(E)-2-(1-hexenyl)-1,3,2-dioxaborinane | 91083-28-2

• 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)-2-(1-hexenyl)-1,3,2-dioxaborinane
• 英文别名: B-(E)-1-hexenyl-1,3,2-dioxaborinane；2-[(E)-hex-1-enyl]-1,3,2-dioxaborinane
• CAS: 91083-28-2
• 化学式: C₉H₁₇BO₂
• 分子量: 168.044
• InChiKey: UJVULROINSNAJA-FNORWQNLSA-N

物化性质

• 沸点：
  194.1±23.0 °C(Predicted)
• 密度：
  0.89±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 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)-3-碘丙烯酸甲酯 、 (E)-2-(1-hexenyl)-1,3,2-dioxaborinane 在 palladium diacetate 、 trisodium tris(3-sulfophenyl)phosphine 二异丙胺 作用下， 以 水 、 乙腈 为溶剂， 以80%的产率得到(2Z,4E)-methyl nona-2,4-dienoate
  参考文献：
  名称：

  使用钯水溶性催化剂的铃木型交叉偶联反应。官能化二烯的合成

  摘要：

  在有机碱存在下用水溶性催化剂进行的硼酸或酯的钯（0）催化交叉偶联可以在温和条件下生产官能化的二烯。（60–90％的收率）。

  DOI：

  10.1016/0040-4039(95)00026-9
• 作为产物：
  描述：

  1-三甲基硅烷-1-己炔 以 水 为溶剂， 生成 (E)-2-(1-hexenyl)-1,3,2-dioxaborinane
  参考文献：
  名称：

  Simple procedures for the preparation of (Z)-2-(1-trimethylsilyl-1-alkenyl)-1,3,2-dioxaborinanes

  摘要：

  Two simple procedures for obtaining (Z)-2-(1-trimethylsilyl-1-alkenyl)-1,3,2-dioxaborinanes based on 1-trimethylsilyl-1-alkynes are described. In the first procedure, 1-trimethylsilyl-1-alkynes are hydroborated with diisopinocampheylborane to provide the corresponding (Z)-2-(trimethylsily1-1-alkenyl)-diisopinocampheylboranes. These are then reacted with excess acetaldehyde to afford the corresponding (2)-2-(1-trimethylsilyl-1-alkenyl)-diethoxyboranes which are esterified with 1,3-propane diol to give the (2)-2-(1-trimethylsilyl-1-alkenyl)-1,3,2-dioxaborinanes in good yields and in high stereochemical purities. In the second procedure, 1-trimethylsilyl-1-alkynes are hydroborated with dichloroborane-methyl sulfide complex in the presence of a stoichiometric amount of boron trichloride in hexane, followed by treatment with 1,3-propane diol. These novel stereodefined gem-alkenyldimetaliic compounds containing boron and silicon are isolated and characterized by NMR (H-1 and C-13) spectral data. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01405-2

文献信息

• Inter- and Intramolecular Additions of 1-Alkenylboronic Acids or Esters to Aldehydes and Ketones Catalyzed by Rhodium(I) Complexes in Basic, Aqueous Solutions
  作者：Norio Miyaura、Akinori Takezawa、Kenji Yamaguchi、Toshimichi Ohmura、Yasunori Yamamoto

  DOI：10.1055/s-2002-34219

  日期：——

  Grignard-type addition reaction of 1-alkenylboronic acids or their esters to aldehydes or ketones were carried out in aqueous MeOH or DME in the presence of KOH ( 1 equivalent) and an RhCl(dppf) or Rh(OH)(dppf) catalyst (3 mol%). The utility of the protocol was demonstrated in the corresponding intramolecular reaction giving cyclic homoallylic alcohols.

  在 KOH（1 当量）和 RhCl(dppf) 或 Rh(OH)(dppf) 催化剂存在下，在 MeOH 或 DME 水溶液中进行 1-烯基硼酸或其酯与醛或酮的格氏型加成反应（ 3 摩尔％）。该协议的效用在相应的分子内反应中得到了证明，给出了环状 homoallylic 醇。
• Novel diastereoselective synthesis of (E)- and (Z)-allylsilanes via organoboranes
  作者：Narayan G. Bhat、Wendy C. Lai、Matthew B. Carroll

  DOI：10.1016/j.tetlet.2007.04.052

  日期：2007.6

  A simple, novel diastereoselective synthesis of both (E)- and (Z)-allylsilanes via organoboranes is developed. (E)-1-Alkenylboronate esters easily prepared from the corresponding terminal alkynes via hydroboration with dibromoborane-methyl sulfide complex followed by treatment with 1,3-propane diol readily react with trimethylsilylmethyllithium at −78 °C in methanol followed by reaction with iodine

  通过有机硼烷开发了一种简单，新颖的非对映选择性合成（E）-和（Z）-烯丙基硅烷的方法。（E）-1-烯基硼酸酯很容易从相应的末端炔烃经二溴硼烷-甲基硫醚络合物加氢硼化制得，然后用1,3-丙二醇处理，很容易在-78°C下与三甲基甲硅烷基甲基锂在甲醇中反应，然后与碘反应。甲醇以高收率（72–80％）和高立体化学纯度（CMR光谱数据证明为98％）生产相应的（Z）-烯丙基硅烷。同样，（Z）-1-烯基硼酸酯在甲醇中于-78°C与三甲基甲硅烷基甲基锂反应，然后在甲醇中用碘处理，以适度收率（57-65％）以高立体化学纯度（大于98％生成）生成相应的（E）-烯丙基硅烷通过CMR光谱数据显示）。
• First example of a stable 1,1-bidentate Lewis acid based on boron and zirconium: synthesis, reactivity, X-ray analysis and NMR studies
  作者：Ewa Skrzypczak-Jankun、Bruce V. Cheesman、Bin Zheng、Richard M. Lemert、Siddharta Asthana、Morris Srebnik

  DOI：10.1039/c39940000127

  日期：——

  Chlorobis(cyclopentadienyl)[1-(1,3,2-dioxaborinane-2-yl)hexyl]zirconium(IV)2, fully characterized by X-ray, 1H–1H double-quantum-filtered COSY and 13C-1H heteronuclear chemical shift correlation NMR studies, IR and elemental analysis, reacts selectively with electrophilic reagents, N-bromo- and N-chlorosuccinimide and bromine to give α-halobronic esters; it also polymerizes styrene without the aid

  氯双（环戊二烯基）[1-（1,3,2-二氧杂硼烷-2-基）己基]锆（IV）2，充分表征通过X射线，1 H- 1 H ^双量子过滤COZY和13 C- 1 H异核化学位移相关NMR研究，红外光谱和元素分析，与亲电子试剂，N-溴和N-氯代琥珀酰亚胺和溴选择性反应，生成α-卤代硼酸酯；它也可以在不借助助催化剂的情况下聚合苯乙烯。
• Enantioselective addition of alkenylzinc reagents to aldehydes with organoboronates as the alkenyl source
  作者：Zhuo Chai、Xin-Yuan Liu、Jun-Kang Zhang、Gang Zhao

  DOI：10.1016/j.tetasy.2007.02.026

  日期：2007.4

  Alkenylboronates were used as a vinyl source in the asymmetric addition of an alkenylzinc reagent to aldehydes catalyzed by a dendritic ligand. The resulting allylic alcohol products were obtained in 66–96% ee and 35–64% yields.

  在烯基锌试剂不对称加成由树状配体催化的醛中时，烯基硼酸酯用作乙烯基源。所得的烯丙醇产品以ee 66-96％和35-64％的产率获得。
• 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.