5α-cholestan-3β,6β-diol diacetate | 3514-29-2

• 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-cholestan-3β,6β-diol diacetate
• 英文别名: 5α-cholestane-3β,6β-diol diacetate；5α-cholestane-3β,6β-diyl diacetate；3β,6β-diacetoxy-5α-cholestane；3β,6β-diacetoxy-5α-cholestan；5α-cholestanediyl-(3β.6β)-diacetate；(10R)-3c.6c-Diacetoxy-10r.13c-dimethyl-17c-((R)-1.5-dimethyl-hexyl)-(5tH.8cH.9tH.14tH)-hexadecahydro-1H-cyclopenta[a]phenanthren；[(3S,5S,6R,8S,9S,10R,13R,14S,17R)-6-acetyloxy-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
• CAS: 3514-29-2
• 化学式: C₃₁H₅₂O₄
• 分子量: 488.751
• InChiKey: CCNIYQVWQJGGBH-GYJXTMRYSA-N

物化性质

• 熔点：
  137 °C
• 沸点：
  529.4±33.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5α-cholestan-3β,6β-diol diacetate 在 氢氧化钾 、 正丁基锂 、 jones reagent 、 N,N-二乙基环己胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 正己烷 、 丙酮 为溶剂， 反应 22.92h， 生成 6β-methoxymethoxy-3-methylene-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
• 作为产物：
  描述：

  6,β-bromo-4-cholesten-3-one 在 吡啶 、 盐酸 、 溶剂黄146 、 铂 作用下， 生成 5α-cholestan-3β,6β-diol diacetate
  参考文献：
  名称：

  Specialized generalists: constraints on host range in some plusiine caterpillars

  摘要：

  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.

  DOI：

  10.1007/pl00008859

文献信息

• Simultaneously Rapid Deprotection of 3-acyloxy groups and reduction of D-ring ketones (nitrile) of steroids using DIBAL-H/NiCl₂
  作者：Xingbin Wang、Hui Liu、Peiyun Yan、Jinliang Liu、Yan Li、Qian Sun、Cunde Wang

  DOI：10.3184/174751911x13050949941793

  日期：2011.5

  An efficient preparation of hydroxysteroids by a one-pot, simultaneously rapid deprotection of 3-acyloxy groups and reduction of D-ring ketones (nitrile) of steroids using DIBAL-H in the presence of NiCl2 (10 mol %) is described. The attractive features of this procedure for the preparation of the hydroxysteroid derivatives are the mild reaction conditions, short reaction time, excellent yields, clean

  描述了在 NiCl2 (10 mol%) 存在下使用 DIBAL-H 通过一锅法同时快速脱保护 3-酰氧基和还原类固醇的 D 环酮（腈）来有效制备羟基类固醇的方法。这种制备羟基类固醇衍生物的方法的吸引人的特点是反应条件温和、反应时间短、产率高、反应曲线干净和催化剂体系便宜。
• Dissolving metal reduction of esters to alkanes. A method for the deoxygenation of alcohols
  作者：Anthony G. M. Barrett、Christopher R. A. Godfrey、David M. Hollinshead、Panayiotis A. Prokopiou、Derek H. R. Barton、Robin B. Boar、Laurette Joukhadar、James F. McGhie、Satish C. Misra

  DOI：10.1039/p19810001501

  日期：——

  Diverse carboxylic esters have been reduced with dissolving Group 1A metals. Using lithium in ethylamine, sterically hindered esters (RCO2R′) were deoxygenated giving the alkane (R′H) whereas non-hindered esters regenerated the parent alcohol (R′OH). This permitted the selective deoxygenation of diesters. Conversely, potassium–sodium eutectic solubilised with 18-crown-6 in t-butylamine and tetrahydrofuran

  溶解1A族金属可还原各种羧酸酯。使用乙胺中的锂，将位阻酯（RCO 2 R'）脱氧，得到烷烃（R'H），而无阻酯则再生出母体醇（R'OH）。这允许二酯的选择性脱氧。相反，用18-crown-6溶解于叔丁胺和四氢呋喃（THF）中的钾钠共晶可有效地对受阻酯和非受阻酯进行脱氧。在室温下不存在亲核试剂的情况下，羧酸酯基团阴离子的主要反应是脱氧。
• Reductions of steroidal halohydrins and their esters by tri-n.butyltin hydride; some stereospecific 1.2-migrations of acetoxy- or benzoxy-groups
  作者：Sylvestre A. Julia、Robert Lorne

  DOI：10.1016/s0040-4020(01)88052-2

  日期：1986.1

  bearing hydroxy-, acetoxy- or benzoxy-groups in the 3β and 4β or 3β and 6β positions, , , , , , and have been hydrogenolysed with the title reagent to afford the corresponding reduced derivatives. The reduction of 4α-chloro-5β-cholestane-3β, 5-diol 3-benzoate () and 3α-chloro-5α-cholestan-2β-ol acetate gave also the products of simple hydrogenolysis.

  六5α氯和一种5α溴胆甾烷衍生物轴承羟基，乙酰氧基或苯甲酰氧基的基团在3β和4β或3β和6β位置，，，，，和已被氢解，与标题试剂，得到相应的还原导数。4α-氯-5β-胆甾烷-3β，5-二醇3-苯甲酸酯（）和3α-氯-5α-胆甾烷-2β-醇乙酸酯的还原也产生了简单的氢解产物。
• On the deceptive behavior of tri-n-butyltin hydride: In the reduction of acetates of some bromohydrins. A stereospecific radical rearrangement
  作者：Pavel Kočovsk、Ivo Starý、František Tureček

  DOI：10.1016/s0040-4039(00)84300-2

  日期：1986.1

  surprisingly leads to the 6α-acetoxy derivative 8 and not to the expected product 6. Structural requirements of this stereospecific rearrangement are discussed. Isotopic labeling demonstrated that the rearrangement proceeds as a 1,2-shift involving the ether oxygen of the acetoxy group (21 → 22) in contrast to an earlier observation.

  用Bu 3 SnH对乙酸溴代醇7进行自由基氢解令人惊奇地导致6α-乙酰氧基衍生物8而不是预期的产物6。讨论了这种立体有规重排的结构要求。同位素标记表明，与较早的观察结果相反，重排以1,2-转移的方式进行，其中涉及乙酰氧基的醚氧（21→22）。
• Ahmad, M. S.; Raza, S. K.; Kardash, Taufik S., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1989, vol. 28, # 1-11, p. 855 - 857
  作者：Ahmad, M. S.、Raza, S. K.、Kardash, Taufik S.、Ayad, Tariq M.

  DOI：——

  日期：——