemistry of the 1,3-dipolar cycloadditions of diazomethane to pseudoguaianolides
  作者：Adriana Ortiz-León、J. Martín Torres-Valencia、J. Jesús Manríquez-Torres、José G. Alvarado-Rodríguez、Carlos M. Cerda-García-Rojas、Pedro Joseph-Nathan

  DOI：10.1016/j.tetasy.2017.01.009

  日期：2017.2

  The 1,3-dipolar cycloaddition of diazomethane to the sesquiterpene lactones, parthenin, coronopilin, and psilostachyin, gave their respective spiropyrazolines with complete chemoselectivity, while the diastere-oselectivity in favour of the (11S)-stereoisomer was 86-98%. Similarly, mexicanin I acetate, helenalin, and helenalin acetate provided the (11R)-diastereoisomer. When helenalin and its acetate were treated with a large excess of diazomethane, they afforded their respective dipyrazolines with 98% diastere-oselectivity in favour of the (2R,3S,11R)-diastereoisomer. All compounds were characterized by their physical and spectroscopic properties and their absolute configuration was established by X-ray diffraction analysis calculating the Flack and Hooft parameters. (C) 2017 Elsevier Ltd. All rights reserved.
• Helenanolides: stereocontrolled total synthesis of dl-bigelovin, dl-mexicanin I, and dl-linifolin A
  作者：Paul A. Grieco、Yasufumi Ohfune、George F. Majetich

  DOI：10.1021/jo00151a016

  日期：1983.2