(E)-2-(Trimethylsilyl)-2-hepten-1-ol

• 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)-2-(Trimethylsilyl)-2-hepten-1-ol
• 英文别名: (E)-2-trimethylsilylhept-2-en-1-ol
• 化学式: C₁₀H₂₂OSi
• 分子量: 186.37
• InChiKey: ASXAPOAOFGMMLN-CSKARUKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.97
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 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)-2-(Trimethylsilyl)-2-hepten-1-ol 以100%的产率得到
  参考文献：
  名称：

  SATO, FUMIE;TANAKA, YOUICHI;SATO, MASAO, J. CHEM. SOC. CHEM. COMMUN., 1983, N 4, 165-166

  摘要：

  DOI：
• 作为产物：
  描述：

  (E)-2-(Trimethylsilyl)-2-heptenyl pivalate 在 甲基锂 作用下， 以 乙醚 为溶剂， 以87%的产率得到(E)-2-(Trimethylsilyl)-2-hepten-1-ol
  参考文献：
  名称：

  Chromium(II)-Mediated Stereodivergent Additions of Allylic Phosphates and Halides to Aldehydes

  摘要：

  The addition of gamma-disubstituted allylchromium(III) reagents to aldehydes proceeds in a stereodivergent manner, in contrast to the case of gamma-monosubstituted allylchromium(III) species. The method allows the preparation of a variety of homoallylic alcohols bearing a quaternary center of defined relative configuration in the alpha-position. The preparation of both stereomeric homoallylic alcohols 13 is possible by using either of the two (E)- or (Z)-allylic precursors. The reaction has been extended to a gamma-monosubstituted beta-(trimethylsilyl)allylic system. The intermediate allylic chromium(III) reagents can be conveniently prepared from the corresponding phosphates (or chlorides) in DMPU or THF in the presence of catalytic amounts of LiI.

  DOI：

  10.1021/jo00114a026

文献信息

• A regiodefined synthesis of α-trimethylsilyl ketones catalyzed by rhodium(I) hydride complex
  作者：Susumu Sato、Isamu Matsuda、Yusuke Izumi

  DOI：10.1016/0022-328x(88)80214-6

  日期：1988.4

  Regiodefined synthesis of α-trimethylsilyl ketones is attained by one of three different routes: isomerization of β-trimethylsilyl allyl alcohols (route A), isomerization of β′-trimethylsilyl allyl alcohols (route B), and dehydrogenation of β-trimethylsilyl alcohols via transfer hydrogenation to α,β-enones (route C). All of these procedures are catalyzed efficiently by HRh(PPh3)4 at about 100 °C. Route

  通过以下三种途径之一实现区域定义的α-三甲基硅烷基酮的合成：β-三甲基硅烷基烯丙醇的异构化（途径A），β'-三甲基硅烷基烯丙醇的异构化（途径B）和β-三甲基硅烷基醇通过转移脱氢氢化成α，β-烯酮（路线C）。所有这些步骤均在大约100°C下被HRh（PPh 3）4有效地催化。路线A不可避免地需要存在2-三甲基甲硅烷基-1-苯基-2-丙烯-1-酮作为平滑异构化的助催化剂。这有力地表明，一种分子间转移氢化在催化循环中起着重要的作用。
• SATO, FUMIE;TANAKA, YOUICHI;KANBARA, HIROSHI, J. CHEM. SOC. CHEM. COMMUN., 1983, N 18, 1024-1025
  作者：SATO, FUMIE、TANAKA, YOUICHI、KANBARA, HIROSHI

  DOI：——

  日期：——
• SATO, SUSUMU;MATSUDA, ISAMU;IZUMI, YUSUKE, J. ORGANOMET. CHEM., 344,(1988) N 1, 71-88
  作者：SATO, SUSUMU、MATSUDA, ISAMU、IZUMI, YUSUKE

  DOI：——

  日期：——
• Chromium(II)-Mediated Stereodivergent Additions of Allylic Phosphates and Halides to Aldehydes
  作者：Stefan Nowotny、Charles E. Tucker、Carole Jubert、Paul Knochel

  DOI：10.1021/jo00114a026

  日期：1995.5

  The addition of gamma-disubstituted allylchromium(III) reagents to aldehydes proceeds in a stereodivergent manner, in contrast to the case of gamma-monosubstituted allylchromium(III) species. The method allows the preparation of a variety of homoallylic alcohols bearing a quaternary center of defined relative configuration in the alpha-position. The preparation of both stereomeric homoallylic alcohols 13 is possible by using either of the two (E)- or (Z)-allylic precursors. The reaction has been extended to a gamma-monosubstituted beta-(trimethylsilyl)allylic system. The intermediate allylic chromium(III) reagents can be conveniently prepared from the corresponding phosphates (or chlorides) in DMPU or THF in the presence of catalytic amounts of LiI.
• SATO, FUMIE;TANAKA, YOUICHI;SATO, MASAO, J. CHEM. SOC. CHEM. COMMUN., 1983, N 4, 165-166
  作者：SATO, FUMIE、TANAKA, YOUICHI、SATO, MASAO

  DOI：——

  日期：——