3,5?二羟基胆甾-6-酮 | 13027-33-3

• 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
• 中文名称: 3,5?二羟基胆甾-6-酮
• 英文名称: 3β,5-dihydroxy-5α-cholestan-6-one
• 英文别名: 3β,5α-dihydroxycholestan-6-one；cholestan-3β,5α,6-one；cholesten-3β,5α-diol-6-one；cholestan-3β,5α-diol-6-one；5α-hydroxy-6-ketocholesterol；6-oxo-cholestane-3β,5α-diol；6-oxocholestane-5α,3β-diol；6-keto-5α-hydroxycholestanol；6-keto-5α-hydroxycholesterol；oncosterone；3β.5-Dihydroxy-5α-cholestanon-(6)；3β,5-Dihydroxy-5α-cholestan-6-on；cholestane-3-β, 5-αdiol-6-one；3,5-dihydroxycholestan-6-one；Yakkasterone；(3S,5R,8S,9S,10R,13R,14S,17R)-3,5-dihydroxy-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-6-one
• CAS: 13027-33-3
• 化学式: C₂₇H₄₆O₃
• 分子量: 418.66
• InChiKey: SJZZRXMQSAXCFD-ZCBMJONGSA-N

物化性质

• 熔点：
  234 °C
• 沸点：
  528.9±45.0 °C(Predicted)
• 密度：
  1.061±0.06 g/cm3(Predicted)
• 溶解度：
  DMF：20mg/mL； DMSO：0.5mg/mL；乙醇：5mg/mL

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,5?二羟基胆甾-6-酮 在 吡啶 、 三氟化硼乙醚 、 溴 、 溶剂黄146 作用下， 生成 3β-acetoxy-7α-bromo-5-hydroxy-5α-cholestan-6-one
  参考文献：
  名称：

  Selective Oxidation with N-Bromosuccinimide. II. Cholestane-3β,5α,6β-triol

  摘要：

  DOI：

  10.1021/ja01180a016
• 作为产物：
  描述：

  cholesterol 在 N-溴代丁二酰亚胺(NBS) 、 溶剂黄146 、 丙酮 作用下， 生成 3,5?二羟基胆甾-6-酮
  参考文献：
  名称：

  Selective Oxidation with N-Bromosuccinimide. II. Cholestane-3β,5α,6β-triol

  摘要：

  DOI：

  10.1021/ja01180a016

文献信息

• A mild oxidizing reagent for alcohols and 1,2-diols: o-iodoxybenzoic acid (IBX) in DMSO
  作者：Marco Frigerio、Marco Santagostino

  DOI：10.1016/0040-4039(94)80038-3

  日期：1994.10

  o-Iodoxybenzoic acid (IBX) smoothly oxidizes primary and secondary alcohols to aldehydes and ketones, respectively. 1,2-Diols are converted to α-ketols or α-diketones without any oxidative cleavage of the glycol CC bond. IBX oxidations are easily conducted in DMSO solution at room temperature, with yields ranging from good to quantitative.

  邻碘氧苯甲酸（IBX）分别将伯醇和仲醇平滑氧化为醛和酮。1,2-二醇可转化为α-酮醇或α-二酮，而乙二醇CC键没有任何氧化裂解。IBX氧化很容易在室温下的DMSO溶液中进行，收率范围从良好到定量。
• Brominating and oxidizing agent and method of using same
  申请人：Interx Research Corporation

  公开号：US04009178A1

  公开（公告）日：1977-02-22

  There is provided a brominating and oxidizing agent of the formula: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 which may be the same or different, represents a member selected from the group consisting of a hydrogen atom, a C.sub.1 -C.sub.22 straight or branched alkyl group, a phenyl group, and a substituted phenyl group whose substituents are selected from the group consisting of a methoxy group, a nitro group, a cyano group, a halogen atom (Br, Cl, I), a C.sub.1 -C.sub.2 dialkylamino group, a C.sub.1 -C.sub.2 dialkylaminomethyl group, a C.sub.1 -C.sub.2 dialkylaminoethyl group, a C.sub.1 -C.sub.2 dialkylammoniummethyl group, a C.sub.1 -C.sub.2 dialkylammoniumethyl group, a C.sub.1 -C.sub.2 trialkylammoniummethyl group, a C.sub.1 -C.sub.2 trialkylammoniumethyl group, a COOR.sub.5 group, and a CON(R.sub.5).sub.2 group, wherein R.sub.5 represents a C.sub.1 -C.sub.8 straight or branched alkyl group. The compounds falling within formula (I) find wide application as brominating and oxidizing agents in a number of organic reactions in which the prior art compound, N-bromosuccinimide has been employed to date. In comparison to N-bromosuccinimide, the compounds of the instant invention are characterized as being extremely stable to degradation and less polar with respect to their N-Br bond than N-bromosuccinimide such that promotion of "radical" bromine release is achieved with minimal positive bromine release.

  提供一种溴化和氧化剂，其化学式为：##STR1## 其中R.sub.1、R.sub.2、R.sub.3和R.sub.4可以相同也可以不同，代表所选自群组的成员，包括氢原子、C.sub.1-C.sub.22直链或支链烷基、苯基和取代苯基，其取代基选自群组，包括甲氧基、硝基、氰基、卤原子（溴、氯、碘）、C.sub.1-C.sub.2二烷基氨基、C.sub.1-C.sub.2二烷基氨甲基、C.sub.1-C.sub.2二烷基氨乙基、C.sub.1-C.sub.2二烷基铵甲基、C.sub.1-C.sub.2二烷基铵乙基、C.sub.1-C.sub.2三烷基铵甲基、C.sub.1-C.sub.2三烷基铵乙基、COOR.sub.5基团和CON（R.sub.5）.sub.2基团，其中R.sub.5代表C.sub.1-C.sub.8直链或支链烷基。符合式（I）的化合物在许多有机反应中作为溴化和氧化剂广泛应用，其中迄今为止已经使用的先前技术化合物N-溴代琥珀酰亚胺。与N-溴代琥珀酰亚胺相比，本发明的化合物具有极高的稳定性和较低的极性，其N-Br键相对于N-溴代琥珀酰亚胺来说，促进“自由基”溴释放的效果更好，溴释放量极小。
• Methods for Determining the Oncogenic Condition of Cell, Uses Thereof, and Methods for Treating Cancer
  申请人：INSERM (INSTITUT NATIONAL DE LA SANTE ET DE LA RECHERCHE MEDICALE)

  公开号：US20170176446A1

  公开（公告）日：2017-06-22

  The invention relates to methods for detecting the oncogenic condition of cells, including step where the amount of the OCDO compound in said cells is measured, and to the uses thereof. The invention further relates to OCDO inhibitors for use in methods for treating cancer.

  这项发明涉及检测细胞的致癌状态的方法，包括测量所述细胞中OCDO化合物的数量的步骤，以及其用途。该发明还涉及用于治疗癌症方法中使用的OCDO抑制剂。
• NANOMATERIALS
  申请人：Guide Therapeutics, Inc.

  公开号：US20210169804A1

  公开（公告）日：2021-06-10

  Lipid nanoparticle compositions for delivery of nucleic acids are described. The lipid nanoparticle may contain a conformationally constrained ionizable lipid as part of the composition. These compositions may allow for delivery of cargo without the need for a targeting ligand.

  描述了用于传递核酸的脂质纳米粒子组合物。脂质纳米粒子可能包含作为组合物的一部分的构象受限的可离子化脂质。这些组合物可能允许传递货物而无需靶向配体。
• Tin(<scp>II</scp>) chloride dihydrate–a mild reagent for the transformation of 6-nitro-Δ⁵-steroids to 5α-hydroxy-6-ketosteroids
  作者：Gireesh M. Singhal、Nalin B. Das、Ram P. Sharma

  DOI：10.1039/c39900000498

  日期：——

  Reaction of excess hydrated tin(II) chloride with 6-nitro-Δ5-steroids (1a–g) and (5) in tetrahydrofuran furnishes 5α-hydroxy-6-ketosteroids (2a–g) and (6) respectively, in good yields.

  过量水合氯化亚锡与6-硝基-Δ5-甾体（1a-g）及（5）在四氢呋喃中的反应，分别以良好产率得到5α-羟基-6-酮甾体（2a-g）及（6）。