methyl (4aS,6aR,6bS,8aR,10S,12aS,14bS)-10-acetoxy-2,2,6a,6b,9,9,12a-heptamethyl -1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14b-hexadecahydropicene-4a(2H)-carboxylate | 108631-02-3

• 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: methyl (4aS,6aR,6bS,8aR,10S,12aS,14bS)-10-acetoxy-2,2,6a,6b,9,9,12a-heptamethyl -1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14b-hexadecahydropicene-4a(2H)-carboxylate
• 英文别名: methyl 3β-acetoxyolean-9(11),12-dien-28-oate；3β-acetoxy-oleanadien-(9(11).12)-oic acid-(28)-methyl ester；3β-Acetoxy-oleanadien-(9(11).12)-saeure-(28)-methylester；methyl (4aS,6aR,6bS,8aR,10S,12aS,14bS)-10-acetyloxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,7,8,8a,10,11,12,14b-dodecahydropicene-4a-carboxylate
• CAS: 108631-02-3
• 化学式: C₃₃H₅₀O₄
• 分子量: 510.758
• InChiKey: SMYZGGMZHRPMLA-FEFFLPIYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  37
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (4aS,6aR,6bS,8aR,10S,12aS,14bS)-10-acetoxy-2,2,6a,6b,9,9,12a-heptamethyl -1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14b-hexadecahydropicene-4a(2H)-carboxylate 在 ruthenium trichloride 、 sodium periodate 、 碘 作用下， 以 乙醇 、 正己烷 、 水 、 丙酮 为溶剂， 反应 8.5h， 生成 ((4aS,8aS)-8-Hydroxymethyl-2,2,7-trimethyl-1,3,4,5,6,8a-hexahydro-2H-naphthalen-4a-yl)-methanol
  参考文献：
  名称：

  Degradation of triterpenic compounds from olive-pressing residues. Synthesis of trans-decalin type chiral synthons

  摘要：

  Three seco-Gring triterpenic compounds were obtained from oleanolic or maslinic acids from olive-mill solid wastes by photochemical and chemical reactions. From these oleantriene compounds, different remarkable sesquiterpene and nor-sesquiterpene fragments such as 3beta-hydroxydrimenol (13) and epoxydecalone (16) were achieved through oxidative cleavages of the double bonds in the opened Gring. (C) 2003 Published by Elsevier Ltd.

  DOI：

  10.1016/s0040-4039(03)01634-4
• 作为产物：
  描述：

  3β-hydroxyoleana-9(11),12-dien-28-oic acid 在 吡啶 作用下， 以 甲醇 、 乙醚 为溶剂， 生成 methyl (4aS,6aR,6bS,8aR,10S,12aS,14bS)-10-acetoxy-2,2,6a,6b,9,9,12a-heptamethyl -1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14b-hexadecahydropicene-4a(2H)-carboxylate
  参考文献：
  名称：

  Structure and Spasmolytic Activity of Eucalyptanoic Acid from Eucalyptus camaldulensis var. obtusa and Synthesis of Its Active Derivative from Oleanolic Acid

  摘要：

  A new triterpenoid acid named eucalyptanoic acid (1) has been isolated from the fresh uncrushed leaves of Eucalyptus camaldulensis var. obtusa along with two known constituents, beta-sitosterol (2) and betulinic acid (3). The structure of 1 has been established as 3beta-hydroxyolean-9(11),12-dien-28-oic acid through spectral studies including 1D and 2D NMR. 1 and its acetyl (1a) and acetylmethyl (1b) derivatives were tested for spasmolytic activity. 1b was found to be the most active spasmolytic, mediated through blockade of calcium influx at 1 mg/mL. In the present study lb was also prepared starting from oleanolic acid (4). Acetylation. of 4 gave 4a, which on methylation afforded 4b. Reaction of 4b with N-bromosuccinimide (NBS) furnished 1b. Hence 4 may be regarded as the biogenetic precursor of 1. Compounds 4 and 4a were found inactive at 1 mg/mL,while 4b was moderately active in showing spasmolytic activity.

  DOI：

  10.1021/np020127x

文献信息

• Partial synthesis of C-ring derivatives from oleanolic and maslinic acids. Formation of several triene systems by chemical and photochemical isomerization processes
  作者：Andrés Garcı́a-Granados、Pilar E López、Enrique Melguizo、Andrés Parra、Yolanda Simeó

  DOI：10.1016/j.tet.2003.12.023

  日期：2004.2

  Some triterpenic compounds modified in C-ring were semi-synthesised from oleanolic acid contained in the solid waste of olive-oil pressing. The corresponding esters of oleanolic and maslinic acids rendered products with a diene system, which led to oleantrienes resembling previtamin D2 by an electrocyclic reaction. Chemical and photochemical isomerization of these compounds yielded two different trienes

  从橄榄油压榨固体废物中所含的齐墩果酸半合成了一些在C环上改性的三萜类化合物。齐墩果酸和山lin酸的相应酯使产物具有二烯体系，其通过电环反应产生类似于维生素原D 2的油烯酮。这些化合物的化学和光化学异构化反应产生了两种不同的三烯，其结构与速甾醇和维生素D 2相似。
• 杂萜类天然产物(+)-Arisugacins F/G的全合 成方法
  申请人：中国海洋大学

  公开号：CN110845512B

  公开（公告）日：2020-09-18

  本发明公开了杂萜类天然产物(+)‑ArisugacinsF/G的全合成方法，属于有机合成领域。以齐墩果酸为手性源起始原料，经过活性基团保护、自由基消除、开环反应、顺反异构化和氧化水解得到手性中间体醛；接着与吡喃酮经过[3+3]环加成反应，氢化还原生成(+)‑Arisugacins F；随后发生氧化反应得到(+)‑Arisugacins G。本发明中，手性源起始原料齐墩果酸商业易得，反应过程中各单元反应条件温和可控，关键反应立体选择性强，在杂萜类天然产物全合成和药物发现中具有潜在的应用价值。
• Total syntheses of (+)-arisugacins F, G
  作者：Ping Chen、Hao Wu、Yu Li、Yu Tang

  DOI：10.1016/j.tetlet.2020.152172

  日期：2020.8

  (+)-Arisugacin F and G are synthesized from commercially available oleanolic acid in 9 and 10 steps, respectively. This strategy features a AgOTf/Pd(PPh3)4-mediated cis/trans olefin isomerization and a highly convergent formal oxa-[3 + 3] cycloaddition between key α, β-unsaturated aldehyde and pyrone, which lays the foundation for efficient and concise synthesis of other natural products with similar

  （+）-Arisugacin F和G分别由市售的齐墩果酸分9步和10步合成。该策略具有AgOTf / Pd（PPh 3）4介导的顺式/反式烯烃异构化和关键α，β-不饱和醛与吡喃酮之间高度收敛的形式oxa- [3 + 3]环加成的特点，这为高效和精简合成具有类似萜类骨架的其他天然产物。
• Midazolam attenuates ketamine-induced abnormal perception and thought process but not mood changes
  作者：Manzo Suzuki、Kentaro Tsueda、Peter S. Lansing、Merritt M. Tolan、Thomas M Fuhrman、Rachel A. Sheppard、Harrell E. Hurst、Steven B. Lippmann

  DOI：10.1007/bf03019666

  日期：2000.9

  Purpose: To determine the effects of midazolam, 30 ng.mL(-1), on altered perception, mood, and cognition induced by ketamine.Methods: After ketamine was administered to achieve target concentrations of 50, 100, or 150 ng.mL(-1) in 11 volunteers, perception, mood, and thought process were assessed by a visual analog scale. Mini-Mental State examination (MMSE) assessed cognition. Boluses of midazolam, 30, 14.5, and 12 mu g.kg(-1), were injected every 30 min to maintain the plasma concentration at 30 ng.mL(-1), which was reached 30 min after each injection.Results: Ketamine produced changes in perception about the body (P < 0.01, 0.001, and 0.0001 at 30, 60, and 90 min), surroundings (P < 0.01 and 0.0001 at 60 and 90 min), time (P < 0.002 and 0.0001 at 60 and 90 min), reality (P < 0.001 and 0.0001 at 60 and 90 min), sounds (P < 0.002 at 90 min), and meaning(P < 0.05 at 30 min), Subjects felt less energetic and clearheaded (P < 0.02 and 0.05) during ketamine, midazolam, and their coadministration. Ketamine impaired thought process (P < 0.003 and 0.0001 at 60 and 90 min). Ketamine and midazolam decreased mean total MMSE and recall scores (P < 0.001 for both). Go-administration reduced the number of subjects with perceptual (body, P < 0.01 and 0.001 at 30 and 60 min) and thought process abnormalities. Within the range of observation, co-administration did not affect the changes in mood or recall.Conclusion: Midazolam attenuates ketamine-induced changes in perception and thought process.
• Oxidation of several triterpenic diene and triene systems. Oxidative cleavage to obtain chiral intermediates for drimane and phenanthrene semi-synthesis
  作者：Andrés Garcı́a-Granados、Pilar E López、Enrique Melguizo、Andrés Parra、Yolanda Simeó

  DOI：10.1016/j.tet.2004.03.008

  日期：2004.4

  An exhaustive oxidation study has been made with ozone, MCPBA and/or NaIO4/RuCl3 of several triterpenic diene and triene compounds from oleanolic and maslinic acids obtained from olive-oil pressing. Through several oxidative cleavages of the opened C-ring of these oleantrienes, different significant decalin-type chiral synthons were achieved. These sesquiterpene and nor-sesquiterpene products are of great interest because by means of several simple reactions they could lead to drimane, phenanthrene and tricyclic triterpene compounds. (C) 2004 Elsevier Ltd. All rights reserved.