(E)-1-hexenyldiisopropoxyborane | 91083-27-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硼酸衍生物
• 英文名称: (E)-1-hexenyldiisopropoxyborane
• 英文别名: 1-hexenyldiisopropoxyborane；[(E)-hex-1-enyl]-di(propan-2-yloxy)borane
• CAS: 91083-27-1
• 化学式: C₁₂H₂₅BO₂
• 分子量: 212.14
• InChiKey: JGIYRNITJBYKAM-MDZDMXLPSA-N

物化性质

• 沸点：
  237.1±23.0 °C(Predicted)
• 密度：
  0.829±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.61
• 重原子数：
  15
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 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)-1-hexenyldiisopropoxyborane 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  Hydroboration–azide alkylation as efficient tandem reactions for the synthesis of chiral non racemic substituted pyrrolidines

  摘要：

  The synthesis of chiral non racemic substituted pyrrolidines from homoallylic alcohols is presented. These precursors are readily converted via the azides to the corresponding pyrrolidines using hydroboration-cycloalkylation tandem reactions as key steps. (C) 1998 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0022-328x(98)00665-2
• 作为产物：
  描述：

  diisopropyl (Z)-1-hexenylboronate 以 正己烷 为溶剂， 生成 (E)-1-hexenyldiisopropoxyborane
  参考文献：
  名称：

  有机oboranes。37.（Z）-1-烯基硼酸酯的合成与性质

  摘要：

  DOI：

  10.1021/om00087a013

文献信息

• Enantioselective Multicomponent Condensation Reactions of Phenols, Aldehydes, and Boronates Catalyzed by Chiral Biphenols
  作者：Keith S. Barbato、Yi Luan、Daniele Ramella、James S. Panek、Scott E. Schaus

  DOI：10.1021/acs.orglett.5b02954

  日期：2015.12.4

  Chiral diols and biphenols catalyze the multicomponent condensation reaction of phenols, aldehydes, and alkenyl or aryl boronates. The condensation products are formed in good yields and enantioselectivities. The reaction proceeds via an initial Friedel–Crafts alkylation of the aldehyde and phenol to yield an ortho-quinone methide that undergoes an enantioselective boronate addition. A cyclization

  手性二醇和联苯酚催化酚、醛和烯基或芳基硼酸酯的多组分缩合反应。缩合产物以良好的产率和对映选择性形成。该反应通过醛和苯酚的初始弗里德尔-克来福特烷基化进行，产生邻醌甲基化物，然后进行对映选择性硼酸酯加成。在探索提供手性 2,4-二芳基苯并二氢吡喃产物的反应范围时发现了环化途径，其核心是天然产物中发现的结构基序。
• Facile Synthesis of Iodonium Salts by Reaction of Organotrifluoroborates with <i>p</i>-Iodotoluene Difluoride
  作者：Masanori Yoshida、Kanako Osafune、Shoji Hara

  DOI：10.1055/s-2007-966031

  日期：——

  A simple and easy method for the synthesis of various iodonium salts was developed, and involves the reaction of potassium organotrifluoroborates with P-iodotoluene difluoride under mild conditions. The one-pot synthesis of a ( Z)-(2-fluoroalkenyl)iodo-nium salt from an alkynyltrifluoroborate was also carried out.

  开发了一种简单易行的合成各种碘鎓盐的方法，包括有机三氟硼酸钾与对碘甲苯二氟化物在温和条件下的反应。还进行了由炔基三氟硼酸盐一锅法合成(Z)-(2-氟烯基)碘鎓盐。
• A stereoselective synthesis of γδ-unsaturated ketones possessing perfluoroalkyl groups by trifluoroborane etherate mediated 1,4-addition reaction of alkenyldiisopropoxyboranes to α,β-unsaturated ketones
  作者：Ei-ichi Takada、Shoji Hara、Akira Suzuki

  DOI：10.1016/s0040-4039(00)61600-3

  日期：1993.10

  A variety of γ,δ-unsaturated ketones (3,5, and 7) having perfluoroalkyl groups were prepared stereoselectively by the trifluoroborane etherate mediated 1,4-addition reaction of alkenyldiisopropoxyboranes (1) to α,β-unsaturated ketones substituted by perfluoroalkyl group (2,4, and 6). The undesired 1,2-addition of alkenyl groups or elimination of metal fluoride from the adducts could be avoided completely

  各种γ的，δ不饱和酮（3，5，和7）具有全氟烷基的被立体选择性地制备由alkenyldiisopropoxyboranes的三氟硼烷醚化物介导的1,4-加成反应（1）与α，由全氟烷基取代的β不饱和酮（2，4，和6）。可以完全避免不希望的烯基的1,2-加成或从加合物中消除金属氟化物，从而以高收率获得了产物。
• Organoboranes. 56. Systematic study of the reactions of 1-alkenylboronic esters with representative organolithium and Grignard reagents to provide an efficient, selective synthesis of organyl-1-alkenylborinic esters
  作者：Herbert C. Brown、Nagarajan Vasumathi、Navalkishore N. Joshi

  DOI：10.1021/om00028a021

  日期：1993.4

  A selective reaction of the ''ate'' complexes formed with 1-alkenylboronic esters and organolithium or Grignard reagents, by treatment with either Bronsted or Lewis acids at -78-degrees-C to give the corresponding organylalkenylborinic esters, is explored in this study. This systematic, detailed study reveals that the nature of the alkoxy group on boron, the nature and the amount of the alkyllithium or Grignard reagent used, the solvent, the reaction temperature, and the nature and amount of the acid used all play significant roles in influencing both the yield and the selectivity achieved for the formation of the desired organylalkenylborinates. Optimized procedures for the syntheses of representative organylalkenylborinic esters in high yield are summarized.
• Alkenylboronate Tethered Intramolecular Diels−Alder Reactions
  作者：Robert A. Batey、Avinash N. Thadani、Alan J. Lough

  DOI：10.1021/ja9828004

  日期：1999.1.1