3β-methoxy-5α-cholestan-6-one | 5837-39-8

• 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: 3β-methoxy-5α-cholestan-6-one
• 英文别名: 5alpha-Cholestan-6-one, 3beta-methoxy-；(3S,5S,8S,9S,10R,13R,14S,17R)-3-methoxy-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,3,4,5,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-6-one
• CAS: 5837-39-8
• 化学式: C₂₈H₄₈O₂
• 分子量: 416.688
• InChiKey: GGNMCEMUZBBANL-SHAKVYGTSA-N

物化性质

• 沸点：
  490.7±28.0 °C(Predicted)
• 密度：
  0.99±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3β-methoxy-5α-cholestan-6-one 在 lithium aluminium tetrahydride 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 生成
  参考文献：
  名称：

  Remote functionalization on the steroid β-face: Attack on carbon-15

  摘要：

  DOI：

  10.1016/s0040-4039(00)80090-8
• 作为产物：
  描述：

  3β-methoxy-6-nitrocholest-5-ene 在 溶剂黄146 、 锌 作用下， 生成 3β-methoxy-5α-cholestan-6-one
  参考文献：
  名称：

  Estimation of the Water Resources Potential in the Island System of the Aegean Archipelago, Greece

  摘要：

  The present paper tries to estimate the surface water resources potential in some of the major Aegean islands in an effort to provide a means for the continuous development of the region, and, by extension, for similar areas around the world The islands have to confront the challenge of surviving in a semiarid environment under the constraints of uneven water resources distribution both in space and time. In addition to these, tourism development, industrialization and highly water consumptive life styles have exacerbated perennial problems in water resources and water resources management. The framework of the present effort has a two-prong emphasis. In the first part, a simulation model is presented, which tries to estimate the potential surface runoff under physical, structural organizational, and institutional constraints. The methodology and the premises' of the simulation process are delineated In the second part, the results of the model application in distinct cases are demarcated. The final product, namely the model and the resulting runoff coefficients, are presented in the form of a standard, which may provide practitioners in the field as well as decisionmakers the means for an initial reference in pertinent developmental efforts. Finally, the conclusions and recommendations raise the question of ecosystem resilience and point towards the urgent and continuous need for the application of integrated-water resources management principles.

  DOI：

  10.1080/02508060208686998

文献信息

• Reaction of nitro-alkenes with iodotrimethylsilane: a new method for the conversion of vinyl nitrosteroids to ketosteroids
  作者：Gireesh M. Singhal、Nalin B. Das、Ram P. Sharma

  DOI：10.1039/c39890001470

  日期：——

  Iodotrimethylsilane generated in situ from chlorotrimethylsilane and sodium iodide effects the reduction of nitro-alkenes (1a–e) and (5) at –5 to 0 °C to furnish the ketones (2a–e) and (6) respectively as the major products.

  由氯代三甲基硅烷和碘化钠原位生成的碘代三甲基硅烷可在–5至0°C下还原硝基烯烃（1a – e）和（5），从而分别提供酮（2a – e）和（6）作为主要产物。
• Synthesis of 5.ALPHA.-cholestan-6-one derivatives with some substituents at the C-1, C-2, or C-3 position.
  作者：SUGURU TAKATSUTO、NOBUO IKEKAWA

  DOI：10.1248/cpb.35.986

  日期：——

  In order to investigate the regioselectivity of Baeyer-Villiger oxidation, thirty 5α-cholestan-6- one derivatives with various substituents (methyl, hydrogen, acetoxymethyl, methoxy, acetyloxy, benzoyloxy, trifluoroacetyloxy, p-toluenesulfonyloxy) at the C-1, C-2, or C-3 position were synthesized from cholesterol. The 6-oxo functional group of 5α-cholestan-6-one derivatives was introduced via hydroboration. The 3β-derivatives were readily obtained by using the native 3β- hydroxyl group of cholesterol. The 3α-isomers were obtained by inversion of the configuration of the 3β-tosylate 24 with tetra-n-butylammonium acetate in refluxing 2-butanone. The 2β-isomers were derived from the 2-ene 43 by bromohydrination, LiAlH4 reduction, and esterification. The 2β- to 2α-hydroxyl group inversion was achieved by Birch reduction of the 2-oxo steroid 51. The 1α-derivatives were derived from the known 6β-acetoxy- 1 α-hydroxy-5α-cholest-2-ene (57).

  为了研究拜耳-维利格氧化的区域选择性，我们从胆固醇合成了30种具有不同取代基（甲基、氢、乙酰氧甲基、甲氧基、乙酰氧基、苯甲酰氧基、三氟乙酰氧基、对甲苯磺酰氧基）在C-1、C-2或C-3位置的5α-胆甾烷-6-酮衍生物。通过氢硼化反应引入5α-胆甾烷-6-酮衍生物的6-氧功能团。通过使用胆固醇天然的3β-羟基，可以轻松得到3β-衍生物。通过在回流2-丁酮中使用四正丁基铵醋酸盐，将3β-甲苯磺酸酯24的构型反转得到3α-异构体。2β-异构体来自2-烯43通过溴氢化、LiAlH4还原和酯化反应得到。2β-到2α-羟基的反转通过2-氧甾体51的伯奇还原实现。1α-衍生物来自已知的6β-乙酰氧基-1α-羟基-5α-胆甾-2-烯（57）。
• Remote substituent effect on the regioselectivity in the baeyer-villiger oxidation of 5α-cholestan-6-one derivatives
  作者：Suguru Takatsuto、Nobuo Ikekawa

  DOI：10.1016/s0040-4039(00)81564-6

  日期：——

  The regioselectivity in the Baeyer-Villiger oxidation of 5α-cholestan-6-one derivatives was markedly affected by the substituents at C-1, 2 or 3 position which were located at γ or δ position from the reaction center c-6.

  5α-胆甾烷-6-一衍生物在Baeyer-Villiger氧化中的区域选择性受到位于距反应中心c-6的γ或δ位置的C-1、2或3位取代基的显着影响。
• Aspects of the Reduction of Double Bonds Using Cob (I)alamin as Catalys
  作者：Albert Fischli

  DOI：10.1002/hlca.19820650839

  日期：1982.12.15

  The olefinic system in 3β-methoxy-4-cholesten-6 a-ol (2) is reduced using cob (I)alamin (1(I); see Scheme 1) as catalyst, aqueous acetic acid as solvent and metallic zinc as electron source (cf. Schemes 2 and 3). Experimental evidence for an attack of 1(I) on both faces of the double bond is presented. By the same catalyst (1 R)-10, 10-dimethyl-2-pinene- 10-carbonitrile (9) is first transformed to

  在烯属系统3β甲氧基-4-胆甾-6-一个醇（2）使用芯被降低（I）胺素（1（我）;参见路线1）作为催化剂，乙酸水溶液作为溶剂和金属锌作为电子来源（请参阅方案2和3）。提出了在双键的两个面上攻1（I）的实验证据。通过相同的催化剂（1 R）-10，首先将10-二甲基-2-pine烯-10-腈（9）转化为甲基萘衍生物11（参见方案4和5）。然后在开环之后是11中的二取代的烯烃系统的快速饱和，并且最终剩余的双键在缓慢的反应中被还原。顺式构型的饱和薄荷烷衍生物16是主要的终产物（16 / 17 ≈10：1）。
• 6-Polyaminosteroid Squalamine Analogues Display Antibacterial Activity against Resistant Pathogens
  作者：Delphine Vergoz、Flore Nilly、Florie Desriac、Magalie Barreau、Antoine Géry、Charlie Lepetit、François Sichel、Katy Jeannot、Jean-Christophe Giard、David Garon、Sylvie Chevalier、Cécile Muller、Emmanuelle Dé、Jean Michel Brunel

  DOI：10.3390/ijms24108568

  日期：——

  and 4n, and showed an additive or synergistic effect with vancomycin or oxacillin. On the other hand, the derivative 4f, which carries a spermine moiety like that of the natural trodusquemine molecule, was found to be the most active derivative against all the resistant Gram-negative bacteria tested, with an MIC value of 16 µg/mL. Our results suggest that 6-polyaminosteroid analogues of squalamine are

  合成了一系列角鲨胺的 6-聚氨基类固醇类似物，产量适中，并评估了它们对敏感和耐药革兰氏阳性菌（耐万古霉素屎肠球菌和耐甲氧西林金黄色葡萄球菌）和革兰氏阴性菌（碳青霉烯耐药的鲍曼不动杆菌和铜绿假单胞菌）菌株。对于最有效的化合物 4k 和 4n，对革兰氏阳性菌的最低抑制浓度范围为 4 至 16 µg/mL，并且显示出与万古霉素或苯唑西林的相加或协同作用。另一方面，衍生物 4f 带有类似于天然 trodusquemine 分子的精胺部分，被发现是对所有测试的耐药革兰氏阴性菌最活跃的衍生物，MIC 值为 16 µg/mL。我们的结果表明，角鲨胺的 6-聚氨基类固醇类似物是革兰氏阳性细菌感染治疗的有趣候选物，也是对抗革兰氏阴性细菌耐药性的有效佐剂。