acerogenin E | 52467-12-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: acerogenin E
• 英文别名: 3,17-dihydroxytricyclo[12.3.1.12,6]nonadeca-1(17),2,4,6(19),14(18),15-hexaen-9-one
• CAS: 52467-12-6
• 化学式: C₁₉H₂₀O₃
• 分子量: 296.366
• InChiKey: HJJZJFOFYZSPGU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  acerogenin E 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以95%的产率得到acerogenin K
  参考文献：
  名称：

  Total synthesis of acerogenins E, G and K, and centrolobol

  摘要：

  The first total synthesis of the diaiylheptanoid acerogenins E and K, isolated from Acer nikoense MAXIM., is described. Formation of the 13-membered m,m-cyclophane skeleton was successfully achieved on the basis of a domino process involving a Miyaura arylborylation intramolecular Suzuki reaction. The cyclization precursor was prepared via a Wittig reaction and Claisen Schmidt condensation, which proceeded in moderate yields. The total synthesis of acerogenin G and centrolobol was also achieved from a common synthetic intermediate. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.01.065
• 作为产物：
  描述：

  4-甲氧基苯甲酸甲酯 在 四氢吡咯 、 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 lithium aluminium tetrahydride 、 草酰氯 、 palladium 10% on activated carbon 、 氢气 、 碘 、 potassium acetate 、 silver trifluoroacetate 、 三溴化硼 、 溶剂黄146 、 硫酸二甲酯 、 联硼酸频那醇酯 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 氯仿 、 二甲基亚砜 为溶剂， 反应 44.25h， 生成 acerogenin E
  参考文献：
  名称：

  Total synthesis of acerogenins E, G and K, and centrolobol

  摘要：

  The first total synthesis of the diaiylheptanoid acerogenins E and K, isolated from Acer nikoense MAXIM., is described. Formation of the 13-membered m,m-cyclophane skeleton was successfully achieved on the basis of a domino process involving a Miyaura arylborylation intramolecular Suzuki reaction. The cyclization precursor was prepared via a Wittig reaction and Claisen Schmidt condensation, which proceeded in moderate yields. The total synthesis of acerogenin G and centrolobol was also achieved from a common synthetic intermediate. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.01.065

文献信息

• Biarylheptanoids and other constituents from wood of Alnus japonica
  作者：Masayasu Nomura、Takashi Tokoroyama、Takashi Kubota

  DOI：10.1016/0031-9422(81)83035-x

  日期：1981.1

  Abstract The wood of Alnus japonica has been shown to contain a number of biarylheptanoids as well as other phenolics, including secoisolariciresinol diferulate. The co-occurrence of cyclized biarylheptanoids with their corresponding acyclic biarylheptanoids has been demonstrated and this fact may have biosynthetic significance. The possible chemotaxonomic importance of biarylheptanoids in members

  摘要 桤木 (Alnus japonica) 的木材已被证明含有许多二芳基庚烷类化合物以及其他酚类物质，包括开环异落叶松树脂二铁。环化联芳基庚烷与其相应的无环联芳基庚烷共存已被证明，这一事实可能具有生物合成意义。讨论了双芳基庚烷在桦木科成员中可能的化学分类学重要性。还描述了几种类固醇和三萜类化合物的分离和鉴定。
• Studies on the Constituents of Aceraceae Plants. XI. Two Types of Cyclic Diarylheptanoid from Acer nikoense.
  作者：Seiji NAGUMO、Norihiro KAJI、Takao INOUE、Masahiro NAGAI

  DOI：10.1248/cpb.41.1255

  日期：——

  Two diarylheptanoid glycosides, acerosides V (1) and XI (2), were isolated from the stem bark of Acer nikoense MAXIM. (Aceraceae). On hydrolysis, 1 and 2 yielded new diarylheptanoids, acerogenin D (6) and acerogenin E (7), respectively. Acerogenin D (6) was chemically correlated with acerogenin C (5), and acerogenin E, with alnusone (8). On the basis of the chemical and spectroscopic evidence, the chemical structures of 1 and 2 were established as the 2-O-β-D-glucopyranoside of acerogenin D and 3-O-β-D-glucopyranoside of acerogenin E, respectively. Aceroside XI is the first example of the biphenyl type of diarylheptanoid isolated from this plant. A. nikoense thus contains three types of diarylheptanoid, linear, cyclic biphenyl and cyclic diphenyl ether types.

  从Acer nikoense MAXIM（槭树科）的茎皮中分离出两种二芳基庚烷苷，即槭苷V（1）和槭苷XI（2）。水解后，1和2分别产生了新的二芳基庚烷苷，即槭苷D（6）和槭苷E（7）。槭苷D（6）与槭苷C（5）在化学上相关，而槭苷E与桤木酮（8）相关。根据化学和光谱学证据，1和2的化学结构分别确定为槭苷D的2-O-β-D-吡喃葡萄糖苷和槭苷E的3-O-β-D-吡喃葡萄糖苷。槭苷XI是从这种植物中分离出的第一个二苯基型二芳基庚烷苷。因此，A. nikoense含有三种类型的二芳基庚烷苷，即线型、环状二苯基和环状二苯醚。
• Studies on the Constituents of Aceraceae Plants. XIII. Diarylheptanoids and Other Phenolics from Acer nikoense.
  作者：Seiji NAGUMO、Sumiko ISHIZAWA、Masahiro NAGAI、Takao INOUE

  DOI：10.1248/cpb.44.1086

  日期：——

  From a mixture of the bark and twigs of Acer nikoense MAXIM. (Aceraceae), nine compounds (1-9) were newly isolated. Compound 1 was identical with acerogenin E, and compounds 8 and 9 were β-orcinol derivatives. Acerogenin K (2), a new diarylheptanoid of the cyclic diphenyl type, yielded acerogenin E on oxidation. Acerogenins F (3) through L (7) are new diarylheptanoids of the cyclic biphenyl ether type, whose skeletons and substituents of the diphenyl ether moieties are the same as those of acerogenin A. Their structures were elucidated on the basis of chemical and spectroscopic evidence.

  从槭树（Acer nikoense MAXIM.）的树皮和树枝混合物中，新分离出9种化合物（1-9）。化合物1与槭树素E相同，化合物8和9是β-orcinol衍生物。槭树素K（2）是一种新的环状二苯基型二芳基庚烷，在氧化后生成槭树素E。槭树素F（3）至L（7）是新的环状二苯醚型二芳基庚烷，其骨架和二苯醚部分的取代基与槭树素A相同。它们的结构是根据化学和光谱证据阐明的。
• [EN] ANTIMICROBIALS AS FEED PRESERVATIVES<br/>[FR] AGENTS ANTIMICROBIENS UTILISÉS EN TANT QUE CONSERVATEURS ALIMENTAIRES
  申请人：IRP HEALTH PTY LTD

  公开号：WO2021072473A1

  公开（公告）日：2021-04-22

  The present disclosure relates to an animal feed preservative or animal feed comprising one or more antimicrobial agents, wherein the one or more antimicrobial agents are selected from: one or more berberine alkaloids; one or more ursane-like triterpenoids; one or more phenylpropanoids; one or more monoterpenoids; or mixtures thereof. In particular, the present disclosure relates to a safe animal feed preservative or animal feed comprising the aforementioned antimicrobial agents.
• Total synthesis of acerogenins E, G and K, and centrolobol
  作者：Tetsuhiro Ogura、Toyonobu Usuki

  DOI：10.1016/j.tet.2013.01.065

  日期：2013.4

  The first total synthesis of the diaiylheptanoid acerogenins E and K, isolated from Acer nikoense MAXIM., is described. Formation of the 13-membered m,m-cyclophane skeleton was successfully achieved on the basis of a domino process involving a Miyaura arylborylation intramolecular Suzuki reaction. The cyclization precursor was prepared via a Wittig reaction and Claisen Schmidt condensation, which proceeded in moderate yields. The total synthesis of acerogenin G and centrolobol was also achieved from a common synthetic intermediate. (C) 2013 Elsevier Ltd. All rights reserved.