(3β)-3-(butyn-1-yloxy)cholest-5-ene | 1022911-44-9

• 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: (3β)-3-(butyn-1-yloxy)cholest-5-ene
• 英文别名: (3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)-3-(pent-4-yn-1-yloxy)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene；(3β)-3-(but-3-yn-1-yloxy)cholest-5-ene；3-butynyl cholesteryl ether
• CAS: 1022911-44-9
• 化学式: C₃₁H₅₀O
• 分子量: 438.737
• InChiKey: OOJQEZIBCAYHGG-BWVDWJPHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.44
• 重原子数：
  32.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (3β)-3-(butyn-1-yloxy)cholest-5-ene 在 chromium(VI) oxide 、 氯化亚砜 、 间氯过氧苯甲酸 作用下， 以 吡啶 、 氯仿 、 水 、 丁酮 为溶剂， 反应 22.75h， 生成 3β-butynyloxycholest-4-en-6-one
  参考文献：
  名称：

  6E-Hydroximinosteroid homodimerization by cross-metathesis processes

  摘要：

  A rapid and efficient synthesis of 6E-hydroximinosteroid homodimers is described. The two new compounds were linked at position 3 of the steroid nucleus via a ruthenium catalyzed cross -metathesis reaction. The cytotoxic activity of these compounds was evaluated in vitro on human lung carcinoma A549 (ATCC CCL-185), colon adenocarcinoma HCT-116 (ATCC CCL-247), human caucasian glioblastoma multiforme T98G (ECACC 92090213) and human pancreatic adenocarcinoma PSN1 (ECACC 94060601) tumour cells. Homodimer 10b presented selective activity against HCT-116, although they are not highly toxic when compared with the monomer counterparts. (c) 2007 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2007.03.014
• 作为产物：
  描述：

  5-氯戊炔 、 胆固醇 在 sodium hydride 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 0.17h， 以33%的产率得到(3β)-3-(butyn-1-yloxy)cholest-5-ene
  参考文献：
  名称：

  金催化末端炔烃氧化为乙二醛及其与 2-苯基咪唑并[1,2-a]吡啶的反应：一锅法合成 1,2-二酮

  摘要：

  一种新颖的一锅法，可方便有效地合成 (2-苯基咪唑并[1,2- a ]吡啶-3-基)烷烃-1,2-二酮 ( 3 )，产率 (32–88%) 2-苯基咪唑并[1,2- a ]吡啶( 1 )和末端炔烃( 2 )已被建立，具有广泛的底物范围。串联反应序列包含金催化末端炔烃的双氧化以生成乙二醛，将 2-苯基咪唑并[1,2- a ]吡啶亲核加成到乙二醛以生成 α-羟基酮，以及将 α-羟基酮氧化以提供最终产品3该方法涉及在空气气氛下。简单的操作、温和的反应条件和广泛可用的底物使这种策略更实惠。

  DOI：

  10.1039/d1ob01507a

文献信息

• Iron-Catalyzed Regiodivergent Alkyne Hydrosilylation
  作者：Meng-Yang Hu、Peng He、Tian-Zhang Qiao、Wei Sun、Wen-Tao Li、Jie Lian、Jin-Hong Li、Shou-Fei Zhu

  DOI：10.1021/jacs.0c09083

  日期：2020.9.30

  bearing 2,9-diaryl-1,10-phenanthroline ligands exhibit not only unprecedented catalytic activity but also unusual ligand-controlled divergent regioselectivity in hydrosilylation reactions of various alkynes. The hydrosilylation protocol described herein provides a highly efficient method for preparing useful di- and trisubstituted olefins on a relatively large scale under mild conditions, and its use

  尽管人们对铁催化方法的开发付出了巨大的努力，但迄今为止报道的催化剂很少表现出明显优于其他金属催化剂的优势，而且大多数铁催化的机理仍不清楚。在此，我们报告了带有 2,9-二芳基-1,10-菲咯啉配体的铁配合物不仅表现出前所未有的催化活性，而且在各种炔烃的氢化硅烷化反应中还表现出不寻常的配体控制的发散区域选择性。本文所述的氢化硅烷化方案提供了一种在温和条件下以相对大规模制备有用的二取代和三取代烯烃的高效方法，其使用显着提高了许多生物活性化合物的合成效率。
• Synthesis and transformations of metallacycles. 45. Cross-cyclomagnesiation of 1,2-dienes in the synthesis of 5Z,9Z-dienoic acids, efficient inhibitors of human topoisomerase I
  作者：V. A. D’yakonov、L. U. Dzhemileva、A. A. Makarov、A. R. Mulyukova、R. A. Tuktarova、I. I. Islamov、U. M. Dzhemilev

  DOI：10.1007/s11172-015-1128-7

  日期：2015.9

  An original method for the synthesis of natural and synthetic 5Z,9Z-dienoic acids with high selectivity (>98%) and ~50% yields was elaborated. The method is based on a new Cp2TiCl2catalyzed cross-cyclomagnesiation reaction of terminal aliphatic and O-containing 1,2-dienes using Grignard reagents. The synthesized acids exhibited in vitro high inhibiting activity against human topoisomerase I.

  详细阐述了一种以高选择性 (>98%) 和 ~50% 产率合成天然和合成 5Z,9Z-二烯酸的原始方法。该方法基于使用格氏试剂对末端脂肪族和含 O 的 1,2-二烯进行新的 Cp2TiCl2 催化交叉环镁化反应。合成的酸在体外对人拓扑异构酶 I 表现出高抑制活性。
• C-3β-Tethered Functional Cholesterol Conjugates by Nitrile Oxide Alkyne Cycloaddition (NOAC)
  作者：Virginie Algay、Justine O'Sullivan、Frances Heaney

  DOI：10.1002/ejoc.201301822

  日期：2014.4

  Covalent cholesterol conjugates have been prepared by isoxazole-generating [3+2] nitrile oxide alkyne cycloaddition (NOAC) chemistry. Steroidal building blocks functionalised with either an alkyne or a nitrile oxide precursor were evaluated. The reaction has been demonstrated for the tethering to cholesterol of groups capable of bioreporting, and for the formation of cholesterol–biomolecule conjugates

  共价胆固醇结合物已通过产生异恶唑的 [3+2] 腈氧化物炔环加成 (NOAC) 化学制备。评估了用炔烃或腈氧化物前体功能化的甾体结构单元。该反应已被证明可以将具有生物报告能力的基团束缚在胆固醇上，并形成胆固醇-生物分子偶联物。
• Catalytic cyclometallation in steroid chemistry III1Steroids 78 (12–13) (2013) 1298–1303 (http://dx.doi.org/10.1016/j.steroids.2013.09.007).1: Synthesis of steroidal derivatives of 5Z,9Z-dienoic acid and investigation of its human topoisomerase I inhibitory activity
  作者：Vladimir A. D’yakonov、Lilya U. Dzhemileva、Regina A. Tuktarova、Aleksey A. Makarov、Ilgiz I. Islamov、Alfiya R. Mulyukova、Usein M. Dzhemilev

  DOI：10.1016/j.steroids.2015.08.006

  日期：2015.10

  Two approaches to stereoselective synthesis of steroid 5Z,9Z-dienoic acids were developed, the first one being based on the cross-cyclomagnesiation of 2-(hepta-5,6-dien-1-yloxy)tetrahydro-2H-pyran and 1,2-diene cholesterol derivatives on treatment with EtMgBr catalyzed by Cp2TiCl2, while the other involving the synthesis of esters of hydroxy steroids with (5Z,9Z)-tetradeca-5,9-dienedioic acid, prepared in two steps using homo-cyclomagnesiation of 2-(hepta-5,6-dien-1-yloxy)tetrahydro-2H-pyran as the key step. High inhibitory activity of the synthesized acids against human topoisomerase I (hTop1) was found. (C) 2015 Published by Elsevier Inc.