3β,17β-diacetoxy-5α-androstane | 5424-40-8

• 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,17β-diacetoxy-5α-androstane
• 英文别名: 5α-androstane-3β,17β-diol diacetate；5α-androstane-3β,17β-diyl diacetate；5α-androstan-3β,17β-diyl diacetate；3β,17β-Diacetoxy-5α-androstan；(10S)-3c.17c-Diacetoxy-10r.13c-dimethyl-(5tH.8cH.9tH.14tH)-hexadecahydro-1H-cyclopenta[a]phenanthren；5α-Androstandiyl-(3β.17β)-diacetat；3beta,17beta-Diacetoxy-5alpha-androstane；[(3S,5S,8R,9S,10S,13S,14S,17S)-17-acetyloxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
• CAS: 5424-40-8
• 化学式: C₂₃H₃₆O₄
• 分子量: 376.536
• InChiKey: BQIBBYLXJDSLIR-FTQGCKHGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.91
• 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：

  3β,17β-diacetoxy-5α-androstane 在 chromium(VI) oxide 、 甲醇 、 氢氧化钾 、 溶剂黄146 作用下， 生成 (10,13-二甲基-3-氧代-1,2,4,5,6,7,8,9,11,12,14,15,16,17-十四氢环戊烯并[a]菲-17-基)乙酸酯
  参考文献：
  名称：

  Butenandt; Dannenberg, Chemische Berichte, 1936, vol. 69, p. 1158,1161

  摘要：

  DOI：
• 作为产物：
  描述：

  1-雄烯二酮 在 吡啶 、 sodium 作用下， 生成 3β,17β-diacetoxy-5α-androstane
  参考文献：
  名称：

  Butenandt; Dannenberg, Chemische Berichte, 1940, vol. 73, p. 206,208

  摘要：

  DOI：

文献信息

• Microwave induced selective enolization of steroidal ketones and efficient acetylation of sterols in semisolid state
  作者：Padma Marwah、Ashok Marwah、Henry A. Lardy

  DOI：10.1016/s0040-4020(03)00207-2

  日期：2003.3

  Under microwave irradiation steroidal enones, more specifically, position three carbonyls were efficiently and selectively converted to the corresponding enol acetates in the presence of additional enolizable carbonyl functions at other positions, using acetic anhydride and a catalytic amount of toluene-p-sulfonic acid. Acetylation of hydroxyl groups of the sterols, including those at the hindered

  在微波辐射下，更具体地，使用乙酸酐和催化量的甲苯-对磺酸，在其他位置存在另外的可烯丙基的羰基官能团的情况下，在其他位置上，将三个位置的羰基化合物有效且选择性地转化为相应的烯醇乙酸酯。固醇的羟基的乙酰化，包括在受阻位置的羟基，几乎是定量的。严格的无水条件不是乙酰化的前提条件，反应系统很容易耐受高达10％（v / v）的水分。
• Expedited Baeyer–Villiger oxidation of steroidal ketones by microwave irradiation
  作者：Juri Moni Borah、Pritish Chowdhury

  DOI：10.1016/j.steroids.2011.06.014

  日期：2011.11

  compounds. Considering the remarkable application of Baeyer-Villiger (BV) reaction in the synthesis of natural products and steroid-peptide conjugates, we report here some of our findings of BV oxidation of carbonyl compounds with special reference to steroidal ketones under MW irradiation justifying its accelerating effect.

  微波（MW）辅助反应目前在有机化合物的合成中具有相当重要的意义。考虑到Baeyer-Villiger（BV）反应在天然产物和类固醇-肽共轭物的合成中的显着应用，我们在此报告了MW辐射下羰基化合物BV氧化的一些发现，特别是甾体酮，证明了其加速作用。
• Enzymatic transesterification of steroid esters in organic solvents
  作者：Vincent C.O. Njar、Eliahu Caspi

  DOI：10.1016/s0040-4039(00)96910-7

  日期：——

  A mild procedure for the conversion of steroid esters into the corresponding alcohols via lipase-catalyzed transesterification reaction in organic solvents is described. Aspects of stereoselectivity and regioselectivity of the reaction are noted.

  描述了一种在有机溶剂中通过脂肪酶催化的酯交换反应将甾族酯转化为相应醇的温和方法。记录了反应的立体选择性和区域选择性的方面。
• Qualitative Analysis of the Clinician Interview-Based Impression of Change (Plus): Methodological Issues and Implications for Clinical Research
  作者：Christine Joffres、Janice Graham、Kenneth Rockwood

  DOI：10.1017/s1041610200006505

  日期：2000.9

  The Clinician Interview-Based Impression of Change, plus carer interview (CIBIC-Plus), is widely used in antidementia drug trials. It comprises Likert scales for disease severity and changes, and written accounts summarizing semistructured interviews evaluating behavior, cognition, and function. Studies using the CIBIC-Plus have focused on the numeric scores to the exclusion of the textual data. Our study explored both sets of data to evaluate whether the CIBIC-Plus written data supported (a) the clinicians' global evaluation of patients' changes during treatment, and (b) the emergence of consistent treatment effects. The global (numeric) scales of change were inconsistently supported by the textual data provided in the CIBIC-Plus. No consistent treatment effects were noted. Methodological problems presently limit the retrospective use of the CIBIC-Plus textual data. Improved standardization of note-taking in the CIBIC-Plus textual data may allow for a better understanding of the typical profiles and clinical importance of changes seen in the course of dementia treatment.

  基于临床医生访谈的变化印象加照护者访谈（CIBIC-Plus）被广泛用于抗痴呆药物试验。它包括疾病严重程度和变化的李克特量表，以及对行为、认知和功能进行评估的半结构式访谈的书面总结。使用 CIBIC-Plus 的研究主要集中在数字分数上，而忽略了文字数据。我们的研究探讨了这两组数据，以评估 CIBIC-Plus 的书面数据是否支持（a）临床医生对患者在治疗过程中的变化的总体评价，以及（b）一致的治疗效果的出现。CIBIC-Plus提供的文字数据对总体（数字）变化量表的支持并不一致。没有发现一致的治疗效果。目前，方法上的问题限制了 CIBIC-Plus 文本数据的回顾性使用。提高CIBIC-Plus文本数据记录的标准化程度，可以更好地了解痴呆症治疗过程中出现的变化的典型特征和临床重要性。
• Lipase-Catalysed Regioselective Deacetylation of androstane derivatives
  作者：Alicia Baldessari、Andrea C. Bruttomesso、Eduardo G. Gros

  DOI：10.1002/hlca.19960790408

  日期：1996.6.26

  series of acetoxy derivatives of androstane was deacetylated in organic solvents by several lipases. The most satisfactory results were obtained with lipase from Candida cylindracea (CCL) and Candida antarctica (CAL). In some derivatives, CCL and CAL showed an overwhelming regioselectivity towards the removal of the 3β- or the 17β-acetyl group (see Table 2). Three new steroid derivatives were obtained

  在多种有机溶剂中，几种脂肪酶使雄烷烷酮的一系列乙酰氧基衍生物脱乙酰化。用来自假丝酵母（CCL）和南极假丝酵母（CAL）的脂肪酶获得了最满意的结果。在某些衍生物中，CCL和CAL对除去3β-或17β-乙酰基表现出压倒性的区域选择性（参见表2）。通过这种方法获得了三种新的类固醇衍生物。给出了这些酶的行为的假设原理。