ethyl (22E)-3β-hydroxy-21-norchola-5,22-dien-24-oate | 882051-91-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl (22E)-3β-hydroxy-21-norchola-5,22-dien-24-oate
• CAS: 882051-91-4
• 化学式: C₂₅H₃₈O₃
• 分子量: 386.575
• InChiKey: DAKARTSQYPJRNM-MGYMLTCESA-N

物化性质

• 沸点：
  496.8±18.0 °C(predicted)
• 密度：
  1.09±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.44
• 重原子数：
  28.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  ethyl (22E)-3β-hydroxy-21-norchola-5,22-dien-24-oate 在 chromium(VI) oxide 、 4-二甲氨基吡啶 、 硫酸 、 potassium hydrogencarbonate 、 三乙胺 作用下， 以 二氯甲烷 、 水 、 丙酮 为溶剂， 生成 ethyl (22E)-21-nor-5α-chola-2,22-dien-24-oate
  参考文献：
  名称：

  Synthesis of 26,27-bisnorcastasterone analogs and analysis of conformation–activity relationship for brassinolide-like activity

  摘要：

  Three castasterone (CS) derivatives with varied side-chain moieties, 26,27-bisnorcastasterone (20S-bisilorCS), 20-epi-26,27-bisnorcastastcrone (20R-bisnorCS), and 21,26,27-trisnorcastasterone (trisnorCS), were synthesized stereoselectively from either stigmasterol or dehydroisoandrosterone. The 50% effective doses (ED50, nmol/plant) in the concentration-response Curve for brassinolide-like activity in the rice lamina inclination assay were determined to be 0.020 nmol (pED(50) = 10.7) for 20S-bisnorCS, 3.2 nmol (pED50 = 8.5) for 20R-bisnorCS, and 2.0 nmol (pED50 = 8.7) for trisnorCS. An analog containing an ester linkage between the steroid and the side-chain moiety of 20S-bisnorCS was also synthesized and its activity was evaluated to be 3.2 nmol (pED50 = 8.5), being equipotent to 20R-bisnorCS and trisnorCS. The activity of 20S-bisnorCS was 1/40 that of CS. The conformation analysis was conducted using a systematic search, showing that the activity decreases with an increase in the degree of freedom of the side chain of the steroidal skeleton. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.10.024
• 作为产物：
  描述：

  在 4-甲基苯磺酸吡啶 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以3.93 g的产率得到ethyl (22E)-3β-hydroxy-21-norchola-5,22-dien-24-oate
  参考文献：
  名称：

  Synthesis of 26,27-bisnorcastasterone analogs and analysis of conformation–activity relationship for brassinolide-like activity

  摘要：

  Three castasterone (CS) derivatives with varied side-chain moieties, 26,27-bisnorcastasterone (20S-bisilorCS), 20-epi-26,27-bisnorcastastcrone (20R-bisnorCS), and 21,26,27-trisnorcastasterone (trisnorCS), were synthesized stereoselectively from either stigmasterol or dehydroisoandrosterone. The 50% effective doses (ED50, nmol/plant) in the concentration-response Curve for brassinolide-like activity in the rice lamina inclination assay were determined to be 0.020 nmol (pED(50) = 10.7) for 20S-bisnorCS, 3.2 nmol (pED50 = 8.5) for 20R-bisnorCS, and 2.0 nmol (pED50 = 8.7) for trisnorCS. An analog containing an ester linkage between the steroid and the side-chain moiety of 20S-bisnorCS was also synthesized and its activity was evaluated to be 3.2 nmol (pED50 = 8.5), being equipotent to 20R-bisnorCS and trisnorCS. The activity of 20S-bisnorCS was 1/40 that of CS. The conformation analysis was conducted using a systematic search, showing that the activity decreases with an increase in the degree of freedom of the side chain of the steroidal skeleton. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.10.024