三丁基(十一碳-2,3-二烯-4-基)锡烷 | 131043-65-7

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机过渡后金属化合物
• 中文名称: 三丁基(十一碳-2,3-二烯-4-基)锡烷
• 中文别名: 锡烷,三丁基[1-(1-亚丙烯基)辛基]-
• 英文名称: 4-(tributylstannyl)-2,3-undecadiene
• CAS: 131043-65-7；131043-67-9
• 化学式: C₂₃H₄₆Sn
• 分子量: 441.328
• InChiKey: GHENAXCGNTZNAH-UHFFFAOYSA-N

物化性质

• 沸点：
  439.7±28.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.84
• 重原子数：
  24
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  三丁基(十一碳-2,3-二烯-4-基)锡烷 在 四丁基氯化铵 copper(l) iodide 、 tris(dibenzylideneacetone)dipalladium (0) 、 三(2-呋喃基)膦 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 1-(tert-butoxycarbonyl)-2-ethyl-3-heptylindole
  参考文献：
  名称：

  2,3-二取代的吲哚合成的新入口。

  摘要：

  [反应：见正文] N-酰基-2-碘苯胺与1-（三丁基锡烷基）-1-取代的烯的Stille偶联影响了2-甲基-3-取代的吲哚的连续一步形成。或者，另一种类型的2-烷基-3-取代的吲哚可以通过一锅操作合成，该操作由与1-（三丁基锡烷基）-1,3-二取代的烯基的斯蒂勒偶联反应，然后进行TBAF处理组成。该方法可用于吲哚美辛的合成。

  DOI：

  10.1021/ol052179u
• 作为产物：
  描述：

  Toluene-4-sulfonic acid 1-methyl-dec-2-ynyl ester 生成 三丁基(十一碳-2,3-二烯-4-基)锡烷
  参考文献：
  名称：

  MARSHALL, JAMES A.;WANG, XIAO-JUN, J. ORG. CHEM., 55,(1990) N6, C. 6246-6248

  摘要：

  DOI：

文献信息

• Diastereoselective additions of allenylstannanes to aldehydes
  作者：James A. Marshall、Xiao Jun Wang

  DOI：10.1021/jo00313a007

  日期：1990.12

  The allenylstannane 4 undergoes highly syn selective additions to alpha-branched aldehydes 8b and 8c in the presence of BF3.OEt2. With the beta-alkoxy aldehyde 21, Cram-Felkin addition results with BF3.Oet2 as the Lewis acid, whereas MgBr2 leads to chelation-controlled addition.
• Synthesis of syn,syn; anti,syn; syn,anti; and anti,anti Stereotriads from a Single Pair of Enantiomeric Reagents
  作者：James A. Marshall、Jolyon F. Perkins、Mark A. Wolf

  DOI：10.1021/jo00122a041

  日期：1995.9

  The stannanes (S)-1a, (R)-1b, and (S)-1c add to (S)- and (R)-2-methyl-3-(benzyloxy)propanal ((S)-2 and (R)-2) to afford the syn,syn (BF3 . OEt(2) promotion), syn,anti (MgBr2 . OEt(2) promotion), anti,anti (SnCl4-derived reagent in CH2Cl2), and anti,syn (SnCl4-derived reagent in hexane) stereotriad adducts 3, 4, 6, and 7.
• Synthesis of enantioenriched homopropargylic alcohols through diastereoselective SE' additions of chiral allenylstannanes to aldehydes
  作者：James A. Marshall、Xiao Jun Wang

  DOI：10.1021/jo00030a036

  日期：1992.2

  Allenylstannanes (S)-4 and (R)-4, available in ca. 90% ee from alkynones 1 through reduction with the LiAlH4-Darvon alcohol or -ent-Darvon alcohol complex, followed by S(N)2' displacement on the derived mesylates (R)-3 or (S)-3 with Bu3SnLi.CuBr.Me2S, readily add to various aldehydes under Lewis acid catalysis to afford optically active homopropargylic alcohols with good to excellent syn diastereoselectivity. With 2-(benzyloxy)propanal (48), MgBr2-catalyzed reactions are highly stereoselective, affording the syn adduct 49 from the (S)-stannane (S)-4 and the anti adduct 52 from the (R)-stannane (R)-4. BF3-promoted additions give mainly or exclusively the syn adducts 49 and 51. Additions of (S)- and (R)-4 to (R)-3-(benzyloxy)-2-methylpropanal (61) yield the syn adducts 62 and 64 as major or exclusive products.
• Synthesis of Syn and Anti Homopropargylic and Allenic Alcohols through Diastereoselective SE2' Addition of a Common Chiral Allenylstannane Precursor to Aldehydes
  作者：James A. Marshall、Jolyon Perkins

  DOI：10.1021/jo00092a001

  日期：1994.7

  The (tri-n-butylallenyl)stannanes 3 and 17 afford the allenyl adducts 8 and 19 upon brief treatment with stannic chloride and then addition of isobutyraldehyde, whereas preequilibration with SnCl4 and subsequent aldehyde addition leads to the anti homopropargylic adducts 5 and 19.
• MARSHALL, JAMES A.;WANG, XIAO-JUN, J. ORG. CHEM., 55,(1990) N6, C. 6246-6248
  作者：MARSHALL, JAMES A.、WANG, XIAO-JUN

  DOI：——

  日期：——