3β-chlorocholest-5-en-7-one | 55105-71-0

• 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-chlorocholest-5-en-7-one
• 英文别名: 7-ketocholesteryl chloride；3beta-Chlorocholest-5-en-7-one；(3S,8S,9S,10R,13R,14S,17R)-3-chloro-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,3,4,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-7-one
• CAS: 55105-71-0
• 化学式: C₂₇H₄₃ClO
• 分子量: 419.091
• InChiKey: VDRMMBBYKKUFPP-ABXCMAEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3β-chlorocholest-5-en-7-one 在 盐酸胍 、 sodium tetrahydroborate 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 以84%的产率得到3β-chlorocholest-5-en-7-ol
  参考文献：
  名称：

  Selective Reduction of a,b-Unsaturated Steroidal Carbonyl Compounds by NaBH4 in Presence of Guanidine Hydrochloride in Dioxane

  摘要：

  描述了一种在二氧六烷中，以氢化铵和氯化胍为催化剂，选择性氢化α, β-不饱和类固醇碳基化合物的反应，产率从良好到优异。

  DOI：

  10.14233/ajchem.2014.16363
• 作为产物：
  描述：

  cholesteryl chloride 在 tBuOCrO3H 作用下， 生成 3β-chlorocholest-5-en-7-one
  参考文献：
  名称：

  Synthesis and in vitro antibacterial activity of new steroidal thiosemicarbazone derivatives

  摘要：

  We investigated the antibacterial activity of some new steroidal thiosemicarbazone derivatives, prepared from the reaction of cholest-5-en-7-one with thiosemicarbazides, in ethanol in the presence of a few drops of HCl at 80 degrees C in high yield. All the compounds have been characterized by means of elemental analyses, IR, H-1 NMR and mass spectroscopic data, to find an effective antibacterial agent. The antibacterial activity was first tested in vitro by the disk diffusion assay against two Gram-positive and two Gram-negative bacteria, and then the minimum inhibitory concentration (MIC) of compounds was determined. The results showed that the steroidal thiosemicarbazones derivatives inhibit growth of both types of the bacteria (Gram-positive and Gram-negative). The acetoxy and chloro derivatives of cyclopentyl and cyclohexyl amine thiosemicarbazones were found to have more antibacterial activity than the other derivatives. (C) 2008 Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2007.12.004

文献信息

• Metal-Free Allylic Oxidation of Steroids Using TBAI/TBHP Organocatalytic Protocol
  作者：Ying-Pong Lam、Ying-Yeung Yeung

  DOI：10.1002/asia.201800256

  日期：2018.9.4

  A mild, efficient and organocatalytic allylic oxidation of steroids using a TBAI/TBHP protocol has been developed. A range of bioactive Δ5‐en‐7‐ones can be easily prepared from the corresponding Δ5‐steroids. The methodology features several advantages, including readily available starting materials, environmentally benign oxidant, high functional group compatibility, and metal‐free catalysis.

  已经开发了使用TBAI / TBHP方案进行的类固醇的温和，有效和有机催化的烯丙基氧化。生物活性Δ的范围5 -烯-7-酮可以由相应的Δ容易地制备5 -steroids。该方法具有许多优点，包括容易获得的起始原料，对环境无害的氧化剂，高官能团相容性和无金属催化作用。
• Sensitized Aliphatic Fluorination Directed by Terpenoidal Enones: A “Visible Light” Approach
  作者：Desta Doro Bume、Stefan Andrew Harry、Cody Ross Pitts、Thomas Lectka

  DOI：10.1021/acs.joc.7b02807

  日期：2018.2.2

  challenges of selective sp3 C–H fluorination on complex molecules, we report a sensitized aliphatic fluorination directed by terpenoidal enones using catalytic benzil and visible light (white LEDs). This sensitized approach is mild, simple to set up, and an economical alternative to our previous protocol based on direct excitation using UV light in a specialized apparatus. Additionally, the amenability

  在我们为应对复杂分子上选择性sp 3 C–H氟化反应所做出的不断努力中，我们报道了由萜烯烯酮利用催化苯甲酸酯和可见光（白色LED）指导的敏化脂肪族氟化反应。这种敏化方法温和，易于设置，并且是基于以前在专用设备中使用紫外线直接激发的协议的经济替代方案。此外，该协议对光化学流动条件的适应性以及电子转移过程的初步证据也得到了强调。
• Synthesis, structure elucidation and antibacterial evaluation of new steroidal -5-en-7-thiazoloquinoxaline derivatives
  作者：Salman Ahmad Khan、Kishwar Saleem、Zaheer Khan

  DOI：10.1016/j.ejmech.2007.09.022

  日期：2008.10

  cholest-5-en-7-one-thiosemicarbazone with 2,3-dichloroquinoxaline at 80 degrees C in high yield. The thiosemicarbazone derivatives were obtained by the condensation of the thiosemicarbazide with steroidal ketones. All the compounds have been characterized by means of elemental analyses, IR, 1H NMR and mass spectroscopic data. The in vitro antibacterial activity was evaluated by disk diffusion method

  通过胆甾-5-烯-7-一硫代半碳酰胺与2,3-的反应合成了一些杂环体系，即胆甾-5-烯-7-噻唑并[4,5-b]喹喔啉-2-基-]在80摄氏度下高产二氯喹喔啉。硫代氨基脲衍生物是通过使硫代氨基脲与甾族酮缩合而获得的。所有化合物均已通过元素分析，IR，1H NMR和质谱数据进行了表征。通过圆盘扩散法评价体外抗菌活性，然后测定化合物对大肠杆菌培养物的最小抑菌浓度（MIC）。将结果与标准药物氯霉素进行比较。结果表明，与氯霉素相比，化合物7和8是更好的抗菌剂。
• Studies Toward the Thermally Induced One-Step Intermolecular Synthesis of Azacyclic Steroidal Ketones
  作者：M. Gulfam Alam、Tabassum Siddiqui

  DOI：10.1080/00397910802640020

  日期：2009.5.22

  Abstract We describe the route for the preparation of azacyclic steroidal compounds 2 and 4a–c through double Mannich reaction from cholest-5-en-3-one 1, cholest-5-en-7-one 3a, and 3β-substituted cholest-5-en-7-ones 3b, c as starting material.

  摘要 我们描述了通过 cholest-5-en-3-one 1、cholest-5-en-7-one 3a 和 3β-取代的 cholest- 的双曼尼希反应制备氮杂环甾体化合物 2 和 4a-c 的路线。 5-en-7-ones 3b，c 作为起始材料。
• Synthesis of steroidal dimers: Selective amine catalysed steroidal dimerization
  作者：SHAMSUZZAMAN、MOHD GULFAM ALAM、TABASSUM SIDDIQUI

  DOI：10.1007/s12039-011-0099-y

  日期：2011.7

  Some new dimeric steroids namely cholest-5-en-3-spiro-[6′ α,5′-oxa]-5′ α-cholest-3′-one (2), cholest-5-en-7-spiro-[4′ α,5′-oxa]-5′ α-cholest-7′-one (4a) and 3β-substitutedcholest-5-en-7-spiro-[4′ α,5′-oxa]-3′ β-substituted-5′ α-cholestan-7′-ones (4b, c) are synthesized starting from cholest-5-en-3-one (1), cholest-5-en-7-one (3a) and 3β-substituted-cholest-5-en-7-ones (3b, c) respectively by using

  一些新的二聚类固醇即胆甾-5-烯-3-螺- [6 ' α，5 '氧杂] -5 ' α -cholest-3 ' -酮（2），胆甾-5-烯-7-螺[4 ' α，5 '氧杂] -5 ' α -cholest-7 ' -酮（图4a）和3 β -substitutedcholest -5-烯-7-螺- [4 ' α，5 '氧杂] -3- ' β取代-5 ' α -胆甾7 ' -酮（图4b，C）被合成开始从胆甾-5-烯-3-酮（1），通过使用DMAP和二甲苯分别将cholest-5-en-7-ones（3a）和3个β-取代的cholest-5-en-7-ones（3b，c）。所有合成的化合物均通过IR，MS和1 H，13 C NMR光谱和元素分析进行表征。 甾体二聚体（2，图4A-C ）已经被甾酮（反应合成1，图3A-C ），在二甲苯DMAP。合成的化合物通过IR，MS和1 H，13 C NMR光谱技术和元素分析进行表征。