(Z)-1-octenylboronic acid | 121021-30-5

• 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)-1-octenylboronic acid
• 英文别名: (1Z)-Oct-1-en-1-ylboronic acid；[(Z)-oct-1-enyl]boronic acid
• CAS: 121021-30-5
• 化学式: C₈H₁₇BO₂
• 分子量: 156.033
• InChiKey: RBTAJLKAPFBZDQ-FPLPWBNLSA-N

物化性质

• 沸点：
  263.2±23.0 °C(Predicted)
• 密度：
  0.911±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.52
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z)-1-octenylboronic acid 在 氯 作用下， 以 二氯甲烷 为溶剂， 以70%的产率得到(E)-1-chlorooct-1-ene
  参考文献：
  名称：

  Vinylic organoboranes. 14. A stereospecific synthesis of (E)-1-halo-1-alkenes from 1-alkynes

  摘要：

  DOI：

  10.1021/jo00287a019
• 作为产物：
  描述：

  1-bromo-1-octyne 、 dibromoborane-methyl sulfide complex 生成 (Z)-1-octenylboronic acid
  参考文献：
  名称：

  BROWN, HERBERT C.;HAMAOKA, TSUTOMU;RAVINDRAN, NAIR;SUBRAHMANYAM, CHITTI;S+, J. ORG. CHEM., 54,(1989) N6, C. 6075-6079

  摘要：

  DOI：

文献信息

• Pd-Catalyzed Arylation of 1,2-Amino Alcohol Derivatives via β-Carbon Elimination
  作者：Miquel A. Pericàs、Ruben Martin、Miriam Sau

  DOI：10.1055/a-1699-4766

  日期：2022.1

  AbstractHerein, we describe a Pd-catalyzed arylation of 1,2-amino alcohols with aryl halides enabled by a retroallylation manifold. This protocol constitutes a new entry point to β-arylated aldehydes via the intermediacy of in situ generated enamine intermediates. The protocol is characterized by its exquisite regioselectivity profile and broad substrate scope – including challenging substrate combinations

  摘要在此，我们描述了通过逆芳基化歧管实现的 1,2-氨基醇与芳基卤化物的 Pd 催化芳基化。该协议通过原位生成的烯胺中间体的中间体构成了 β-芳基化醛的新切入点。该协议的特点是其精细的区域选择性分布和广泛的底物范围 - 包括具有挑战性的底物组合 - 即使以对映选择性的方式也是如此。
• Catalyst-Controlled Regioselectivity in the Synthesis of Branched Conjugated Dienes via Aerobic Oxidative Heck Reactions
  作者：Changwu Zheng、Dian Wang、Shannon S. Stahl

  DOI：10.1021/ja307371w

  日期：2012.10.10

  Pd-catalyzed aerobic oxidative coupling of vinylboronic acids and electronically unbiased alkyl olefins provides regioselective access to 1,3-disubstituted conjugated dienes. Catalyst-controlled regioselectivity is achieved by using 2,9-dimethylphenanthroline as a ligand. The observed regioselectivity is opposite to that observed from a traditional (nonoxidative) Heck reaction between a vinyl bromide

  Pd 催化的乙烯基硼酸和电子无偏烷基烯烃的有氧氧化偶联提供了对 1,3-二取代共轭二烯的区域选择性访问。催化剂控制的区域选择性是通过使用 2,9-二甲基菲咯啉作为配体来实现的。观察到的区域选择性与从溴乙烯和烯烃之间的传统（非氧化）Heck 反应观察到的相反。DFT 计算研究表明，2,9-二甲基菲咯啉配体的空间效应促进了烯烃内部位置的 CC 键形成。
• Synthesis of Functionalized Vinyl Boronates via Ruthenium-Catalyzed Olefin Cross-Metathesis and Subsequent Conversion to Vinyl Halides
  作者：Christie Morrill、Robert H. Grubbs

  DOI：10.1021/jo0345345

  日期：2003.7.1

  using ruthenium-catalyzed olefin cross-metathesis of 1-propenyl pinacol boronate and various alkenes, including functionalized and 1,1-disubstituted alkenes. The resultant boronate cross products are stereoselectively transformed into predominantly Z-vinyl bromides and E-vinyl iodides. The vinyl bromides may be synthesized in a two-step, one-pot synthesis from a variety of olefins, resulting in a Z-selective

  适用于铃木交叉偶联反应的功能化乙烯基频哪醇硼酸酯是使用1-丙烯基频哪醇硼酸酯和各种烯烃（包括功能化和1,1-二取代的烯烃）经钌催化的烯烃交叉复分解合成的。将所得的硼酸酯交叉产物立体选择性地转化为主要的Z-乙烯基溴化物和E-乙烯基碘化物。乙烯基溴化物可以由多种烯烃以两步，一锅法合成来合成，从而导致Z选择性形式的乙烯基溴化物交叉复分解反应。
• Mild conversion of alkenyl boronic acids to alkenyl halides with halosuccinimides
  作者：Nicos A. Petasis、Ilia A. Zavialov

  DOI：10.1016/0040-4039(95)02262-7

  日期：1996.1

  Reaction of alkenyl boronic acids with halosuccinimides (NIS, NBS or NCS) gives the corresponding alkenyl halides with the same geometry. This method is suitable for the synthesis of geometrically pure (E) and (Z) alkenyl halides, as well as 1,1- and 1,2-dihaloalkenes.

  烯基硼酸与卤代琥珀酰亚胺（NIS，NBS或NCS）反应，得到相应的具有相同几何形状的烯基卤化物。该方法适用于合成几何上纯净的（E）和（Z）烯基卤化物，以及1,1-和1,2-二卤代烯烃。
• Improved Protein Kinase C Affinity through Final Step Diversification of a Simplified Salicylate-Derived Bryostatin Analog Scaffold
  作者：Paul A. Wender、Daryl Staveness

  DOI：10.1021/ol502492b

  日期：2014.10.3

  Bryostatin 1 an clinical trials or preclinical development for cancer, Alzheimer disease, and a first of-its-kind strategy for HIV/AIDS eradication, is neither readily available nor optimally suited for clinical use. In preceding work, we disclosed a new class of simplified bryostatin analogs designed for ease of access and tunable activity. Here we describe a final step diversification strategy that provides in only 25 synthetic steps, simplified and tunable analogs with bryostatin like PKC modulatory activities.