28-oxo-allobetulone | 24099-81-8

• 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: 28-oxo-allobetulone
• 英文别名: (1R,4R,5R,8R,13R,14R,17R,18R,19R)-4,5,9,9,13,20,20-heptamethyl-24-oxahexacyclo[17.3.2.01,18.04,17.05,14.08,13]tetracosane-10,23-dione
• CAS: 24099-81-8
• 化学式: C₃₀H₄₆O₃
• 分子量: 454.693
• InChiKey: NJVHLJAPSJFFSB-VTUUROQVSA-N

物化性质

• 熔点：
  333-334 °C
• 沸点：
  554.4±23.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  33
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  28-oxo-allobetulone 在 lithium aluminium tetrahydride 、 水 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 3.0h， 以60%的产率得到oleanan-3β,19β,28-triol
  参考文献：
  名称：

  Synthesis of olean-18(19)-ene derivatives from betulin

  摘要：

  The rare olean-18(19)-ene triterpenoids moradiol and moronic acid were synthesized from betulin, and their antiviral properties were investigated.

  DOI：

  10.1134/s1068162009020125
• 作为产物：
  描述：

  路路通酸 在 甲酸 作用下， 生成 28-oxo-allobetulone
  参考文献：
  名称：

  Effective synthesis of 2,3-seco-2,3-dicarboxyplatanic acid

  摘要：

  提出了一种有效的方法，通过臭氧解离反应制备三萜类2,3-分离-2,3-二酸，该反应利用了2-外甲撑取代的贝图隆酸衍生物和28-氧代全贝图隆的衍生物。

  DOI：

  10.1007/s10600-010-9626-1

文献信息

• Synthesis and cytotoxicity of allobetulin derivatives
  作者：O. B. Kazakova、I. E. Smirnova、E. F. Khusnutdinova、O. S. Zhukova、L. V. Fetisova、G. N. Apryshko、N. I. Medvedeva、E. Yu. Yamansarov、I. P. Baikova、Thanh Tra Nguyen、H. Do Thi Thu

  DOI：10.1134/s1068162014050082

  日期：2014.9

  The synthesis and screening of antitumor activity in vitro (cytotoxicity) of various oxygen, nitrogen, sulfur and platinum-containing derivatives of allobetulin, including different arrangements of the double bonds in the A and B rings, penta- and hexacyclic ring A, 21-acetyl-20,28-epoxy-18α,19βH-ursane-isomeric cycle E, was carry out. (3R,5R)-19β,28-Epoxy-4,5-seco-18α-olean-3(5)-ozonide and 2,3-i

  合成和筛选多种别氧白蛋白的含氧，氮，硫和铂的体外抗肿瘤活性（细胞毒性），包括A和B环，五环和六环A，21-进行了乙酰基-20,28-环氧-18α，19βH-ur烷异构体循环E。（3R，5R）-19β，28-环氧-4,5-seco-18α-olean-3（5）-臭氧化物和2,3-吲哚-21β-乙酰基-20β，28-环氧-18α，H-19β -ursane适当地显示了对黑色素瘤MeWo和白血病SR细胞的显着细胞毒活性。第一化合物的（3S，5S）-非对映异构体没有显示细胞毒性。
• Bismuth triflate-catalyzed Wagner-Meerwein rearrangement in terpenes. Application to the synthesis of the 18α-oleanane core and A-neo-18α-oleanene compounds from lupanes
  作者：Jorge A. R. Salvador、Rui M. A. Pinto、Rita C. Santos、Christophe Le Roux、Ana Matos Beja、José A. Paixão

  DOI：10.1039/b814448f

  日期：——

  catalysts for the Wagner-Meerwein rearrangement of lupane derivatives with expansion of ring E and formation of an additional O-containing ring is reported. This process has also been extended to other terpenes, such as the sesquiterpene (−)-caryophyllene oxide. When the reaction was performed with oleanonic acid, 28,13β-lactonization occurred, without Wagner-Meerwein rearrangement. Under more vigorous reaction

  据报道，使用铋（III）盐作为戊烷衍生物的瓦格纳-梅尔文重排，并伴随环E的膨胀和形成另外的含O的环的催化剂的使用。此过程也已扩展到其他萜烯，例如倍半萜烯（-）-石竹烯氧化物。当用齐墩果酸，发生28,13β-内酯化，没有Wagner-Meerwein重排。在更剧烈的反应条件下，3β-羟基的脱水和随后的额外的Wagner-Meerwein重排导致以极高的收率选择性合成A- neo -18α-亚麻烯化合物。
• Stereoselectivity of A-ring contraction for 3-oxotriterpenoids
  作者：Alexey D. Kacharov、Sergiy V. Yemets、Victor N. Nemykin、Liliya M. Kacharova、Andrey A. Fokin、Pavel A. Krasutsky

  DOI：10.1039/c3ra42929f

  日期：——

  The A-ring oxidation/contraction of 3-oxotriterpenoids was developed as a two-step and “one pot” process. A benzylic acid type rearrangement of triterpenoid diosphenols gives (S)- as major and (R)-α-hydroxycarboxylic acids as minor reaction products. The absolute configurations were determined from the X-ray crystal structure analysis. The mechanism of ring contraction was modelled computationally at the DFT and MP2 levels of theory. The tautomeric triterpenoid A-seco δ-oxocarboxylic acids and A-ring hydroxy lactones formed after deep oxidation/acidification of 3-oxotriterpenoids.

  3-氧代三萜类化合物的A环氧化/缩合反应被开发为两步和“一步法”过程。三萜二酚的苄酸型重排主要生成(S)-型α-羟基羧酸，次要生成(R)-型α-羟基羧酸。绝对构型通过X射线晶体结构分析确定。环缩合机制在DFT和MP2理论水平上进行了计算模拟。3-氧代三萜类化合物经过深度氧化/酸化后形成的A环开裂δ-氧代羧酸和A环羟基内酯。
• Cyclopropanation of betulonic acid and its methyl ester with dichlorocarbene generated under phase transfer catalysis conditions
  作者：N. G. Komissarova、N. G. Belenkova、O. V. Shitikova、L. V. Spirikhin、M. S. Yunusov

  DOI：10.1007/s11172-006-0173-7

  日期：2005.11

  The addition of dichlorocarbene generated under phase transfer catalysis conditions to the double bond of betulonic acid occurs stereoselectively and is accompanied by transformation of the carboxy group leading to the dichloromethyl ester and chloride of 3-oxo-20,29-(dichloromethano)lupan-28-oic acid. Together these products, the chloride of the starting betulonic acid is formed depending on the reaction

  在相转移催化条件下生成的二氯卡宾与桦木酸的双键发生立体选择性的加成，并伴随着羧基的转化，生成 3-oxo-20,29-(dichloromethano)lupan-28 的二氯甲酯和氯化物-油酸。根据反应条件，这些产物一起形成起始桦木酸的氯化物。二氯卡宾与桦木酸甲酯反应以定量产率生成相应的环丙烷加合物。
• Synthesis and evaluation of 2,3-indolotriterpenoids as new α-glucosidase inhibitors
  作者：Elmira F. Khusnutdinova、Irina E. Smirnova、Oxana B. Kazakova、Anastasiya V. Petrova、Nguyen Thi Thu Ha、Do Quoc Viet

  DOI：10.1007/s00044-017-1972-0

  日期：2017.11

  AbstractA series of ring-A fused heterocycles of lupane, oleanane, ursane and dammarane triterpenoids were synthesized and evaluated for their inhibitory activity against α-glucosidase. An influence of the different types of triterpenoids with indole and pyrazine cycles on the activity was revealed. Among them, 2,3-indolo-lup-20(29)-en-28-oic acid with an IC50 of 1.8 µM was the most active compound

  摘要合成了一系列环戊烷，齐墩果烷，乌尔烷和达玛烷三萜类化合物的A环稠合杂环，并评估了其对α-葡萄糖苷酶的抑制活性。揭示了吲哚和吡嗪循环不同类型的三萜类化合物对活性的影响。其中，IC 50为1.8 µM的2,3-吲哚-lup-20（29）-en-28-油酸是活性最高的化合物，其活性是市售阿卡波糖的221倍。在大多数情况下，用吡嗪片段取代吲哚会降低活性（除了达玛烷型吡嗪衍生物）。 图形概要