((Z)-2-Bromo-1-hexenyl)diisopropoxyborane | 127611-65-8

• 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: ((Z)-2-Bromo-1-hexenyl)diisopropoxyborane
• 英文别名: [(Z)-2-bromo-hex-1-enyl]-diisopropoxy-borane；[(Z)-2-bromohex-1-enyl]-di(propan-2-yloxy)borane
• CAS: 127611-65-8
• 化学式: C₁₂H₂₄BBrO₂
• 分子量: 291.036
• InChiKey: QOZLMXMXQYNSDF-XFXZXTDPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.33
• 重原子数：
  16
• 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：

  ((Z)-2-Bromo-1-hexenyl)diisopropoxyborane 在 三氟化硼乙醚 、 lithium diisopropyl amide 作用下， 以 二氯甲烷 为溶剂， 反应 51.0h， 生成 ethyl (Z)-5-bromo-3-methyl-2-methylidenenon-4-enoate
  参考文献：
  名称：

  BF³Etherate Mediated 1,4-Addition Reaction of (1-Alkenyl)dialkoxyboranes to α-Acyl-α,β-unsaturated Esters

  摘要：

  In the, presence of BF3 etherate, (1-alkenyl)dialkoxyboranes react with alpha-acyl-alpha,beta-unsaturated esters to give alpha-acyl-gamma,delta-unsaturated esters in good yields.

  DOI：

  10.1080/00397919208021652

文献信息

• 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。
• Synthesis of Functionalized Allylsilicone Compounds via Rhodium-Catalyzed Conjugate Addition of (E)- or (Z)-[3-Trimethylsilyl-1-propenyl]boronic Acids to Enones
  作者：Yasunori Yamamoto、Masayoshi Fujita、Norio Miyaura

  DOI：10.1055/s-2002-25371

  日期：——

  The rhodium-catalyzed conjugate addition of (E)-Me 3 SiCH 2 CH=CHB(iPrO) 2 or (Z)-Me 3 SiCH 2 (C 4 H 9 )C=CHB(iPrO) 2 to enones provided a novel method for the synthesis of allylsilicone compounds possessing a carbonyl group inthe same molecule, which are versatile intermediates for intramolecular allylsilylation, giving cyclobutanols on treatment with Bu 4 NF.

  (E)-Me 3 SiCH 2 CH=CHB(iPrO) 2 或(Z)-Me 3 SiCH 2 (C 4 H 9 )C=CHB(iPrO) 2 与烯酮的铑催化共轭加成提供了一种新方法用于合成在同一分子中具有羰基的烯丙基硅氧烷化合物，这些化合物是分子内烯丙基甲硅烷基化的通用中间体，用 Bu 4 NF 处理得到环丁醇。
• Stereospecific Synthesis of Vinyl(phenyl)iodonium Tetrafluoroborates via Boron-Iodane Exchange of Vinylboronic Acids and Esters with Hypervalent Phenyliodanes
  作者：Masahito Ochiai、Mika Toyonari、Takema Nagaoka、Da-Wei Chen、Michio Kida

  DOI：10.1016/s0040-4039(97)01571-2

  日期：1997.9

  Reaction of vinylboronic acids and esters with hypervalent phenyliodanes in the presence of BF3-Et2O undergoes boron-iodane exchange at O degrees C in dichloromethane yielding vinyl(phenyl)iodonium tetrafluoroborates stereoselectively with retention of configuration. (C) 1997 Elsevier Science Ltd.
• Bf3 etherate mediated 1,4-addition of 1-alkenyldialkoxyboranes to α,β-unsaturated ketones. A stereoselective synthesis of γ, δ-Unsaturated ketones
  作者：Shoji Hara、Satoshi Hyuga、Masataka Aoyama、Michihiko Sato、Akira Suzuki

  DOI：10.1016/s0040-4039(00)94383-1

  日期：1990.1
• BF³Etherate Mediated 1,4-Addition Reaction of (1-Alkenyl)dialkoxyboranes to α-Acyl-α,β-unsaturated Esters
  作者：Masataka Aoyama、Shoji Hara、Akira Suzuki

  DOI：10.1080/00397919208021652

  日期：1992.9

  In the, presence of BF3 etherate, (1-alkenyl)dialkoxyboranes react with alpha-acyl-alpha,beta-unsaturated esters to give alpha-acyl-gamma,delta-unsaturated esters in good yields.