(Z)-3-phenylthio-1-trimethylsilyloct-5-en-1-yne | 452973-00-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (Z)-3-phenylthio-1-trimethylsilyloct-5-en-1-yne
• 英文别名: trimethyl-[(Z)-3-phenylsulfanyloct-5-en-1-ynyl]silane
• CAS: 452973-00-1
• 化学式: C₁₇H₂₄SSi
• 分子量: 288.529
• InChiKey: QWALZCMCMVITGL-VURMDHGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.38
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (Z)-3-phenylthio-1-trimethylsilyloct-5-en-1-yne 在 四(三苯基膦)钯 哌啶 、 sodium hydroxide 、 copper(l) iodide 、 copper diacetate 、 苄基三乙基氯化铵 、 碳酸氢钠 、 silver nitrate 、 间氯过氧苯甲酸 、 锌 作用下， 以 甲醇 、 二氯甲烷 、 水 、 甲苯 、 乙腈 为溶剂， 反应 71.0h， 生成 (9Z,13Z)-1-t-butyldimethylsilyloxyhexadeca-7,9,11,13-tetraene
  参考文献：
  名称：

  Electrocyclic processes in aromatic biosynthesis: a biomimetic study of pseudorubrenoic acid A

  摘要：

  The possible involvement of 6pi electrocyclic ring closures, mediated by electrocyclase enzymes, of polyunsaturated acyclic polyketide intermediates in the biosynthesis of certain o-dialkyl-substituted benzenoid natural products is discussed. The feasibility of the process is illustrated by the electrocyclic ring closure of 7E,9Z,11E,13Z-1-t-butyldimethylsilyloxy-hexadeca-7,9,1 1,13-tetraene (12a) to the cyclohexadiene 13 followed by dehydrogenation to the analogue 14 of the o-dialkyl-substituted aromatic metabolite pseudorubrenoic acid A (1). (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00320-4
• 作为产物：
  描述：

  (Z)-1-Bromo-2-pentene 、 [[3-(trimethylsilyl)-2-propyn-1-yl]thio]benzene 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 为溶剂， 反应 2.17h， 以75%的产率得到(Z)-3-phenylthio-1-trimethylsilyloct-5-en-1-yne
  参考文献：
  名称：

  Electrocyclic processes in aromatic biosynthesis: a biomimetic study of pseudorubrenoic acid A

  摘要：

  The possible involvement of 6pi electrocyclic ring closures, mediated by electrocyclase enzymes, of polyunsaturated acyclic polyketide intermediates in the biosynthesis of certain o-dialkyl-substituted benzenoid natural products is discussed. The feasibility of the process is illustrated by the electrocyclic ring closure of 7E,9Z,11E,13Z-1-t-butyldimethylsilyloxy-hexadeca-7,9,1 1,13-tetraene (12a) to the cyclohexadiene 13 followed by dehydrogenation to the analogue 14 of the o-dialkyl-substituted aromatic metabolite pseudorubrenoic acid A (1). (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00320-4

文献信息

• Electrocyclic processes in aromatic biosynthesis: a biomimetic study of pseudorubrenoic acid A
  作者：Rodney W Rickards、Danielle Skropeta

  DOI：10.1016/s0040-4020(02)00320-4

  日期：2002.5

  The possible involvement of 6pi electrocyclic ring closures, mediated by electrocyclase enzymes, of polyunsaturated acyclic polyketide intermediates in the biosynthesis of certain o-dialkyl-substituted benzenoid natural products is discussed. The feasibility of the process is illustrated by the electrocyclic ring closure of 7E,9Z,11E,13Z-1-t-butyldimethylsilyloxy-hexadeca-7,9,1 1,13-tetraene (12a) to the cyclohexadiene 13 followed by dehydrogenation to the analogue 14 of the o-dialkyl-substituted aromatic metabolite pseudorubrenoic acid A (1). (C) 2002 Elsevier Science Ltd. All rights reserved.