3-((4R,4aR,4bR,6aR,7S,8S,10aR,10bR,12aR)-3,3,7,10a,10b-pentamethyl-13-oxo-8-(prop-1-en-2-yl)hexadecahydro-1H-4,12a-(epoxymethano)chrysen-7-yl)propanenitrile | 76449-16-6

• 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: 3-((4R,4aR,4bR,6aR,7S,8S,10aR,10bR,12aR)-3,3,7,10a,10b-pentamethyl-13-oxo-8-(prop-1-en-2-yl)hexadecahydro-1H-4,12a-(epoxymethano)chrysen-7-yl)propanenitrile
• CAS: 76449-16-6
• 化学式: C₃₀H₄₅NO₂
• 分子量: 451.693
• InChiKey: ZURXZYDGISHVJZ-VBZNOLKWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.46
• 重原子数：
  33.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  50.09
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-((4R,4aR,4bR,6aR,7S,8S,10aR,10bR,12aR)-3,3,7,10a,10b-pentamethyl-13-oxo-8-(prop-1-en-2-yl)hexadecahydro-1H-4,12a-(epoxymethano)chrysen-7-yl)propanenitrile 在 臭氧 作用下， 以 二氯甲烷 为溶剂， 生成 3-nitrilo-19β,28-epoxy-4,28-dioxo-3,4-seco-23-noroleanane
  参考文献：
  名称：

  Synthesis of terminal acetylenes using POCl3 in pyridine as applied to natural triterpenoids

  摘要：

  Four new triterpenoids with alkyne moieties have been synthesized by the proposed procedure; among them, 3 beta,28-dihydroxy-29-norlup-20(30)-yne has demonstrated antiviral activity against papilloma virus and HCV replicon.

  DOI：

  10.1016/j.mencom.2010.06.018
• 作为产物：
  描述：

  白桦脂醇 在 Jones reagent 、 甲酸 、 盐酸羟胺 、 对甲苯磺酰氯 作用下， 以 吡啶 、 乙醇 为溶剂， 生成 3-((4R,4aR,4bR,6aR,7S,8S,10aR,10bR,12aR)-3,3,7,10a,10b-pentamethyl-13-oxo-8-(prop-1-en-2-yl)hexadecahydro-1H-4,12a-(epoxymethano)chrysen-7-yl)propanenitrile
  参考文献：
  名称：

  Synthesis of terminal acetylenes using POCl3 in pyridine as applied to natural triterpenoids

  摘要：

  Four new triterpenoids with alkyne moieties have been synthesized by the proposed procedure; among them, 3 beta,28-dihydroxy-29-norlup-20(30)-yne has demonstrated antiviral activity against papilloma virus and HCV replicon.

  DOI：

  10.1016/j.mencom.2010.06.018

文献信息

• Synthesis, Cytotoxicity, and α-glucosidase Inhibitory Activity of Triterpenic and Sitosterol Tetrazole Derivatives
  作者：Anastasiya V. Petrova、Alexander I. Poptsov、Ha Nguyen Thi Thu、Nguyen Van Tuyen、Elmira F. Khusnutdinova、Denis A. Babkov、Oxana B. Kazakova

  DOI：10.1007/s10593-021-03001-6

  日期：2021.9

  fragments at positions C-2, C-3, and C-12 have been synthesized by 1,3-dipolar cycloaddition of nitriles to sodium azide. The structure of the obtained compounds was confirmed by NMR spectroscopy, including two-dimensional correlation experiments, and mass spectrometry. It was found that such steric factors as the presence of 23,24-gem-dimethyl groups or a second cyanoethyl group at position C-2 affect

  1,3 合成了一系列新的三萜和谷甾醇衍生物，在 C-2、C-3 和 C-12 位含有 1,2,3,4-(tetrazol-5-yl)乙氧基和-乙氧基亚胺片段。 -腈与叠氮化钠的偶极环加成反应。所得化合物的结构经核磁共振波谱法，包括二维相关实验和质谱法证实。发现诸如23,24-偕-二甲基或C-2位的第二氰乙基的存在等空间因素影响反应产物的产率。体外研究表明，甲基 2-[2-(1 Н- tetrazol-5-yl)]-2,4-seco-3-norlupa-4(23),20(29)-dien-28-oate 和24-乙基-3-[2-(1 Н-tetrazol-5-yl)ethoxy]cholestan-5-ene 分别具有最高的抗癌活性和 α-葡萄糖苷酶抑制活性。