(2E)-1-(Benzyloxymethyloxy)-2-butenyl(tri-n-butyl)stannane | 133319-48-9

• 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: (2E)-1-(Benzyloxymethyloxy)-2-butenyl(tri-n-butyl)stannane
• 英文别名: tributyl-[(E,1R)-1-(phenylmethoxymethoxy)but-2-enyl]stannane
• CAS: 133319-48-9；124664-82-0；133145-76-3
• 化学式: C₂₄H₄₂O₂Sn
• 分子量: 481.306
• InChiKey: FITAAXUNQNJJML-KHLYBYSVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.51
• 重原子数：
  27.0
• 可旋转键数：
  16.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (2E)-1-(Benzyloxymethyloxy)-2-butenyl(tri-n-butyl)stannane 在 sodium tetrahydroborate 、 sodium periodate 、 四氧化锇 、 十二/十四烷基二甲基氧化胺 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (R)-2-Benzyloxymethoxy-2-[(2R,4S,5R)-4-methyl-5-phenyl-3-(toluene-4-sulfonyl)-oxazolidin-2-yl]-ethanol
  参考文献：
  名称：

  Addition of racemic alkoxyallylstannanes to an enantiomerically pure 2-methoxyoxazolidine: an example of combined mutual diastereoface selection and kinetic resolution

  摘要：

  The BF3.Et2O-promoted addition of racemic alpha- and gamma-alkoxyallylstannanes 2 or 3 to the 2-methoxyoxazolidine 1 afforded adducts 4 and 5 in diastereomeric ratios up to 95:5 accompanied by enantioenriched gamma-stannanes (R)-3. This behavior is consistent with a fast alpha-to-gamma rearrangement of the alkoxystannanes followed by an enantiomer- as well as mutual diastereoface-discriminating condensation.

  DOI：

  10.1021/jo00025a001

文献信息

• Remarkable increase in the diastereofacial selectivity of the addition of β-methyl α-(alkoxy)allylstannane to aldehydes: substituent effects on diastereofacial selectivity
  作者：Benjamin W Gung、Daniel T Smith、Mark A Wolf

  DOI：10.1016/s0040-4039(00)71205-6

  日期：1991.1

  Several new chiral allylstannanes were prepared and reacted with aldehydes. Excellent diastereofacial selectivity was observed for the reactions of allylstannane 1 with aldehydes in the presence of BF3·Et2O. This is in contrast to the results from other allylstannanes which do not bear a β-methyl group. These observations were rationalized based on a combination of steric and electronic effects.

  制备了几种新的手性烯丙基锡烷，并与醛反应。在存在BF 3 ·Et 2 O的情况下，烯丙基锡烷1与醛的反应具有极好的非对映选择性，这与其他不带有β-甲基基团的烯丙基锡的结果相反。这些观察是基于空间和电子效应的组合而合理化的。
• An anomalous case of diastereofacial selectivity in the addition of chiral allylstannanes to benzaldehyde: is the “inside alkoxy” effect involved?
  作者：Benjamin W. Gung、Andrew J. Peat、Barbara M. Snook、Daniel T. Smith

  DOI：10.1016/s0040-4039(00)79466-4

  日期：1991.1

  The “inside alkosy” effect has been found to be important in the addition of α-(alkoxy) allylstannanes to aldehydes in the presence of BF3·Et2O.

  发现在BF 3 ·Et 2 O存在的情况下，向醛中添加α-（烷氧基）烯丙基锡烷酸酯时，“内部烷氧基”效应很重要。
• Evidence for Synclinal Transition State in the Reactions of Aromatic Aldehydes with α-(Alkoxy)allylstannanes
  作者：Benjamin W. Gung、Daniel T. Smith、Mark A. Wolf

  DOI：10.1016/s0040-4020(01)88299-5

  日期：1992.1

  Unlike aliphatic aldehydes, aromatic aldehydes produce greater than 95% of syn-(Z) enol ether when treated with alpha-(alkoxy)allylstannanes in the presence of BF3.Et2O. However, in the presence of TiCl4, the reaction of p-chloro-o-methoxybenzaldehyde with alpha-(alkoxy)crotylstannane produced predominantly the syn-(E) isomer.
• Regio- and Diastereofacial Selective Hydroboration of Chiral Allylic Stannanes, Silanes, and Germanes
  作者：Benjamin W. Gung、Keith W. Ohm、Daniel T. Smith

  DOI：10.1080/00397919408013815

  日期：1994.1

  Hydroboration of the chiral allylic metals (1a-1e) gave regiospecifically 1,3-diol. Greater than 95% of syn-1,3-diol was obtained with 9-BBN, while a 50:50 mixture of syn and anti-1,3-diol was produced with BH3. The chiral allylic alcohol, 2,2-dimethyl-4-hexen-3-ol (1f), produced anti-1,2-diol.
• MARSHALL, JAMES A.;GUNG, WEI YI, TETRAHEDRON LETT., 30,(1989) N7, C. 2183-2186
  作者：MARSHALL, JAMES A.、GUNG, WEI YI

  DOI：——

  日期：——