4-(tert-butyl(diphenyl)silanyloxy)butyryl chloride | 131216-52-9

• 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
• 英文名称: 4-(tert-butyl(diphenyl)silanyloxy)butyryl chloride
• 英文别名: 4-[Tert-butyl(diphenyl)silyl]oxybutanoyl chloride
• CAS: 131216-52-9
• 化学式: C₂₀H₂₅ClO₂Si
• 分子量: 360.956
• InChiKey: VICNPIRPTXTGII-UHFFFAOYSA-N

物化性质

• 沸点：
  411.2±37.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.11
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(tert-butyl(diphenyl)silanyloxy)butyryl chloride 在 锂硼氢 、 sodium hexamethyldisilazane 作用下， 生成 (R)-4-(tert-butyldiphenylsilyloxy)-2-methylbutan-1-ol
  参考文献：
  名称：

  A practical synthesis of (−)-kazusamycin A (revised)

  摘要：

  We describe herein a stereo-controlled and practical synthesis of three key building blocks, namely Segment AB', Segment D, and Segment E' needed for the total synthesis of (-)-kazusamycin A. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.07.029
• 作为产物：
  描述：

  4-((tert-butyldiphenylsilyl)oxy)butanoic acid 在 草酰氯 作用下， 以 甲苯 为溶剂， 生成 4-(tert-butyl(diphenyl)silanyloxy)butyryl chloride
  参考文献：
  名称：

  非对映选择性、路易斯酸介导的联烯酸衍生物和 1,3-环戊二烯的 Diels-Alder 反应

  摘要：

  在其末端碳原子上具有不同取代基的丙二烯显示出轴向手性，并且可以通过光化学去外消旋化方案以对映体纯形式获得。现在已经研究了联烯酸衍生物在什么条件下与 1,3-环戊二烯发生 Diels-Alder 反应以及产生哪些产物。环状衍生物（内酰胺、内酯）经历由路易斯酸 Eu(fod) 3催化的外向选择性反应，而无环衍生物高度优先地产生内向产物 (EtAlCl 2作为优选的路易斯酸）。环外双键形成，具有出色的非对映选择性，手性转移接近完美。将该方法应用于倍半萜类β-檀香醇( 1 )和10( E )-β-檀香酸( 13 )的合成。

  DOI：

  10.1039/d3ob00598d

文献信息

• Synthesis of (+)-Methyl Dihydropalustramate and of the Pyrido[1,2-a]azepine Core of Stemona Alkaloids
  作者：Thorsten Bach、Camilla Mayer、Alexandra Romek

  DOI：10.1055/s-0034-1380685

  日期：——

  Starting from a readily available, enantiomerically pure 2,6-disubstituted piperidine the synthesis of pyrido[1,2-a]azepines was accomplished. Key reactions for the ring closure were a photochemically induced acyl radical addition or a SmI2-promoted ketyl radical addition to an α,β-unsaturated ester. En route to the cyclization precursor an epoxidiation/ring opening sequence led to an undesired oxazolidinone

  从容易获得的对映体纯的 2,6-二取代哌啶开始，完成了吡啶并 [1,2-a] 氮杂环庚烷的合成。闭环的关键反应是光化学诱导的酰基自由基加成或 SmI2 促进的羰基自由基加成到 α,β-不饱和酯。在环化前体的途中，环氧化/开环序列导致不想要的恶唑烷酮，结果证明它对配置分配有用。该化合物成功转化为(+)-甲基二氢palustramate。
• A Visible Light Driven Nickel Carbonylation Catalyst: The Synthesis of Acid Chlorides from Alkyl Halides
  作者：Kristian El Chami、Yi Liu、Mohammed A. Belahouane、Yiyang Ma、Pierre‐Louis Lagueux‐Tremblay、Bruce A. Arndtsen

  DOI：10.1002/anie.202213297

  日期：2023.3

  A visible light driven nickel carbonylation catalyst has been develop. This offers a method for carbonylative coupling reactions with an earth abundant metal at ambient temperature for the conversion of alkyl halides into synthetically versatile acid chlorides. The acid chlorides can then be transformed into an array of challenging ester, thioester and amide products.

  已经开发出可见光驱动的镍羰基化催化剂。这提供了一种在环境温度下与地球上丰富的金属进行羰基化偶联反应的方法，用于将卤代烷转化为合成用途广泛的酰氯。然后可以将酰氯转化为一系列具有挑战性的酯、硫酯和酰胺产品。
• Total Synthesis of Allocyathin B₂, a Metabolite of Bird's Nest Fungi
  作者：Motoo Tori、Naoko Toyoda、Masakazu Sono

  DOI：10.1021/jo971514s

  日期：1998.1.1

  Allocyathin B-2 has been synthesized using aldol reactions for construction of rings A and B, introduction of the side chain for ring B, cyclization of the acetyl group into a lactone, and construction of the seven-membered diene aldehyde during the last step.
• Formal Total Syntheses of the β-Lactam Antibiotics Thienamycin and PS-5
  作者：Peter A. Jacobi、Shaun Murphree、Frederic Rupprecht、Wanjun Zheng

  DOI：10.1021/jo952092u

  日期：1996.1.1

  Chiral nonracemic acetylenic acids of general structure 11, prepared using the Schreiber modification of the Nicholas reaction, have been converted to beta-amino acid derivatives of type 12 by a two-step sequence involving Curtius rearrangement followed by oxidative cleavage of the acetylenic bond. Amino acid derivatives 12 are excellent precursors for beta-lactams of the carbapenem class, including the important antibiotics thienamycin (1) and PS-5 (4).
• Triply convergent, stereospecific alkene formation via Peterson olefination
  作者：Anthony G. M. Barrett、John A. Flygare

  DOI：10.1021/jo00002a028

  日期：1991.1

  alpha-Iodo silanes 8 were prepared from alpha-hydroxy silanes and after halogen/metal exchange and treatment with copper(I) bromide-dimethyl sulfide were coupled with acid chlorides to yield alpha-silyl ketones 2. Cram controlled addition with a variety of nucleophiles followed by treatment with acid or base led to either the (E)- or (Z)-alkene in good overall yields from the iodide (47-67%) and with excellent stereoselectivities ( > 95/ < 5 for disubstituted cases and 67/33 to 95/5 for trisubstituted). The procedure was used iteratively in the total synthesis of 4(E),8(Z)-tetradecadien-1-yl acetate (15) in > 95/ < 5 isomeric purity.