5α-cholestane-3β,6β-diol 3-acetate | 4470-73-9

• 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-cholestane-3β,6β-diol 3-acetate
• 英文别名: 6β-Hydroxy-3β-acetoxy-5α-cholestane；5α-cholestane-3β,6β-diol 3-monoacetate；3-β-acetoxy-cholestan-6-β-ol；acetic acid-(6β-hydroxy-5α-cholestanyl-(3β)-ester)；(10R)-6c-Hydroxy-3c-acetoxy-10r.13c-dimethyl-17c-((R)-1.5-dimethyl-hexyl)-(5tH.8cH.9tH.14tH)-hexadecahydro-1H-cyclopenta[a]phenanthren；Essigsaeure-(6β-hydroxy-5α-cholestanyl-(3β)-ester)；3β-Acetoxy-5α-cholestanol-(6β)；[(3S,5S,6R,8S,9S,10R,13R,14S,17R)-6-hydroxy-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: 4470-73-9
• 化学式: C₂₉H₅₀O₃
• 分子量: 446.714
• InChiKey: CKNKAHPLLXYVGQ-SBJPRDOKSA-N

物化性质

• 沸点：
  516.1±33.0 °C(Predicted)
• 密度：
  1.02±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5α-cholestane-3β,6β-diol 3-acetate 在 氢氧化钾 、 jones reagent 作用下， 以 吡啶 、 甲醇 、 氯仿 、 丙酮 为溶剂， 反应 3.17h， 生成 3α-Trifluoroacetoxy-5α-cholestan-6-one
  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：

  3β-acetoxy-5α-bromocholestan-6β-ol 在 chromium(II) acetate 、 2-巯基乙醇 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 生成 5α-cholestane-3β,6β-diol 3-acetate
  参考文献：
  名称：

  Barton,D.H.R. et al., Journal of the Chemical Society. Perkin transactions I, 1979, p. 1159 - 1165

  摘要：

  DOI：

文献信息

• Triphenylbismuth dibromide-iodine: An efficient reagent for the dehydration of alcohols
  作者：Rosa L. Dorta、Ernesto Suárez、Carmen Betancor

  DOI：10.1016/s0040-4039(00)73313-2

  日期：1994.7

  Tertiary and secondary alcohols react under mild conditions with triphenylbismuth dibromide and iodine under an inert atmosphere to give the corresponding most stable alkenes in good yields.

  叔醇和仲醇在惰性气氛下，在温和的条件下与二溴化三苯基铋和碘反应，以良好的收率得到相应的最稳定的烯烃。
• Oxidative cyclization and fragmentation of steroidal alcohols induced by ceric ammonium nitrate
  作者：Venkataraman Balasubramanian、Cecil H. Robinson

  DOI：10.1016/s0040-4039(01)90139-x

  日期：——

  Oxidative cyclizations of steroidal alcohols (1a–1d) using ceric ammonium nitrate (CAN) in aqueous acetonitrile or aqueous acetic acid gave the corresponding cyclic ethers (2a–2d), whereas the tertiary alcohol (4) gave secosteroid (5).

  使用硝酸铈铵（CAN）在乙腈水溶液或乙酸水溶液中对甾体醇（1a-1d）进行氧化环化，得到相应的环状醚（2a-2d），而叔醇（4）则产生甾类甾醇（5）。
• 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。
• Remote functionalization on the steroid β-face: Attack on an angular methyl group, and into the sidechain
  作者：Ronald Breslow、Uday Maitra、Dennis Heyer

  DOI：10.1016/s0040-4039(01)91539-4

  日期：——

  Benzophenonealkanoate esters of 6-β-cholestanes insert photolytically into C-15, C-16, and the C-18 methyl, or into C-23 and C-25 of the sidechain, depending on the length of the attaching chain.

  根据连接链的长度，6-β-胆甾烷的苯甲酮链烷酸酯可光解性插入C-15，C-16和C-18甲基，或侧链的C-23和C-25。
• 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.