t-butyldimethylsilyl (Z)-3-phenyl-4-pentenyl ether

• 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: t-butyldimethylsilyl (Z)-3-phenyl-4-pentenyl ether
• 英文别名: (Z)-5-(tert-butyldimethylsilyloxy)-1-phenylpent-1-ene；t-butyldimethylsilyl (Z)-5-phenyl-4-pentenyl ether；(Z)-tert-butyldimethyl((5-phenylpent-4-en-1-yl)oxy)silane；tert-butyl-dimethyl-[(Z)-5-phenylpent-4-enoxy]silane
• 化学式: C₁₇H₂₈OSi
• 分子量: 276.494
• InChiKey: NXPFZIVAJZEHHA-UVTDQMKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  5-苯基-4-戊炔-1-醇 在 咪唑 、 copper(II) acetate monohydrate 、 叔丁醇 、 (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(bis(3,5-bis(trifluoromethyl)phenyl)phosphine) 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 t-butyldimethylsilyl (Z)-3-phenyl-4-pentenyl ether
  参考文献：
  名称：

  使用硅烷和醇对铜进行非极性碳-碳多重键的铜催化高选择性半氢化反应

  摘要：

  发现带有合适的Xantphos衍生物或NHC配体的铜催化剂对于使用硅烷和醇的混合物作为还原剂的非极性不饱和化合物的选择性半氢化反应非常有效。该催化体系可用于内部炔烃选择性半氢化为（Z）-烯烃，同时抑制过度还原为相应的烷烃。此外，还可以选择性地实现末端炔烃，1,2-二烯，1,3-二烯，1,3-烯炔和1,3-二炔体系的半氢化反应。

  DOI：

  10.1002/adsc.201200200

文献信息

• <i>Z</i> ‐Selective Copper(I)‐Catalyzed Alkyne Semihydrogenation with Tethered Cu–Alkoxide Complexes
  作者：Felix Pape、Niklas O. Thiel、Johannes F. Teichert

  DOI：10.1002/chem.201501739

  日期：2015.11.2

  A highly stereoselective alkyne semihydrogenation with copper(I) complexes is reported. Copper–N‐heterocyclic carbene complex catalysts, bearing an intramolecular CuO bond, allow for the direct transfer of both hydrogen atoms from dihydrogen to the alkyne. The corresponding alkenes can be isolated with high Z selectivity and negligible overreduction to the alkane.

  报道了具有铜（I）配合物的高度立体选择性炔烃半氢化。带有分子内CuO键的铜-N-杂环卡宾络合物催化剂可将两个氢原子直接从二氢转移至炔烃。可以以高的Z选择性和相对于烷烃的过量还原可以忽略的方式分离相应的烯烃。
• Titanium-Mediated Carboxylation of Alkynes With Carbon Dioxide
  作者：Yvan Six

  DOI：10.1002/ejoc.200390170

  日期：2003.3

  The regioselective carboxylation of nonactivated internal alkynes can be performed with carbon dioxide under atmospheric pressure using a simple procedure based on the chemistry of Sato-type diisopropyloxytitanacyclopropenes. Various polysubstituted vinylcarboxylic acids and butenolides can be prepared in this way. In addition, this paper describes an experimental protocol for the preparation of solutions

  未活化的内部炔烃的区域选择性羧化可以在大气压下使用二氧化碳进行，使用基于 Sato 型二异丙氧基钛环丙烯化学的简单程序。各种多取代的乙烯基羧酸和丁烯内酯可以通过这种方式制备。此外，本文还介绍了制备（η2-环戊烯）二异丙氧基钛溶液的实验方案。该复合物还与二氧化碳反应，并介导苯乙酮的频哪醇偶联。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)
• The reaction of dialkoxytitanacyclopropanes and dialkoxytitanacyclopropenes with carbon dioxide
  作者：Yvan Six

  DOI：10.1039/b201527g

  日期：2002.4.26

  Dialkoxytitanacyclopropanes and dialkoxytitanacyclopropenes react with one molecule of carbon dioxide to afford diversely substituted carboxylic acids after hydrolysis.

  二烷氧基钛杂环丙烷和二烷氧基钛杂环丙烯与一分子二氧化碳发生反应，水解后生成多种取代的羧酸。
• <i>Trans</i>-Hydrometalation of Alkynes by a Combination of InCl₃ and DIBAL-H:  One-Pot Access to Functionalized <i>(Z)</i>-Alkenes
  作者：Kazuaki Takami、Hideki Yorimitsu、Koichiro Oshima

  DOI：10.1021/ol026401w

  日期：2002.8.1

  Triethylborane-induced hydrometalation of alkynes proceeds in an anti manner to afford the corresponding (Z)-alkenylmetal compounds stereoselectively, where dichloroindium hydride would play a key role. A variety of functional groups including hydroxy, carbonyl, and carboxy groups were tolerant under the reaction conditions. Following iodolysis and cross-coupling reaction of the (Z)-alkenylmetal species show the usefulness of this strategy.
• Triethylborane-Mediated Hydrogallation and Hydroindation:  Novel Access to Organogalliums and Organoindiums
  作者：Kazuaki Takami、Satoshi Mikami、Hideki Yorimitsu、Hiroshi Shinokubo、Koichiro Oshima

  DOI：10.1021/jo0344790

  日期：2003.8.1

  Hydrogallation of carbon-carbon multiple bonds proceeds in the presence of triethylborane as a radical initiator. Several functionalities do not interfere with this reaction. Resulting alkenyl- and alkylgallium species can be trapped by several electrophiles. Highly regioselective radical addition of an indium hydride reagent to alkynes is also achieved. Various functionalities are tolerant under the reaction conditions. The reaction proceeds with complete anti stereoselectivity. Alkenylindiums obtained via hydroindation can be employed for the following cross-coupling reaction with aryl halides in one pot.