1-戊炔-3-酮,4-甲基-1-[三(1-甲基乙基)甲硅烷基]- | 183852-51-9

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 中文名称: 1-戊炔-3-酮,4-甲基-1-[三(1-甲基乙基)甲硅烷基]-
• 英文名称: 4-methyl-1-(triisopropylsilyl)pent-1-yn-3-one
• 英文别名: 4-methyl-1-tri(propan-2-yl)silylpent-1-yn-3-one
• CAS: 183852-51-9
• 化学式: C₁₅H₂₈OSi
• 分子量: 252.472
• InChiKey: NVHMRUAHDYWCER-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.43
• 重原子数：
  17.0
• 可旋转键数：
  4.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  1-戊炔-3-酮,4-甲基-1-[三(1-甲基乙基)甲硅烷基]- 在 4-二甲氨基吡啶 、 (S)-B-n-Bu-oxazaborolidine 、 三乙胺 、 儿萘酚硼烷 作用下， 以 二氯甲烷 为溶剂， 生成 Benzoic acid (R)-1-isopropyl-3-triisopropylsilanyl-prop-2-ynyl ester
  参考文献：
  名称：

  An Efficient Catalytic Stereoselective Route to a Key Intermediate for the Synthesis of the Long-Lived PGI2 Analog ZK 96480 (CicaprostTM)

  摘要：

  An expeditious and stereoselective synthesis of a key chiral intermediate (2) for the synthesis of the therapeutically useful PGI(2) analog Cicaprost(TM) is described. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01803-0
• 作为产物：
  描述：

  三异丙基氯硅烷 在 正丁基锂 、 三氯化铝 作用下， 以 二氯甲烷 为溶剂， 生成 1-戊炔-3-酮,4-甲基-1-[三(1-甲基乙基)甲硅烷基]-
  参考文献：
  名称：

  Direct Catalytic Enantioselective Reduction of Achiral α,β-Ynones. Strong Remote Steric Effects Across the C−C Triple Bond

  摘要：

  DOI：

  10.1021/ja962849e

文献信息

• Highly Regioselective and <i>E</i>/<i>Z</i>-Selective Hydroalkylation of Ynone, Ynoate, and Ynamide via Photoredox Mediated Ni/Ir Dual Catalysis
  作者：Su Yong Go、Geun Seok Lee、Soon Hyeok Hong

  DOI：10.1021/acs.orglett.8b02017

  日期：2018.8.3

  Exclusively α- and highly E/Z-selective hydroalkylation of ynone, ynoate, and ynamide was achieved via photoredox mediated Ni/Ir dual catalysis with high atom and step economy, producing trisubstituted enones, which are versatile synthetic building blocks. The developed reaction selectively delivered the α/Z isomer, which is complementary to the previously reported β-alkylation processes. The trisubstituted

  通过光氧化还原介导的Ni / Ir双重催化，高原子和步长经济性，实现了对酮，炔酸酯和炔酰胺的α-和高度E / Z选择性加氢烷基化反应，产生了三取代的烯酮，这是通用的合成原料。发达的反应选择性地递送了α/ Z异构体，这与先前报道的β-烷基化过程是互补的。三取代的烯酮可以通过后官能化转化为更有价值的化合物。
• Iterative Synthesis and Characterization of Cross-Conjugated Iso-Polydiacetylenes
  作者：Yuming Zhao、Katie Campbell、Rik R. Tykwinski

  DOI：10.1021/jo015810n

  日期：2002.1.1

  An iterative synthesis of cross-conjugated iso-polydiacetylenes (iso-PDAs) is reported based on three fundamental building blocks: vinyl triflates 8, 9, and 25. An efficient sequence of palladium-catalyzed cross-coupling reactions of vinyl triflates and terminal alkynes has been employed to extend the chain length of these oligomers. The longest member of the series, nonamer 19, spans 3.4 nm from Si

  据报道，基于三个基本组成部分：乙烯基三氟甲磺酸8、9和25，对交叉共轭的异聚二乙炔（iso-PDA）进行了迭代合成。乙烯基三氟甲磺酸与末端炔烃的钯催化交叉偶联反应的有效顺序已经使用“链延长”来延长这些低聚物的链长。该系列中最长的成员，九聚体19，从Si到Si原子跨度为3.4 nm。已评估了共轭低聚物的稳定性和溶解度，这是侧基取代的函数。通过对单体12和三聚体14进行X射线晶体学分析，可以评估固态结构的性能。单分散低聚物的电子特性已通过紫外可见光谱法在溶液和薄膜中进行了全面分析。
• Highly Enantiospecific Platinum-Catalyzed Cycloisomerizations: Synthesis of Enantioenriched Oxabicycloheptene Derivatives
  作者：Eric T. Newcomb、Eric M. Ferreira

  DOI：10.1021/ol400625f

  日期：2013.4.5

  Enantiospecific cycloisomerizations of 1,6-enynes to form oxabicyclo[4.1.0]heptene derivatives are described. Enantiospecificity is consistently high regardless of alkene or alkyne substitution, providing a general approach to greatly enantioenriched cyclopropanes. Additionally, a model for stereochemical transfer is proposed.
• A General Synthesis of Ynones from Aldehydes via Oxidative C–C bond Cleavage under Aerobic Conditions
  作者：Zhaofeng Wang、Li Li、Yong Huang

  DOI：10.1021/ja506352b

  日期：2014.9.3

  We describe a direct synthesis of various ynones from readily available aldehydes and hypervalent alkynyl iodides. In this method, a gold catalyst and a secondary amine work synergistically to produce the trisubstituted allenyl aldehyde, which can be converted to the desired ynone through an in situ C-C bond oxidative cleavage using molecular oxygen.