4-ClC6H4-9-BBN

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-ClC6H4-9-BBN
• 英文别名: 9-(4-Chlorophenyl)-9-borabicyclo[3.3.1]nonane
• 化学式: C₁₄H₁₈BCl
• 分子量: 232.561
• InChiKey: DNXFVUDRDDDWRR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.15
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  4-ClC6H4-9-BBN 、 2'-cyanocinnamic acid methyl ester 在 methoxy(cyclooctadiene)rhodium(I) dimer 作用下， 以 甲苯 为溶剂， 以88%的产率得到
  参考文献：
  名称：

  共轭加成有机硼促使氰基取代的不饱和酯发生环化反应。

  摘要：

  [反应：见正文]具有氰基侧基的不饱和酯在铑（I）催化剂存在下与B-Ar-9-BBNs反应，以高收率得到五元和六元β-烯胺酯。通过初始共轭加成Ar-铑（I）物种而形成的（oxa-pi-烯丙基）铑（I）中间体经过快速的分子内加成至氰基，以构建碳环骨架。

  DOI：

  10.1021/ol062882y
• 作为产物：
  描述：

  4-氯苯基溴化镁 、 8-甲氧基-9-硼杂双环[3.3.1]壬烷 以 正己烷 为溶剂， 生成 4-ClC6H4-9-BBN
  参考文献：
  名称：

  Stereoselective Suzuki Coupling Reaction of an α-Bromo-α-fluoro-β-lactam

  摘要：

  A new strategy has been developed for the synthesis of alpha-aryl-alpha-fluoro-beta-lactams via the Suzuki cross-coupling of alpha-bromo-alpha-fluoro-beta-lactam with a range of different aryl-(9-BBN) reagents. This method provides facile access to multisubstituted alpha-fluoro-beta-lactams in a diastereoselective manner. The synthetic utility of alpha-bromo-alpha-fluoro-beta-lactam has been demonstrated by the arylation of alpha-bromo-alpha-fluoro-beta-lactam.

  DOI：

  10.1055/s-0034-1379637

文献信息

• Stereoselective Synthesis of (<i>E</i>)-(Trisubstituted alkenyl)borinic Esters: Stereochemistry Reversed by Ligand in the Palladium-Catalyzed Reaction of Alkynylborates with Aryl Halides
  作者：Naoki Ishida、Yasuhiro Shimamoto、Masahiro Murakami

  DOI：10.1021/ol902278q

  日期：2009.12.3

  The palladium-catalyzed reaction of alkynylborates with aryl halides stereoselectively gave (E)-(trisubstituted alkenyl)-9-BBNs, in which two different aryl groups were installed trans to each other.

  炔基硼酸酯与芳基卤化物的钯催化反应立体选择性地得到（E）-（三取代的烯基）-9-BBN，其中两个不同的芳基彼此反式安装。
• Stereoselective Suzuki Coupling Reaction of an α-Bromo-α-fluoro-β-lactam
  作者：Akira Ando、Atsushi Tarui、Erina Miyata、Ayumi Tanaka、Kazuyuki Sato、Masaaki Omote

  DOI：10.1055/s-0034-1379637

  日期：——

  A new strategy has been developed for the synthesis of alpha-aryl-alpha-fluoro-beta-lactams via the Suzuki cross-coupling of alpha-bromo-alpha-fluoro-beta-lactam with a range of different aryl-(9-BBN) reagents. This method provides facile access to multisubstituted alpha-fluoro-beta-lactams in a diastereoselective manner. The synthetic utility of alpha-bromo-alpha-fluoro-beta-lactam has been demonstrated by the arylation of alpha-bromo-alpha-fluoro-beta-lactam.
• Cyclization Reaction of Cyano-Substituted Unsaturated Esters Prompted by Conjugate Addition of Organoborons
  作者：Tomoya Miura、Tatsuro Harumashi、Masahiro Murakami

  DOI：10.1021/ol062882y

  日期：2007.3.1

  [reaction: see text] Unsaturated esters possessing a pendent cyano moiety react with B-Ar-9-BBNs in the presence of a rhodium(I) catalyst to give the five- and six-membered beta-enamino esters in good yield. An (oxa-pi-allyl)rhodium(I) intermediate, formed by initial conjugate addition of an Ar-rhodium(I) species, undergoes a facile intramolecular addition to the cyano group to construct the carbocyclic

  [反应：见正文]具有氰基侧基的不饱和酯在铑（I）催化剂存在下与B-Ar-9-BBNs反应，以高收率得到五元和六元β-烯胺酯。通过初始共轭加成Ar-铑（I）物种而形成的（oxa-pi-烯丙基）铑（I）中间体经过快速的分子内加成至氰基，以构建碳环骨架。