(Z)-6-[tert-butyl(dimethyl)silyl]oxy-2,2-dimethyl-1-phenylmethoxy-5-(trimethylsilylmethyl)hex-5-en-3-ol | 464186-78-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (Z)-6-[tert-butyl(dimethyl)silyl]oxy-2,2-dimethyl-1-phenylmethoxy-5-(trimethylsilylmethyl)hex-5-en-3-ol
• CAS: 464186-78-5
• 化学式: C₂₅H₄₆O₃Si₂
• 分子量: 450.809
• InChiKey: BYEFEINGPKGLEL-PYCFMQQDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.22
• 重原子数：
  30
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-6-[tert-butyl(dimethyl)silyl]oxy-2,2-dimethyl-1-phenylmethoxy-5-(trimethylsilylmethyl)hex-5-en-3-ol 在 palladium on activated charcoal 三甲基氯硅烷 、 N-甲基吲哚酮 、 四丙基高钌酸铵 、 四丁基氟化铵 、 氢气 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 生成 (R)-5-(1-(benzyloxy)-2-methylpropan-2-yl)-3-methylfuran-2(5H)-one
  参考文献：
  名称：

  Concise and stereocontrolled synthesis of the southern γ-butyrolactone subunit of polycavernoside A

  摘要：

  The southern gamma -butyrolactone subunit 8 of polycavernoside A was readily assembled by a novel and connective methodology involving an initial ene-reaction followed by an intramolecular oxidative cyclisation. (C) 2000 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(00)01839-6
• 作为产物：
  描述：

  3-(苄氧基)-2,2-二甲基-1-丙醇 在 CuCl*Phen 4-二甲氨基吡啶 、 偶氮二甲酸二苄酯 、 氧气 、 氯化二乙基铝 作用下， 以 氟苯 、 二氯甲烷 为溶剂， 生成 (Z)-6-[tert-butyl(dimethyl)silyl]oxy-2,2-dimethyl-1-phenylmethoxy-5-(trimethylsilylmethyl)hex-5-en-3-ol
  参考文献：
  名称：

  Concise and stereocontrolled synthesis of the southern γ-butyrolactone subunit of polycavernoside A

  摘要：

  The southern gamma -butyrolactone subunit 8 of polycavernoside A was readily assembled by a novel and connective methodology involving an initial ene-reaction followed by an intramolecular oxidative cyclisation. (C) 2000 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(00)01839-6

文献信息

• Tandem Ene-Reaction/Intramolecular Sakurai Cyclisation (IMSC): A Novel Access to Polysubstituted Tetrahydropyrans and γ-Butyrolactones Using a Unique Allylation Strategy
  作者：István E. Markó、Raphaël Dumeunier、Cédric Leclercq、Bernard Leroy、Jean-Marc Plancher、Abdelaziz Mekhalfia、Daniel J. Bayston

  DOI：10.1055/s-2002-28506

  日期：——

  The ene-reaction between a variety of aldehydes and allylsilane 22 generates highly functionalised homoallylic alcohols 23. These adducts undergo a subsequent Intramolecular Sakurai Cyclisation (IMSC), affording in good yields polysubstituted tetrahydropyran derivatives. Furthermore, oxidative desilylation of 23 provides an efficient, connective access to a range of γ-butyrolactones and α-methylene-γ-butyrolactones.

  各种醛和烯丙基硅烷 22 之间的烯反应生成高度官能化的均烯丙基醇 23。这些加合物在随后的分子内樱井环化（IMSC）反应中，可以得到收率很高的多取代四氢吡喃衍生物。此外，对 23 进行氧化脱硅处理，可以高效地连接到一系列 δ³ 丁内酯和 δ±-亚甲基-δ³-丁内酯。
• Concise and stereocontrolled synthesis of the southern γ-butyrolactone subunit of polycavernoside A
  作者：Raphaël Dumeunier、István E Markó

  DOI：10.1016/s0040-4039(00)01839-6

  日期：2000.12

  The southern gamma -butyrolactone subunit 8 of polycavernoside A was readily assembled by a novel and connective methodology involving an initial ene-reaction followed by an intramolecular oxidative cyclisation. (C) 2000 Published by Elsevier Science Ltd.