(E)-2-[3-(Trimethylsilyl)-2-propynylidene]-cyclopentanone | 128878-86-4

• 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-[3-(Trimethylsilyl)-2-propynylidene]-cyclopentanone
• 英文别名: (2E)-2-(3-trimethylsilylprop-2-ynylidene)cyclopentan-1-one
• CAS: 128878-86-4
• 化学式: C₁₁H₁₆OSi
• 分子量: 192.333
• InChiKey: NQSQFBMOHALGAH-JXMROGBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.55
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-2-[3-(Trimethylsilyl)-2-propynylidene]-cyclopentanone 以 丙酮 为溶剂， 反应 2.0h， 以41%的产率得到(Z)-2-[3-(Trimethylsilyl)-2-propynylidene]-cyclopentanone
  参考文献：
  名称：

  Synthetic studies on the compounds related to neocarzinostatin chromophore. 1. Synthesis of the acyclic (E)- and (Z)-dienediyne systems

  摘要：

  The stereo-defined (E)- and (Z)-dienediyne systems related to neocarzinostatin chromophore (1) could be prepared by the coupling reaction of (E)- and (Z)-enol triflates with optically active acetylynes hearing the correct absolute stereochemistries as found in 1. Comparison of cytotoxic level of the (E)- and (Z)-dienediyne diols (32 and 33) revealed that the stereochemistry of exo-trisubstituted double bond might have a posibility to control the cytotoxicity of the acyclic analogues related to I.

  DOI：

  10.1016/s0040-4020(01)88124-2
• 作为产物：
  描述：

  (Z)-2-(hydroxymethylene)cyclopentan-1-one 在 copper(l) iodide 、 四(三苯基膦)钯 、 叔丁基锂 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 0.59h， 生成 (E)-2-[3-(Trimethylsilyl)-2-propynylidene]-cyclopentanone
  参考文献：
  名称：

  Stereoselective synthesis of (Z)-ketoeneynes via Pd(0)-Cu(I)-catalyzed cross-coupling of (Z)-ketoenol triflate with 1-alkynes

  摘要：

  A general and stereoselective synthesis of (Z)-ketoeneynes 9 and 11a-f was established by using a Pd(O)-Cu(I)-catalyzed cross-coupling of the labile (Z)-ketoenol triflate 3 with 1-alkynes under carefully controlled reaction conditions. Isomerization of the coupling products into the more stable (E)-ketoeneynes 8 and 12a-f was observed and could be minimized by earring out the coupling reaction in CH3CN at low temperature using Et3N as the base. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00610-8

文献信息

• Contrasteric regioselectivity of palladium(O) catalyzed couplings of alkynes with a bis(enoltriflate). Novel syntheses of E-configurated dienediynes
  作者：Jean Suffert、Anke Eggers、Stefan W. Scheuplein、Reinhard Brückner

  DOI：10.1016/s0040-4039(00)60521-x

  日期：1993.6

  Two consecutive PdCl2(PPh3)2 catalYzed couPlings of the bis(enoltriflate) E-2 with two different alkynes were performed as one-pot reactions; they provided 3:1-7:1 mixtures of dienediynes E-3a'-l' and E-3a-l in 48-91 % yield. Selective syntheses of such dienediynes were achieved by Pd mediated couplings of enolnonaflate E-6 with an alkyne followed by addition of a lithium acetylide and by dehydration.
• Synthesis and cytotoxicity of the acyclic (E)- and (Z)-dienediyne systems related to neocarzinostatine chromophore
  作者：Kazuhiko Nakatani、Katsuko Arai、Noriaki Hirayama、Fuyuhiko Matsuda、Shiro Terashima

  DOI：10.1016/0040-4039(90)80218-b

  日期：1990.1
• NAKATANI, KAZUHIKO;ARAI, KATSUKO;HIRAYAMA, NORIAKI;MATSUDA, FUYUHIKO;TERA+, TETRAHEDRON LETT., 31,(1990) N6, C. 2323-2326
  作者：NAKATANI, KAZUHIKO、ARAI, KATSUKO、HIRAYAMA, NORIAKI、MATSUDA, FUYUHIKO、TERA+

  DOI：——

  日期：——
• Stereoselective synthesis of (Z)-ketoeneynes via Pd(0)-Cu(I)-catalyzed cross-coupling of (Z)-ketoenol triflate with 1-alkynes
  作者：Wei-Min Dai、Jinlong Wu

  DOI：10.1016/s0040-4020(97)00610-8

  日期：1997.7

  A general and stereoselective synthesis of (Z)-ketoeneynes 9 and 11a-f was established by using a Pd(O)-Cu(I)-catalyzed cross-coupling of the labile (Z)-ketoenol triflate 3 with 1-alkynes under carefully controlled reaction conditions. Isomerization of the coupling products into the more stable (E)-ketoeneynes 8 and 12a-f was observed and could be minimized by earring out the coupling reaction in CH3CN at low temperature using Et3N as the base. (C) 1997 Elsevier Science Ltd.
• Synthetic studies on the compounds related to neocarzinostatin chromophore. 1. Synthesis of the acyclic (E)- and (Z)-dienediyne systems
  作者：Kazuhiko Nakatani、Katsuko Arai、Noriaki Hirayama、Fuyuhiko Matsuda、Shiro Terashima

  DOI：10.1016/s0040-4020(01)88124-2

  日期：——

  The stereo-defined (E)- and (Z)-dienediyne systems related to neocarzinostatin chromophore (1) could be prepared by the coupling reaction of (E)- and (Z)-enol triflates with optically active acetylynes hearing the correct absolute stereochemistries as found in 1. Comparison of cytotoxic level of the (E)- and (Z)-dienediyne diols (32 and 33) revealed that the stereochemistry of exo-trisubstituted double bond might have a posibility to control the cytotoxicity of the acyclic analogues related to I.