9-allyl-9-bora-bicyclo[3.3.1]nonane | 53317-08-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 金属杂环化合物
• 英文名称: 9-allyl-9-bora-bicyclo[3.3.1]nonane
• 英文别名: allyl-9-borabicyclo[3.3.1]nonane；B-allyl-9-borabicyclo[3.3.1]nonane；B-allyl-9-BBN；B-allyl-9-borabicyclononane；9-Borabicyclo[3.3.1]nonane, 9-(2-propenyl)-；9-prop-2-enyl-9-borabicyclo[3.3.1]nonane
• CAS: 53317-08-1
• 化学式: C₁₁H₁₉B
• 分子量: 162.083
• InChiKey: VWDZBSSQLJNTMJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.78
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 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：

  9-allyl-9-bora-bicyclo[3.3.1]nonane 、 異丙基三級丁基酮 生成 3-isopropyl-2,2-dimethyl-hex-5-en-3-ol
  参考文献：
  名称：

  Organoboranes. 20. The facile allylboration of representative carbonyl compounds with B-allyl derivatives of 9-borabicyclo[3.3.1]nonane

  摘要：

  DOI：

  10.1021/jo00433a022
• 作为产物：
  描述：

  9-硼双环[3.3.1]壬烷 以 四氢呋喃 为溶剂， 150.0 ℃ 、399.97 Pa 条件下， 反应 12.75h， 生成 9-allyl-9-bora-bicyclo[3.3.1]nonane
  参考文献：
  名称：

  A versatile synthesis of 9-BBN derivatives from organometallic reagents and 9-(triisopropylsilyl)thio-9-borabicyclo[3.3.1]nonane

  摘要：

  Representative B-substituted-9-BBNs (3) are efficiently prepared from either organolithium or Grignard reagents through their addition to (TIPS)S-9-BBN (1) which is readily available from TIPSSH and 9-BBN-H. The thermally induced collapse of the intermediate 'ate' complexes (2) produces 3 which is easily isolated in good yield and high purity. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00450-0

文献信息

• PEPTIDE TURN MIMETICS
  申请人：Cassidy Peter Joseph

  公开号：US20110040087A1

  公开（公告）日：2011-02-17

  Peptide mimetics of structure X herein which (i) provide a wide range of sidechain functions at all sidechain positions, (ii) can be incorporated in a peptide sequence, (iii) can be readily synthesized and (iv) have a variety of conformations. There is also provided a novel process which can provide valuable intermediates in relation to production of peptide mimetics of structure X which intermediates have a high degree of chemo- and stereo-selectivity. Preferred mimetics include structures I, II, III, IV, V and VI.

  本文中的结构X的肽类拟体具有以下特点：(i) 在所有侧链位置提供广泛的侧链功能，(ii) 可以被纳入肽序列中，(iii) 可以被轻松合成，(iv) 具有多种构象。还提供了一种新的过程，可以提供与结构X的肽类拟体的生产相关的有价值的中间体，这些中间体具有高度的化学和立体选择性。首选的拟体包括结构I、II、III、IV、V和VI。
• Indium(<scp>i</scp>)-catalyzed alkyl–allyl coupling between ethers and an allylborane
  作者：Hai Thanh Dao、Uwe Schneider、Shū Kobayashi

  DOI：10.1039/c0cc03673k

  日期：——

  An efficient method for alkyl–allyl cross-coupling between ethers and a 9-BBN-derived allylborane catalyzed by indium(I) triflate has been developed. The allylborane proved to be essential to obtain the desired products in high yields. The reaction displayed good substrate scope including high functional group tolerance.

  开发了一种高效的方法，用于通过三氟甲磺酸铟（I）催化的乙醚与9-BBN衍生烯丙基硼烷之间的烷基-烯丙基交联偶联反应。实验证明，烯丙基硼烷对于以高产率获得所需产物至关重要。该反应表现出良好的底物范围，包括对多种官能团的高容忍度。
• Total Synthesis of (−)-Salicylihalamide
  作者：Alois Fürstner、Thorsten Dierkes、Oliver R. Thiel、Gaetano Blanda

  DOI：10.1002/1521-3765(20011217)7:24<5286::aid-chem5286>3.0.co;2-g

  日期：2001.12.17

  the catalyst which bears an imidazol-2-ylidene ligand. The EIZ ratio obtained in this macrocyclization reaction was determined by the protecting groups at the remote phenolic OH group of the cyclization precursor. The elaboration of the resulting cycloalkene 37 into the final target involved a CrCl2-mediated synthesis of vinyliodide 49 which, after deprotection, did undergo a copper-catalyzed cross-coupling

  据报告，有效的细胞毒性海洋天然产物水杨酰卤酰胺A和B的简明全合成（Ia，B）。我们方法的关键步骤是[[（（S）-BINAP）Ru-Cl2] 2催化的β-酮酯18和32的不对称氢化反应。NEt 3和大环内酯核的环化反应通过使用“第二代”钌卡宾配合物24作为带有咪唑-2-亚甲基配体的催化剂通过闭环烯烃复分解（RCM）进行。在该大环化反应中获得的EIZ比率由环化前体的远端酚羟基上的保护基确定。将生成的环烯烃37精制为最终靶标涉及CrCl2介导的碘乙烯49的合成，该保护基在脱保护后确实经过了铜催化的与（Z，
• Radical Allylation, Vinylation, Alkynylation, and Phenylation Reactions of α-Halo Carbonyl Compounds with Organoboron, Organogallium, and Organoindium Reagents
  作者：Koichiro Oshima、Kazuaki Takami、Shin-ichi Usugi、Hideki Yorimitsu

  DOI：10.1055/s-2005-861846

  日期：——

  reactions of α-halo carbonyl compounds with alkenylindium proceeded via a radical process in the presence of triethylborane. Unactivated alkene moieties and styryl groups were introduced by this method. The carbon-carbon double bond geometry of the alkenylindiums was retained during the alkenylation. Preparation of an alkenylindium via a hydroindation of 1-alkyne and subsequent radical alkenylation established

  发现烯丙基镓和铟试剂可介导 α-碘或 α-溴羰基化合物的自由基烯丙基化反应。在三乙基硼烷的存在下，用由烯丙基氯化镁和三氯化镓制备的烯丙基镓处理溴乙酸苄酯，以极好的收率提供了4-戊烯酸苄酯。添加水作为助溶剂提高了烯丙基化产物的产率。烯丙基铟试剂也是有用的并且可以代替镓试剂。二烯丙基硼烷试剂可以以良好的产率烯丙基化 α-碘酯。在三乙基硼烷存在下，α-卤代羰基化合物与烯基铟的烯基化反应通过自由基过程进行。通过该方法引入了未活化的烯烃部分和苯乙烯基。烯基化过程中保留了烯基铟的碳-碳双键几何结构。通过 1-炔烃的氢化和随后的自由基烯基化制备烯基铟建立了一种有效的一锅法。本文公开了用有机铟试剂进行的自由基炔基化和苯基化。
• Allylic organometallic way to control acyclic stereochemistry and its application to the synthesis of carbohydrates
  作者：Yoshinori Yamamoto、Toshiaki Komatsu、Kazuhiro Maruyama

  DOI：10.1016/0022-328x(85)87354-x

  日期：1985.4

  The Cram/anti-Cram selectivity in the reactions of allylmetals with aldehydes and the erythro/threo selectivity in the reactions of substituted allylic organometallic compounds with other aldehydes can be controlled by the metal (M). Based on both selectivities, we can predict the diastereofacial selectivity of more complex systems. Finally, 1-O-methyl-2,6-dideoxyhexose and 1-O,3-O-dimethyl-4,6-dideoxyhexose

  烯丙基金属与醛的反应中的Cram / anti-Cram选择性和取代的烯丙基有机金属化合物与其他醛的反应中的赤/苏选择性可以通过金属（M）控制。基于这两种选择性，我们可以预测更复杂系统的非对面选择性。最后，制备1-O-甲基-2,6-二脱氧己糖和1-O，3-O-二甲基-4,6-二脱氧己糖。