1-(trimethylsilyl)-1-decyn-3-ol | 140149-76-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(trimethylsilyl)-1-decyn-3-ol
• 英文别名: 1-(trimethylsilyl)dec-1-yn-3-ol；1-trimethylsilyl-l-decyn-3-ol；1-Decyn-3-ol, 1-(trimethylsilyl)-；1-trimethylsilyldec-1-yn-3-ol
• CAS: 140149-76-4
• 化学式: C₁₃H₂₆OSi
• 分子量: 226.434
• InChiKey: KGFXSPBJDFBTEO-UHFFFAOYSA-N

物化性质

• 沸点：
  289.5±13.0 °C(Predicted)
• 密度：
  0.870±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.59
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(trimethylsilyl)-1-decyn-3-ol 在 Jones reagent 、 potassium carbonate 、 三氟乙酸 、 lithium chloride 作用下， 以 甲醇 、 异丙醇 、 丙酮 为溶剂， 反应 7.0h， 生成 (E)-1-chlorodec-1-en-3-one
  参考文献：
  名称：

  Selective Activation/Coupling of Polyhalogenated Nucleophiles in Ni/Cr-Mediated Reactions: Synthesis of C1–C19 Building Block of Halichondrin Bs

  摘要：

  The C1-C19 building block 46 of halichondrin Bs was synthesized via a selective activation/coupling of beta-bromoenone 34 with aldehyde 35 in a Ni/Cr-mediated reaction. The first phase of study was a method development to effect a coupling of a naked vinylogous anion with an aldehyde. The study with the coupling of 9 + 10 -> 11 revealed: (1) beta-bromoenone 9b is a better nucleophile than the corresponding beta-iodo- and beta-chloroenones 9a,c; (2) (Me)(2)Phen(OMe)(2)center dot NiCl2 13b is a better Ni-catalyst than (Me)(2)Phen(H)(2)center dot NiCl2 13a; and (3) a low Ni-catalyst loading, for example, 0.05-0.1 mol % Ni-catalyst against 10 mol % Cr-catalyst, is crucial for an effective coupling. The second phase of study was a method development to realize a selective activation/coupling of polyhalogenated nucleophiles such as 34. The competition experiment of 10 + 9b over 10 + 31a-c revealed: (1) (Me)(2)Phen(OMe)(2)center dot NiCl2 13b is more effective than (Me)(2)Phen(H)(2)center dot NiCl2 13a for the required selective activation/coupling; (2) a low Ni-catalyst loading, for example, 0.05-0.1 mol % Ni-catalyst against 10 mol % Cr-catalyst, is crucial for discriminating beta-bromoenone 9b from the three types of vinyl iodides 31a-c. The third phase of study was an application of the developed method to execute the proposed coupling of 34 + 35 -> 36. For this application, a polyether-type Ni-catalyst 37c, readily soluble in the reaction medium, was introduced to achieve the selective activation/coupling with higher efficiency. With use of ion-exchange resin-based device, the coupling product 36 was transformed to the C1-C19 building block 46 of halichondrin Bs without purification/separation of the intermediates.

  DOI：

  10.1021/jacs.5b03498
• 作为产物：
  描述：

  正辛醛 、 三甲基乙炔基硅 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.0h， 生成 1-(trimethylsilyl)-1-decyn-3-ol
  参考文献：
  名称：

  金催化丙醇与芳香族化合物的分子间反应合成丙二烯

  摘要：

  通过金催化的炔丙醇和芳族化合物的分子间反应，可以中等至高收率有效地合成官能化的烯。用户友好的过程可以在温和的反应条件下用容易获得的原料进行。

  DOI：

  10.1021/jo300147u

文献信息

• Gold-Catalyzed One-Step Practical Synthesis of Oxetan-3-ones from Readily Available Propargylic Alcohols
  作者：Longwu Ye、Weimin He、Liming Zhang

  DOI：10.1021/ja1033952

  日期：2010.6.30

  A general solution for the synthesis of various oxetan-3-ones is developed. This reaction uses readily available propargylic alcohols as substrates and proceeds without the exclusion of moisture or air ("open flask"). Notably, oxetan-3-one, a highly valuable substrate for drug discovery, can be prepared in one step from propargyl alcohol in a fairly good yield. The facile formation of the strained

  开发了合成各种 oxetan-3-ones 的通用解决方案。该反应使用容易获得的炔丙醇作为底物并且在不排除水分或空气的情况下进行（“开放烧瓶”）。值得注意的是，oxetan-3-one 是一种非常有价值的药物发现底物，可以在一个步骤中从炔丙醇以相当好的收率制备。应变氧杂环丁烷环的轻松形成为α-氧代金卡宾的中间体提供了强有力的支持。这种通过分子间炔烃氧化安全有效地生成金卡宾为 α-氧代金属卡宾化学提供了一种潜在的通用方法，而无需使用危险的重氮酮。
• Asymmetric Total Synthesis of (−)-Awajanomycin
  作者：Rui Fu、Jie Chen、Lu-Chuan Guo、Jian-Liang Ye、Yuan-Ping Ruan、Pei-Qiang Huang

  DOI：10.1021/ol902180t

  日期：2009.11.19

  The first asymmetric total synthesis of the unnatural enantiomer of cytotoxic awajanomycin (1) is reported. The synthetic approach features first a convergent strategy using the cross-olefin metathesis reaction to link the lipid side chain 2 and the piperidinone core structure 3. The second feature of the synthesis resides on the construction of segment 3 from the building block 5 via a three-component

  报道了细胞毒性阿维霉素的非天然对映异构体的首次不对称全合成（1）。合成方法的特征首先是使用交叉烯烃复分解反应连接脂质侧链2和哌啶酮核心结构3的收敛策略。合成的第二个特征在于通过混合酰亚胺12上的三组分串联反应，由结构单元5构建片段3。通过这项工作，确定了C-11的立体化学和阿瓦那霉素的绝对构型为3 R，5 R，6 S，8 S，11 S。
• New organoboron reagents for the preparation unsubstituted propargylic
  申请人：Merrell Dow Pharmaceuticals Inc.

  公开号：US05110966A1

  公开（公告）日：1992-05-05

  The novel organoboron reagent of the present invention is useful in the preparation of unsubstituted propargylic alcohols. This compound reacts with aldehydes and ketones cleanly to afford propargylic alcohols in excellent yields. Unsubstituted propargylic alcohols are important synthetic intermediates in the synthesis of a number of natural products. In addition, the novel organoboron reagent of the present invention also demonstrates diastereomeric selectivity when reacted with enatiomerically pure aldehydes.

  本发明的新型有机硼试剂在制备未取代的丙炔醇中非常有用。该化合物与醛和酮反应干净，可以得到产率极高的丙炔醇。未取代的丙炔醇是合成许多天然产物的重要中间体。此外，本发明的新型有机硼试剂在与对映纯醛反应时还表现出对映选择性。
• Organoboron reagents for the preparation of unsubstituted propargylic
  申请人：Merrell Dow Pharmaceuticals Inc.

  公开号：US05157167A1

  公开（公告）日：1992-10-20

  The novel organoboron reagent of the present invention is useful in the preparation of unsubstituted propargylic alcohols. This compound reacts with aldehydes and ketones cleanly to afford propargylic alcohols in excellent yields Unsubstituted propargylic alcohols are important synthetic intermediates in the synthesis of a number of natural products. In addition, the novel organoboron reagent of the present invention also demonstrates diastereomeric selectivity when reacted with enatiomerically pure aldehydes.

  本发明的新型有机硼试剂在制备未取代丙炔醇方面非常有用。该化合物与醛和酮反应干净，可以得到产率极高的丙炔醇。未取代的丙炔醇是合成许多天然产物的重要中间体。此外，本发明的新型有机硼试剂在与对映纯醛反应时也表现出对映异构体选择性。
• Two‐Dimensional Detergent Expansion Strategy for Membrane Protein Studies
  作者：Fei Zhao、Zhihao Zhu、Linshan Xie、Feng Luo、Huixia Wang、Yanli Qiu、Weiling Luo、Fang Zhou、Dongxiang Xue、Zhihui Zhang、Tian Hua、Dong Wu、Zhi‐Jie Liu、Zhiping Le、Houchao Tao

  DOI：10.1002/chem.202201388

  日期：2022.8.4

  Detergents are the most frequently applied reagents in membrane protein (MP) studies. The limited diversity of one-head-one-tailed traditional detergents, however, is far from sufficient for structurally distinct MPs. Expansion of detergent repertoire has a continuous momentum. In line with the speculation that detergent pre-assembly exerts superiority, herein we report for the first time cross-conjugation

  去污剂是膜蛋白 (MP) 研究中最常用的试剂。然而，一头一尾传统洗涤剂的有限多样性对于结构不同的 MP 来说还远远不够。洗涤剂品种的扩张势头不断。与去污剂预组装发挥优势的推测一致，本文首次报道了两个系列单体去污剂的交叉共轭，用于构建二聚去污剂的二维库。最佳去污剂在个体 MP 的系统评估中具有独特的偏好。此外，前所未有的混合去污剂 14M8G 和 14M9G 分别实现了转运蛋白 MsbA 的高质量 EM 研究和 G 蛋白偶联受体 A2A AR 的 NMR 研究。鉴于交叉偶联化学物质的丰富性，