(E)-5-trimethylsilyl-2-(2-trimethylsilylethynyl)pent-2-en-4-yn-1-ol | 131761-09-6

• 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: (E)-5-trimethylsilyl-2-(2-trimethylsilylethynyl)pent-2-en-4-yn-1-ol
• CAS: 131761-09-6
• 化学式: C₁₃H₂₂OSi₂
• 分子量: 250.488
• InChiKey: VVTNDKWPFMTDKU-MDWZMJQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.67
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.54
• 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：

  (E)-5-trimethylsilyl-2-(2-trimethylsilylethynyl)pent-2-en-4-yn-1-ol 在 水 、 sodium trimethoxyborohydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 以60%的产率得到(E)-2-Ethynyl-5-trimethylsilanyl-pent-2-en-4-yn-1-ol
  参考文献：
  名称：

  Enantioselective synthesis of the epoxy diyne core of neocarzinostatin chromophore

  摘要：

  DOI：

  10.1021/ja00002a059
• 作为产物：
  描述：

  ethyl (Z)-2-bromo-5-trimethylsilylpent-2-en-4-ynoate 在 copper(l) iodide 、 二异丁基氢化铝 、 钯 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 16.17h， 生成 (E)-5-trimethylsilyl-2-(2-trimethylsilylethynyl)pent-2-en-4-yn-1-ol
  参考文献：
  名称：

  Toward the Construction of Enediyne Prodrug Systems Related to the Ring Expanded Artifact Produced Upon Isolation of Maduropeptin Chromophore

  摘要：

  As part of a modular approach to synthesize maduropeptin analogues of general formula 3, the diacetylene substituted dihydro-1,2-oxazine synthon 13 was constructed via a hetero Diels-Alder reaction between diene 10 and the nitrosodienophile 12. Reductive cleavage of the N-O bond in 13, and acylation of the derived amine 16 gave the stable amide 17. (C) 1997 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(97)10459-2

文献信息

• Magnesium mediated carbometallation of propargyl alcohols: direct routes to dihydroxydienes and enediyne alcohols
  作者：Pat Forgione、Alex G Fallis

  DOI：10.1016/s0040-4039(99)01994-2

  日期：2000.1

  The addition of vinyl and alkynyl Grignard reagents to propargyl alcohols for the direct synthesis of dihydroxydienes and enediyne alcohols from a one pot reaction is described. These products arise from the putative magnesium chelate intermediate 2 upon reaction with the appropriate electrophile. (C) 1999 Elsevier Science Ltd. All rights reserved.
• MYERS, ANDREW G.;HARRINGTON, PHILIP M.;KUO, ELAINE Y., J. AMER. CHEM. SOC., 113,(1991) N, C. 694-695
  作者：MYERS, ANDREW G.、HARRINGTON, PHILIP M.、KUO, ELAINE Y.

  DOI：——

  日期：——
• Toward the Construction of Enediyne Prodrug Systems Related to the Ring Expanded Artifact Produced Upon Isolation of Maduropeptin Chromophore
  作者：Cécile Roger、David S Grierson

  DOI：10.1016/s0040-4039(97)10459-2

  日期：1998.1

  As part of a modular approach to synthesize maduropeptin analogues of general formula 3, the diacetylene substituted dihydro-1,2-oxazine synthon 13 was constructed via a hetero Diels-Alder reaction between diene 10 and the nitrosodienophile 12. Reductive cleavage of the N-O bond in 13, and acylation of the derived amine 16 gave the stable amide 17. (C) 1997 Published by Elsevier Science Ltd. All rights reserved.
• Enantioselective synthesis of the epoxy diyne core of neocarzinostatin chromophore
  作者：Andrew G. Myers、Philip M. Harrington、Elaine Y. Kuo

  DOI：10.1021/ja00002a059

  日期：1991.1