(Z)-1-trimethylsilylundec-5-en-1-yn-3-one | 127705-33-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (Z)-1-trimethylsilylundec-5-en-1-yn-3-one
• CAS: 127705-33-3
• 化学式: C₁₄H₂₄OSi
• 分子量: 236.429
• InChiKey: UKWONPDPEXRUSL-KTKRTIGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.96
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (Z)-1-trimethylsilylundec-5-en-1-yn-3-one 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 (R)-BINAL-H 、 四丁基氟化铵 、 红铝 作用下， 生成 U 75302
  参考文献：
  名称：

  Asymmetric synthesis of the diastereoisomers of the leukotriene B4 antagonist, U-75302

  摘要：

  DOI：

  10.1016/s0040-4039(01)93452-5
• 作为产物：
  描述：

  顺-3-壬烯-1-醇 在 正丁基锂 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 (Z)-1-trimethylsilylundec-5-en-1-yn-3-one
  参考文献：
  名称：

  Enantioselective synthesis of cyclopropyl δ-lactonealdehydes and dodecyl-5-ene-1-yne-3-ol: advanced intermediates of solandelactone A and B

  摘要：

  A stereocontrolled synthesis of cyclopropyl delta-lactonealdehydes and dodecyl-5-ene-1-yne-3-ol is accomplished with predictable absolute stereochemistry via organocatalytic and catalytic asymmetric transfer hydrogenation reactions. The salient feature of this protocol is the genesis of chirality through an organocatalytic reaction and utilized for installing a critical bifunctional trans-cyclopropane motif, which is a key segment of every representative member of the oxylipin class of natural products such as solandelactone A and B. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.02.008

文献信息

• Leggeri, Paolo; Giacomo, Marcello Di; Azzolina, Ornella, Journal of Chemical Research, Miniprint, 1990, # 11, p. 2759 - 2776
  作者：Leggeri, Paolo、Giacomo, Marcello Di、Azzolina, Ornella、Vercesi, Dina、Pirillo, Demetrio

  DOI：——

  日期：——
• BURGOS, C. E.;NIDY, E. G.;JOHNSON, R. A., TETRAHEDRON LETT., 30,(1989) N8, C. 5081-5084
  作者：BURGOS, C. E.、NIDY, E. G.、JOHNSON, R. A.

  DOI：——

  日期：——
• LEGGERI, PAOLO;DI, GIACOMO MARCELLO;AZZOLINA, ORNELLA;VERCESI, DINA;PIRIL+
  作者：LEGGERI, PAOLO、DI, GIACOMO MARCELLO、AZZOLINA, ORNELLA、VERCESI, DINA、PIRIL+

  DOI：——

  日期：——
• Asymmetric synthesis of the diastereoisomers of the leukotriene B4 antagonist, U-75302
  作者：Carmen E. Burgos、Eldon G. Nidy、Roy A. Johnson

  DOI：10.1016/s0040-4039(01)93452-5

  日期：——
• Enantioselective synthesis of cyclopropyl δ-lactonealdehydes and dodecyl-5-ene-1-yne-3-ol: advanced intermediates of solandelactone A and B
  作者：Gullapalli Kumaraswamy、Gajula Ramakrishna、Balasubramanian Sridhar

  DOI：10.1016/j.tetlet.2011.02.008

  日期：2011.4

  A stereocontrolled synthesis of cyclopropyl delta-lactonealdehydes and dodecyl-5-ene-1-yne-3-ol is accomplished with predictable absolute stereochemistry via organocatalytic and catalytic asymmetric transfer hydrogenation reactions. The salient feature of this protocol is the genesis of chirality through an organocatalytic reaction and utilized for installing a critical bifunctional trans-cyclopropane motif, which is a key segment of every representative member of the oxylipin class of natural products such as solandelactone A and B. (C) 2011 Elsevier Ltd. All rights reserved.