7-(tert-butyldimethylsilanoxy)-1-heptyn-3S-ol | 851012-01-6

• 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: 7-(tert-butyldimethylsilanoxy)-1-heptyn-3S-ol
• 英文别名: 7-[tert-butyl(dimethyl)silyloxy]hept-1-yn-3(S)-ol；(S)-7-((tert-butyldimethylsilyl)oxy)hept-1-yn-3-ol；(3S)-7-[tert-butyl(dimethyl)silyl]oxyhept-1-yn-3-ol
• CAS: 851012-01-6
• 化学式: C₁₃H₂₆O₂Si
• 分子量: 242.434
• InChiKey: MYSANGYXPKPYFN-GFCCVEGCSA-N

物化性质

• 沸点：
  290.8±30.0 °C(Predicted)
• 密度：
  0.908±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.17
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7-(tert-butyldimethylsilanoxy)-1-heptyn-3S-ol 在 tris-(dibenzylideneacetone)dipalladium(0) 、 四(三苯基膦)钯 、 三苯基膦 、 copper(l) chloride 、 lithium chloride 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 26.0h， 生成 (S,E)-7-((tert-butyldimethylsilyl)oxy)-2-phenyl–1-(trimethylsilyl)hept-1-en-3-ol
  参考文献：
  名称：

  含醛烯丙基钯中间体 Umpolung 环化高非对映选择性和对映选择性的关键因素

  摘要：

  充分研究了两种钯/手性二膦催化的含醛乙酸烯丙酯和丙二烯与芳基硼酸的 umpolung 环化反应，以确定其反应的关键因素。

  DOI：

  10.1246/bcsj.20190167
• 作为产物：
  描述：

  7-((tert-butyldimethylsilyl)oxy)hept-1-yn-3-ol 在 (S)-alpine borane 、 2-碘苯甲酸 作用下， 以 四氢呋喃 为溶剂， 生成 7-(tert-butyldimethylsilanoxy)-1-heptyn-3S-ol
  参考文献：
  名称：

  Chromium(III) catalyzed synthesis of allenes from propargyl derivatives via a carbometalation–elimination sequence

  摘要：

  The syn-carbometalation/syn-elimination of propargyl substrates to form allenes has been achieved using cationic chromium(III) catalysts activated by alkylaluminums. The mechanism and scope of this transformation are presented. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.01.143

文献信息

• An 1,2-Elimination Approach to the Enantioselective Synthesis of 1,3-Disubstituted Linear Allenes
  作者：Yikang Wu、Yan Zhang、Hong-Dong Hao

  DOI：10.1055/s-0029-1219542

  日期：2010.4

  The construction of 1,3-disubstituted allene skeleton, which is present in many natural allenes, via an i-PrMgBr-mediated elimination of optically active 3-acetoxy-2-iodo-prop-1-ene derviatives is exemplified through the enantioselective total synthesis of two bioactive natural allenes.

  1,3-二取代丙二烯骨架的构建，它存在于许多天然丙二烯中，通过 i-PrMgBr 介导的光学活性 3-乙酰氧基-2-碘-丙-1-烯衍生物的消除通过对映选择性总合成两种具有生物活性的天然丙二烯。
• Enantioselective synthesis of methyl-5(R)-fluorohept-6-ynoate
  作者：Vijaya Lingam Manthati、A. Sai Krishna Murthy、Frédéric Caijo、Delphine Drouin、Philippe Lesot、Danielle Grée、René Grée

  DOI：10.1016/j.tetasy.2006.08.010

  日期：2006.9

  The asymmetric synthesis of propargylic fluorides, (+)-6 and (+)-3 with ee's > 95%, is reported. The first key step involves an asymmetric transfer hydrogenation of the propargylic ketone 11, using Noyori's catalyst, to give alcohol (+)-10. The second important step is the highly stereoselective DAST mediated fluorination of the propargylic alcohol (-)-5. The ee determinations were performed using both NMR in chiral solvents and chiral GC. These propargylic fluorides appear to be useful intermediates in the preparation of fluorinated analogues of bioactive chiral molecules. (c) 2006 Elsevier Ltd. All rights reserved.
• Chromium(III) catalyzed synthesis of allenes from propargyl derivatives via a carbometalation–elimination sequence
  作者：Gary A. Molander、Erin M. Sommers

  DOI：10.1016/j.tetlet.2005.01.143

  日期：2005.3

  The syn-carbometalation/syn-elimination of propargyl substrates to form allenes has been achieved using cationic chromium(III) catalysts activated by alkylaluminums. The mechanism and scope of this transformation are presented. (c) 2005 Elsevier Ltd. All rights reserved.
• Key Factors for High Diastereo- and Enantioselectivity of Umpolung Cyclizations of Aldehyde-Containing Allylpalladium Intermediates
  作者：Hirokazu Tsukamoto、Ayumu Kawase、Hirotaka Omura、Takayuki Doi

  DOI：10.1246/bcsj.20190167

  日期：2019.10.15

  Two palladium/chiral diphosphine-catalyzed umpolung cyclizations of aldehyde-containing allylic acetates and allenes with arylboronic acid are fully investigated to establish key factors in their h...

  充分研究了两种钯/手性二膦催化的含醛乙酸烯丙酯和丙二烯与芳基硼酸的 umpolung 环化反应，以确定其反应的关键因素。