(Z)-9-[tri(ethoxy)silyl]cycloheptadec-9-en-one

• 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: (Z)-9-[tri(ethoxy)silyl]cycloheptadec-9-en-one
• 英文别名: (Z)-9-[(triethoxysilyl)]-cycloheptadec-9-en-1-one；(9Z)-9-triethoxysilylcycloheptadec-9-en-1-one
• 化学式: C₂₃H₄₄O₄Si
• 分子量: 412.685
• InChiKey: CTDVZTNPUPLXPJ-ATJXCDBQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.54
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (Z)-9-[tri(ethoxy)silyl]cycloheptadec-9-en-one 在 水 、 silver fluoride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 3.0h， 以70%的产率得到trans-9-Cycloheptadecen-1-one
  参考文献：
  名称：

  A chemo- and stereoselective reduction of cycloalkynes to (E)-cycloalkenes

  摘要：

  本文描述了通过选择性合成(E)-环烷烯的一种立体选择性途径，该途径包括合适的二炔的环化炔类歧化反应（RCAM），随后是以钌为催化剂的所形成的环炷选择性反式加氢硅烷化反应，最后是通过AgF介导的得到的乙烯基硅烷的去硅烷化反应。

  DOI：

  10.1039/b207169j
• 作为产物：
  描述：

  2,19-heneicosadiyn-11-one 在 Tris(t-butoxy)(2,2-dimethylpropylidyne)tungsten(VI), 98% Schrock Alkyne Metathesis Catalyst 、 tris(acetonitrile)pentamethylcyclopentadienylruthenium(II) hexafluorophosphate 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 0.75h， 生成 (Z)-9-[tri(ethoxy)silyl]cycloheptadec-9-en-one
  参考文献：
  名称：

  (E)-Cycloalkenes and (E,E)-cycloalkadienes by ring closing diyne- or enyne–yne metathesis/semi-reduction

  摘要：

  A concise, practical and stereoselective entry into macrocyclic (E)-alkenes is outlined comprising a sequence of ring closing alkyne metathesis (RCAM), trans-selective hydrosilylation of the resulting cycloalkynes catalyzed by [Cp*Ru(MeCN)(3)]PF6, and a protodesilylation of the ensuing vinylsilanes with AgF in aq. THF/MeOH. Moreover, the first examples of intramolecular enyne-yne metathesis reactions catalyzed by the Schrock alkylidyne complex (tBUO)(3)W drop CCMe3 are reported; the resulting cyclic enynes can be converted along similar lines into the corresponding (E,E)-configured 1,3-dienes in good overall yields. Cycloalkyne 4 and the (E)-configured cyclic olefins 6 and 21 were characterized by X-ray crystallography. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.05.042

文献信息

• A chemo- and stereoselective reduction of cycloalkynes to (E)-cycloalkenes
  作者：Alois Fürstner、Karin Radkowski

  DOI：10.1039/b207169j

  日期：——

  A stereoselective entry into (E)-cycloalkenes is described, comprising the ring closing alkyne metathesis (RCAM) of suitable diynes, a ruthenium-catalyzed trans-selective hydrosilylation of the cycloalkynes thus formed, followed by a desilylation of the resulting vinylsilanes mediated by AgF.

  本文描述了通过选择性合成(E)-环烷烯的一种立体选择性途径，该途径包括合适的二炔的环化炔类歧化反应（RCAM），随后是以钌为催化剂的所形成的环炷选择性反式加氢硅烷化反应，最后是通过AgF介导的得到的乙烯基硅烷的去硅烷化反应。
• (E)-Cycloalkenes and (E,E)-cycloalkadienes by ring closing diyne- or enyne–yne metathesis/semi-reduction
  作者：Fabrice Lacombe、Karin Radkowski、Günter Seidel、Alois Fürstner

  DOI：10.1016/j.tet.2004.05.042

  日期：2004.8

  A concise, practical and stereoselective entry into macrocyclic (E)-alkenes is outlined comprising a sequence of ring closing alkyne metathesis (RCAM), trans-selective hydrosilylation of the resulting cycloalkynes catalyzed by [Cp*Ru(MeCN)(3)]PF6, and a protodesilylation of the ensuing vinylsilanes with AgF in aq. THF/MeOH. Moreover, the first examples of intramolecular enyne-yne metathesis reactions catalyzed by the Schrock alkylidyne complex (tBUO)(3)W drop CCMe3 are reported; the resulting cyclic enynes can be converted along similar lines into the corresponding (E,E)-configured 1,3-dienes in good overall yields. Cycloalkyne 4 and the (E)-configured cyclic olefins 6 and 21 were characterized by X-ray crystallography. (C) 2004 Elsevier Ltd. All rights reserved.