1,2,6,6,10,16,17-heptamethyl-20-(acetoxymethyl)pentacyclo[12.8.0.0^2.11.0^5.10.0^15.20]docos-17-en-7-yl acetate | 38602-40-3

• 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: 1,2,6,6,10,16,17-heptamethyl-20-(acetoxymethyl)pentacyclo[12.8.0.0^2.11.0^5.10.0^15.20]docos-17-en-7-yl acetate
• 英文别名: 3β,28-diacetoxy-18α,19βH-urs-20-ene；3β,28-diacetoxy-18αH,19βH-ursan-20-en；Diacetylheterobetulin；heterobetulin diacetate；Heterobetulin-diacetat；[(1S,4aR,6aR,6aR,6bR,8aR,10S,12aR,14aR,14bR)-10-acetyloxy-1,2,6a,6b,9,9,12a-heptamethyl-4,5,6,6a,7,8,8a,10,11,12,13,14,14a,14b-tetradecahydro-1H-picen-4a-yl]methyl acetate
• CAS: 38602-40-3
• 化学式: C₃₄H₅₄O₄
• 分子量: 526.8
• InChiKey: LUHAUIAIHYEWGW-ZXVILCOISA-N

物化性质

• 熔点：
  248-249 °C
• 沸点：
  547.8±23.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  38
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.88
• 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：

  1,2,6,6,10,16,17-heptamethyl-20-(acetoxymethyl)pentacyclo[12.8.0.0^2.11.0^5.10.0^15.20]docos-17-en-7-yl acetate 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 heterobetulin
  参考文献：
  名称：

  An efficient synthesis of moronic and heterobetulonic acids from allobetulin

  摘要：

  The reaction of acetoxyallobetulin with HClO4 in refluxing Ac2O led to a mixture of diacetoxyheterobetulin (3 beta,28-diacetoxy-18 alpha,19 beta H-urs-20-ene), diacetoxymoradiol (3 beta,28-diacetoxy-olean-18(19)-ene), 3 beta-acetoxy-21 beta-acetyl-20 beta,28-epoxy-18 alpha,19 beta H-ursane, and diacetoxy-delta-erythrodiol (3 beta,28-diacetoxy-olean-13(beta)-ene), which were isolated by column chromatography in yields of 18%, 37%, 39%, and 2%, respectively. Deacetylation of diacetoxyheterobetulin and diacetoxymoradiol followed by Jones oxidation of the corresponding triterpene 3 beta,28-diols led to heterobetulonic and moronic acids with overall yields of 17% and 35% from acetoxyallobetulin, respectively. The reported route makes possible the medium-to-large scale preparation of these pharmacologically important triterpenic acids. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.11.086
• 作为产物：
  描述：

  heterobetulin 、 乙酸酐 生成 1,2,6,6,10,16,17-heptamethyl-20-(acetoxymethyl)pentacyclo[12.8.0.0^2.11.0^5.10.0^15.20]docos-17-en-7-yl acetate
  参考文献：
  名称：

  Dischendorfer; Grillmayer, Monatshefte fur Chemie, 1926, vol. 47, p. 424

  摘要：

  DOI：

文献信息

• Vystrcil,A.; Rihova,E., Collection of Czechoslovak Chemical Communications, 1964, vol. 29, p. 2377 - 2388
  作者：Vystrcil,A.、Rihova,E.

  DOI：——

  日期：——
• Molecular structure of 1,2,6,6,10,16,17-heptamethyl-20-(acetoxymethyl)pentacyclo [12.8.0.02.11.05.10.015.20]docos-17-en-7-yl acetate
  作者：O. B. Kazakova、É. F. Khusnutdinova、N. I. Medvedeva、A. N. Lobov、K. Yu. Suponitskii

  DOI：10.1134/s0022476612050198

  日期：2012.9

  The molecular structure of 3 beta,28-diacetoxy-18 alpha H,19 beta H-ursan-20-en is determined. Compound C34H54O4 II crystallizes in the P2(1)2(1)2(1) chiral space group: a = 8.2721(6) , b = 11.2728(8) , c = 32.559(2) .
• Rihova,E.; Vystrcil,A., Collection of Czechoslovak Chemical Communications, 1966, vol. 31, p. 3163 - 3173
  作者：Rihova,E.、Vystrcil,A.

  DOI：——

  日期：——