(22E,24S)-3β-bromo-5α-stigmasta-22-en-6-one | 92804-65-4

• 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)-3β-bromo-5α-stigmasta-22-en-6-one
• 英文别名: 3β-bromo-24S-ethyl-5α-cholest-22-en-6-one；(22E)-3β-bromo-5α-stigmasta-22-en-6-one；(22E)-3β-bromo-5α-stigmast-22-en-6-one；(3S,5S,8S,9S,10R,13R,14S,17R)-3-bromo-17-[(E,2R,5S)-5-ethyl-6-methylhept-3-en-2-yl]-10,13-dimethyl-1,2,3,4,5,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-6-one
• CAS: 92804-65-4
• 化学式: C₂₉H₄₇BrO
• 分子量: 491.596
• InChiKey: BSDSILFTOWYFHA-GRPUIZNGSA-N

物化性质

• 沸点：
  525.1±33.0 °C(Predicted)
• 密度：
  1.099±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.46
• 重原子数：
  31.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (22E,24S)-3β-bromo-5α-stigmasta-22-en-6-one 在 lithium carbonate 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 生成 22S,23S-epoxy-24S-ethyl-5α-cholest-2-en-6-one
  参考文献：
  名称：

  Akhrem, A. A.; Lakhvich, F. A.; Khripach, V. A., Journal of Organic Chemistry USSR (English Translation), 1987, vol. 23, # 4, p. 686 - 692

  摘要：

  DOI：
• 作为产物：
  描述：

  (22E)-3β-acetoxy-5β,6β-epoxystigmast-22-ene 在 吡啶 、 咪唑 、 三氯化铝 、 四丁基氟化铵 、 pyridinium chlorochromate 、 lithium bromide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 38.33h， 生成 (22E,24S)-3β-bromo-5α-stigmasta-22-en-6-one
  参考文献：
  名称：

  Synthesis and bioactivity evaluation of brassinosteroid analogs

  摘要：

  Four new analogs of 28-homocastasterone have been synthesized and completely characterized for the first time from stigmasterol. (22R,23R,24S)-3 beta-acetoxy-22,23-dihydroxy-5 alpha-stigmastan-6-one (17), (22R,23R,24S)-3 beta-bromo-22,23-dihydroxy-5 alpha-stigmastan-6-one (18), (22R,23R,24S)-3 beta-acetoxy-5,22,23-trihydroxy-5 alpha-stigmastan-6-one (20), and (22R,23R,24S)-3 beta-bromo-5,22,23-trihydroxy-5 alpha-stigmastan-6-one (21), were obtained through a synthetic route based on regioselective Delta(5) epoxidation. Compounds 17 and 18, bearing a 5 alpha H moiety, were prepared through a reductive opening of the 5 beta,6 beta epoxy precursor, and compounds 20 and 21, analogs with a 5 alpha OH moiety were obtained by hydrolytic opening of a mixture of 5 alpha,6 alpha and 5 beta,6 beta epoxy precursors. Known compounds 19 and 22 were also obtained following the described synthetic routes, respectively. The new compounds were tested with the traditional auxin-like bioassay for brassinosteroids with 19 and 22 as standards. All compounds were comparatively evaluated for their inhibitory effect on the replication of DNA (HSV-1) virus. (C) 2000 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(00)00093-3

文献信息

• Synthesis and preliminary evaluation of dimeric-28-homobrassinosteroids for plant growth regulators
  作者：Waya S. Phutdhawong、Wanwikar Ruensamran、Weerachai Phutdhawong

  DOI：10.1016/j.steroids.2016.08.016

  日期：2016.12

  Preparation of synthetic analogues of 28-homobrassinosteroids is reported. Also, the addition of the 28-homocastasterone at the C6 carbonyl group via allyl Gringard reagent followed by olefin cross metathesis resulted in dimeric analogues. Rice lamina inclination assay showed that the replacement of the C6 carbonyl group by 6α-allyl and 6β hydroxyl groups led to a decrease in bioactivity, whereas the

  报道了 28-高油菜素类固醇的合成类似物的制备。此外，通过烯丙基 Gringard 试剂在 C6 羰基上添加 28-高卡斯卡酮，然后进行烯烃交叉复分解，产生二聚体类似物。水稻叶片倾斜试验表明，C6 羰基被 6α-烯丙基和 6β 羟基取代导致生物活性降低，而二聚体类似物与 28-同种卡甾酮相比显示出降低但显着的生物活性。
• Akhrem, A. A.; Lakhvich, F. A.; Khripach, V. A., Doklady Chemistry, 1985, vol. 283, p. 187 - 189
  作者：Akhrem, A. A.、Lakhvich, F. A.、Khripach, V. A.、Kovganko, N. V.、Zhabinskii, V. N.

  DOI：——

  日期：——
• Akhrem, A. A.; Lakvich, F. A.; Khripach, V. A., Doklady Chemistry, 1984, vol. 275, p. 126 - 128
  作者：Akhrem, A. A.、Lakvich, F. A.、Khripach, V. A.、Zhabinskii, V. N.、Kovganko, N. V.

  DOI：——

  日期：——
• Takatsuto, Suguru; Kobayashi, Kiyomi; Watanabe, Tsuyoshi, Agricultural and Biological Chemistry, 1988, vol. 52, # 12, p. 3217 - 3218
  作者：Takatsuto, Suguru、Kobayashi, Kiyomi、Watanabe, Tsuyoshi、Kuriyama, Hiroki、Furuse, Tokuo

  DOI：——

  日期：——
• TAKATSUTO, SUGURU;KOBAYASHI, KIYOMI;WATANABE, TSUYOSHI;KURIYAMA, HIROKI;F+, AGR. AND BIOL. CHEM., 52,(1988) N2, C. 3217-3218
  作者：TAKATSUTO, SUGURU、KOBAYASHI, KIYOMI、WATANABE, TSUYOSHI、KURIYAMA, HIROKI、F+

  DOI：——

  日期：——