(22E,24S)-3α,5-cyclo-26-nor-5α-ergost-22-en-6-one | 379692-21-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: (22E,24S)-3α,5-cyclo-26-nor-5α-ergost-22-en-6-one
• 英文别名: (1S,2R,5R,7R,10S,11S,14R,15R)-2,15-dimethyl-14-[(E,2R,5S)-5-methylhept-3-en-2-yl]pentacyclo[8.7.0.02,7.05,7.011,15]heptadecan-8-one
• CAS: 379692-21-4
• 化学式: C₂₇H₄₂O
• 分子量: 382.63
• InChiKey: FIYBRLVJLXWUJI-FCOHBUFQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (22E,24S)-3α,5-cyclo-26-nor-5α-ergost-22-en-6-one 在 4-甲基苯磺酸吡啶 、 lithium bromide 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 5.0h， 以86.9%的产率得到(22E,24S)-26-nor-5α-ergosta-2,22-dien-6-one
  参考文献：
  名称：

  Synthesis and biological activity of 26-norbrassinolide, 26-norcastasterone and 26-nor-6-deoxocastasterone

  摘要：

  26-Norbrassinolide, identified as a metabolite of brassinolide in cultured cells of the liverwort, Marchantia polymorpha, as well as 26-norcastasterone and 26-nor-6-deoxocastasterone were synthesized. Synthesis of these new brassinosteroids was conducted by employing the orthoester Claisen rearrangement and asymmetric dihydroxylation as key reactions. The modified rice lamina inclination test indicated that these three 26-norbrassinosteroids were less active than their corresponding C-28 brassinosteroids. Growth-promoting activities were also examined by using the brassinosteroid-deficient, dwarf mutant lkb of garden pea (Pisum sativum L.). In this assay, 26-norbrassinolide was as effective as brassinolide and 26-norcastasterone was more effective than castasterone although 26-nor-6-deoxocastasterone was much less effective than 6-deoxocastasterone. Therefore, removal of C-26 of brassinosteroids does not necessarily reduce the biological activity. The role of C-26 removal in Marchantia cells remains unclear. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(01)00213-8
• 作为产物：
  描述：

  ethyl (22E,24R)-3α,5-cyclo-6,6-ethylenedioxy-26-nor-5α-ergost-22-en-27-oate 在 lithium aluminium tetrahydride 、 硫酸 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 为溶剂， 反应 8.0h， 生成 (22E,24S)-3α,5-cyclo-26-nor-5α-ergost-22-en-6-one
  参考文献：
  名称：

  Synthesis and biological activity of 26-norbrassinolide, 26-norcastasterone and 26-nor-6-deoxocastasterone

  摘要：

  26-Norbrassinolide, identified as a metabolite of brassinolide in cultured cells of the liverwort, Marchantia polymorpha, as well as 26-norcastasterone and 26-nor-6-deoxocastasterone were synthesized. Synthesis of these new brassinosteroids was conducted by employing the orthoester Claisen rearrangement and asymmetric dihydroxylation as key reactions. The modified rice lamina inclination test indicated that these three 26-norbrassinosteroids were less active than their corresponding C-28 brassinosteroids. Growth-promoting activities were also examined by using the brassinosteroid-deficient, dwarf mutant lkb of garden pea (Pisum sativum L.). In this assay, 26-norbrassinolide was as effective as brassinolide and 26-norcastasterone was more effective than castasterone although 26-nor-6-deoxocastasterone was much less effective than 6-deoxocastasterone. Therefore, removal of C-26 of brassinosteroids does not necessarily reduce the biological activity. The role of C-26 removal in Marchantia cells remains unclear. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(01)00213-8