(E)-dimethyl(phenyl)(1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-2-en-2-yl)silane | 1187817-15-7

• 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)-dimethyl(phenyl)(1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-2-en-2-yl)silane
• 英文别名: dimethyl-phenyl-[(E)-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-2-en-2-yl]silane
• CAS: 1187817-15-7
• 化学式: C₁₈H₂₉BO₂Si
• 分子量: 316.324
• InChiKey: OEQMWVKVZCJEQB-OVCLIPMQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.18
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-dimethyl(phenyl)(1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-2-en-2-yl)silane 、 4-氯苯甲醛 在 双二苯基膦甲烷 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 18.0h， 以97%的产率得到
  参考文献：
  名称：

  Construction of Homoallylic Alcohols from Terminal Alkynes and Aldehydes with Installation of syn-Stereochemistry

  摘要：

  A cationic rhodium(I) catalyst turns 2-silyl-1-alkenylboronate, readily prepared from a terminal alkyne, into the corresponding allylboronate species, which immediately undergoes nucleophilic addition to an aldehyde to give a syn-homoallylic alcohol stereoselectively.

  DOI：

  10.1021/ja502169d
• 作为产物：
  描述：

  在 bisacetonitrile[norbornadiene]rhodium(I) hexafluoroantimonate 、 双二苯基膦甲烷 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 10.0h， 生成 (E)-dimethyl(phenyl)(1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-2-en-2-yl)silane
  参考文献：
  名称：

  Construction of Homoallylic Alcohols from Terminal Alkynes and Aldehydes with Installation of syn-Stereochemistry

  摘要：

  A cationic rhodium(I) catalyst turns 2-silyl-1-alkenylboronate, readily prepared from a terminal alkyne, into the corresponding allylboronate species, which immediately undergoes nucleophilic addition to an aldehyde to give a syn-homoallylic alcohol stereoselectively.

  DOI：

  10.1021/ja502169d

文献信息

• Iron-Catalyzed 1,4-Hydroboration of 1,3-Dienes
  作者：Jessica Y. Wu、Benoît Moreau、Tobias Ritter

  DOI：10.1021/ja9048493

  日期：2009.9.16

  A chemo-, regio-, and stereoselective iron-catalyzed 1,4-hydroboration of dienes that affords gamma-disubstituted allylboranes has been developed. 1,4-Hydroboration of 2-substituted dienes forms allylborane products with (E)-trisubstituted double bonds exclusively.
• Construction of Homoallylic Alcohols from Terminal Alkynes and Aldehydes with Installation of <i>syn</i>-Stereochemistry
  作者：Tomoya Miura、Yui Nishida、Masahiro Murakami

  DOI：10.1021/ja502169d

  日期：2014.4.30

  A cationic rhodium(I) catalyst turns 2-silyl-1-alkenylboronate, readily prepared from a terminal alkyne, into the corresponding allylboronate species, which immediately undergoes nucleophilic addition to an aldehyde to give a syn-homoallylic alcohol stereoselectively.