5α-cholest-7,9(11)-diene-3β,5,6α-triol-3,6-diacetate | 71831-85-1

• 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: 5α-cholest-7,9(11)-diene-3β,5,6α-triol-3,6-diacetate
• 英文别名: cholesta-7,9(11)-diene-3β,5α,6α-triol 3,6-diacetate；5α-cholesta-7,9(11)-diene-3β,5,6α-triol 3,6-diacetate；3β,6α-Diacetoxy-5α-cholesta-7,9(11)-dien-5α-ol；[(3S,5R,6S,10R,13R,14R,17R)-6-acetyloxy-5-hydroxy-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,3,4,6,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-yl] acetate
• CAS: 71831-85-1
• 化学式: C₃₁H₄₈O₅
• 分子量: 500.719
• InChiKey: MPVWWXRKLVQXDR-NERDSGEYSA-N

物化性质

• 沸点：
  570.7±50.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  36
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5α-cholest-7,9(11)-diene-3β,5,6α-triol-3,6-diacetate 在 platinum(IV) oxide 盐酸 、 氢气 、 三乙胺 作用下， 以 甲醇 、 乙醚 为溶剂， 生成 3β,6α-Diacetoxy-5α,17β(H)-cholest-14-en-5α-ol
  参考文献：
  名称：

  Synthesis of 14.beta.,17.beta.(H)-cholest-5-en-3.beta.-ol

  摘要：

  DOI：

  10.1021/jo00394a056
• 作为产物：
  描述：

  5α,6α-epoxycholest-7-en-3β-ol 在 吡啶 、 氢氧化钾 、 mercury(II) diacetate 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 48.0h， 生成 5α-cholest-7,9(11)-diene-3β,5,6α-triol-3,6-diacetate
  参考文献：
  名称：

  合成硬皮甾醇，两种具有细胞毒性的多氧化海绵类固醇

  摘要：

  据报道，两种细胞毒性海洋类固醇硬皮甾醇A和B的合成。

  DOI：

  10.1016/0040-4039(96)00932-x

文献信息

• Pyridine-idnduced dishielding of 4-methylene protons for the determination of C-6 stereochemistry of sterols having a 5.ALPHA.,6-diol moiety. Revision of the C-6 stereochemistry of marine sterol isolated from a sponge, Dysidea sp.
  作者：YOSHINORI FUJIMOTO、TAKETOSHI YAMADA、NOBUO IKEKAWA

  DOI：10.1248/cpb.33.3129

  日期：——

  The utility of the proton nuclear magnetic resonance method involving pyridine-induced deshielding was demonstrated for stereochemical assignment at the C-6 position of sterols having a 5α, 6ζ-diol moiety. Thus, the 4α-hydrogen resonance of 6α-isomers such as cholest-7-ene-3β, 5α, 6α-triol (8) is observed at ca. 3.0 ppm, whereas the 4β-hydrogen resonance of 6β-isomers such as cholest-7-ene-3β, 5α, 6β-triol (10) is observed at ca. 3.0 ppm. This method was applied to a marine sterol (4) isolated from a sponge, Dysidea sp., and it was concluded that the structure should be revised to the 6α-isomer (5) rather than the reported 6β-isomer (4).

  通过吡啶诱导去屏蔽的质子核磁共振方法，展示了在具有5α, 6β-二醇基团的甾醇C-6位的立体化学分配中的应用。因此，像胆甾-7-烯-3β, 5α, 6α-三醇（8）这样的6α-异构体的4α-氢共振在大约3.0 ppm处被观察到，而像胆甾-7-烯-3β, 5α, 6β-三醇（10）这样的6β-异构体的4β-氢共振同样在大约3.0 ppm处被观察到。该方法被应用于从海绵Dysidea sp.分离出的海洋甾醇（4），并得出结论，结构应修订为6α-异构体（5），而非报告的6β-异构体（4）。
• Synthesis of the marine epoxy sterol 9α,11α-epoxy-5α-cholest-7-ene-3β,5,6β-triol
  作者：Anna Migliuolo、Giacomo Notaro、Vincenzo Piccialli、Donato Sica

  DOI：10.1016/0039-128x(91)90066-5

  日期：1991.3

  oxidation with manganese dioxide and epoxidation with m-chloroper-benzoic acid, afforded 9 alpha,11 alpha-epoxy-3 beta,5-dihydroxy-5 alpha-cholest-7-en-6-one (5). Reduction of 5 with lithium aluminum hydride gave the desired compound 1. The structures of all synthetic intermediates were confirmed by 1H and 13C nuclear magnetic resonance (NMR) spectroscopy. A reassignment of resonances for carbons 1

  9 alpha，11 alpha-epoxy-5 alpha-cholest-7-ene-3 beta，5,6 beta-triol（1）的合成，这是一种高度氧化的海洋甾醇，在核中含有9,11-环氧部分，描述。环氧甾醇1由cholesta-5,7-dien-3 beta-ol合成。用间氯过苯甲酸氧化该甾醇，然后水解和乙酰化，得到5α-胆甾-7-烯-3β，5，6-α-三醇3，6-二乙酸酯（2）。用乙酸汞将二乙酸酯2脱氢，然后用二氧化锰氧化，再用间氯过苯甲酸环氧化，得到9 alpha，11 alpha-epoxy-3 beta，5-dihydroxy-5 alpha-cholest-7-en-6-一（5）。用氢化铝锂还原5得到所需的化合物1。所有合成中间体的结构通过1 H和13 C核磁共振（NMR）光谱法确认。
• Studies towards the synthesis of polyoxygenated steroids. Reaction of 7,9(11)-diene steroids with RuO4.
  作者：Giacomo Notaro、Vincenzo Piccialli、Donato Sica、Dina Smaldone

  DOI：10.1016/s0040-4020(01)85020-1

  日期：1994.4

  In order to find an entry to C-ring oxygenated steroids, the reaction of ruthenium tetroxide with some Delta(7,9(11))-sterols gas been explored. The reaction has been performed both at -70 degrees C and room temperature using an equimolecular amount of the oxidant and acetone-water as solvent system in the absence of a cooxidant. The change in the temperature conditions moderately affects the yields of the reaction products. When 3 beta,6 alpha- and 3 beta,6 beta-diacetoxy-Delta(7,9(11))-sterols were used the diene system was predominantly attacked at the 9(11)-double bond from the alpha-face of the molecule giving Delta(7)-9 alpha-hydroxy-11-keto- and Delta(7)-9 alpha,11 alpha-dihydroxy-sterols. RuO4 oxidation of cholesta-7,9(11)-dien-3 beta-yl acetate, yielded, in addition to the above oxidation products, minor amounts of three related C-7,C-11 oxigenated 8 alpha,9 alpha-epoxysterols, arising from the oxidation of both double bonds of the diene system. These results, that in part parallel those we recently found on RuO4 oxidation of trisubstituted [Delta(4), Delta(5) and Delta(7)] steroidal alkenes, shed further light on the reactivity of this oxidizing agent which, neverthless, seems far from being completely understood. In addition, our procedure furnishes a reliable route to Delta(7)-9 alpha,11 beta-dihydroxysterols via LiAlH4 reduction of the 11-keto group.