6β-hydroxy-3β-p-toluenesulfonyloxy-5α-cholestane | 15223-09-3

• 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: 6β-hydroxy-3β-p-toluenesulfonyloxy-5α-cholestane
• 英文别名: 3β-(toluene-4-sulfonyloxy)-5α-cholestan-6β-ol；3β-(Toluol-4-sulfonyloxy)-5α-cholestan-6β-ol；3β-(Toluol-sulfonyl-(4)-oxy)-5α-cholestanol-(6β)
• CAS: 15223-09-3
• 化学式: C₃₄H₅₄O₄S
• 分子量: 558.866
• InChiKey: WQEDEZRPTFPKJD-RIBREPMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.16
• 重原子数：
  39.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  63.6
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  6β-hydroxy-3β-p-toluenesulfonyloxy-5α-cholestane 在 吡啶 、 三氯氧磷 作用下， 生成 3α-Thiocyanato-cholesten-(5)
  参考文献：
  名称：

  Bourdon, Bulletin de la Societe Chimique de France, 1958, p. 1117

  摘要：

  DOI：
• 作为产物：
  描述：

  胆固醇 在 盐酸 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 反应 2.0h， 生成 6β-hydroxy-3β-p-toluenesulfonyloxy-5α-cholestane
  参考文献：
  名称：

  Synthesis of 5.ALPHA.-cholestan-6-one derivatives with some substituents at the C-1, C-2, or C-3 position.

  摘要：

  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）。

  DOI：

  10.1248/cpb.35.986

文献信息

• Conformational free energy differences in steroids. Part VI. Intramolecular electrostatic interactions in 3-azidocholestan-6-ones: conformational preference of the azido-group
  作者：D. Neville Jones、K. J. Wyse、D. E. Kime

  DOI：10.1039/j39710002763

  日期：——

  Equilibrations of 3α- and 3β-azido-5α-cholestan-6-ones with their 5β-isomers were influenced by intramolecular electrostatic interactions between the azide and ketone groups. Calculated values for these interactions were in reasonable accord with the experimental findings. N.m.r. spectroscopic examination of cyclohexyl azide at –80° in carbon disulphide, [2H4]methanol, and [2H8]toluene provided a value

  3 Equilibrations α -和3β叠氮基-5- α与其5β异构体-胆甾-6-酮是由叠氮化物和酮基之间的分子内的静电相互作用的影响。这些相互作用的计算值与实验结果合理地吻合。在二硫化碳，[ 2 H 4 ]甲醇和[ 2 H 8 ]甲苯中于–80°进行环己基叠氮化物的Nmr光谱检查，可为叠氮基的构象偏爱度提供一个值。对于2 M，最准确的数字是0·80±0·06 kcal mol –1-二硫化碳溶液。讨论了叠氮基，异氰酸根基和异硫氰酸根基的构象偏好之间的差异。
• Specialized generalists: constraints on host range in some plusiine caterpillars
  作者：R. Tune、D. E. Dussourd

  DOI：10.1007/pl00008859

  日期：2000.6.16

  Insects that feed on plants with secretory canals often cut trenches across leaves, thereby depressurizing the canals and eliminating exudation at their distal feeding site. We compared the trenching ability of three species of polyphagous plusiines (Lepidoptera: Noctuidae) and tested if trenching scores correlate with larval growth. The three plusiines (Trichoplusia ni, Pseudoplusia includens, and Rachiplusia oil) were each tested on prickly lettuce, Lactuca serriola (Asteraceae), which has latex canals, and on Italian parsley, Petroselinum crispum (Apiaceae) with oil ducts. To ascertain how secretory canals affect performance, larvae were tested on intact leaves and on excised leaves with depleted canals. T. ni larvae cut trenches in both plant species, whereas P. includens only trenched prickly lettuce and R. ou only trenched Italian parsley. Intact leaves of Italian parsley were acceptable to all three species. Trenching varied in T. ni and R. ou, but did not correlate significantly with larval growth. In contrast, trenching was required for feeding on intact prickly lettuce. Final-instar T. ni all cut trenches and developed rapidly. P. includens varied in trenching and performance; their trenching scores correlated with growth. R. ou larvae did not trench or feed even though most R. oil on intact Italian parsley cut at least partial trenches. All three plusiine species developed rapidly on excised leaves of both plant species, documenting the suitability of these plants when canals are inactivated. Our results: document the efficacy of latex canals as a plant defense and suggest that trenching ability alone does not permit feeding. Larvae must also recognize the need to trench and must tolerate deterrent exudates during the trenching procedure.
• Steroids and walden inversion. Part XII. The epimeric 3-cholesterylacetic and 3-cholestanylacetic acids
  作者：C. W. Shoppee、R. J. Stephenson

  DOI：10.1039/jr9540002230

  日期：——
• Pierce et al., Journal of the Chemical Society, 1955, p. 694,701
  作者：Pierce et al.

  DOI：——

  日期：——
• Shoppee et al., Journal of the Chemical Society, 1956, p. 4817,4820
  作者：Shoppee et al.

  DOI：——

  日期：——