B-cyclopentyl-9-borabicyclo[3.3.1]nonane | 49623-12-3

• 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: B-cyclopentyl-9-borabicyclo[3.3.1]nonane
• 英文别名: 9-cyclopentyl-9-bora-bicyclo[3.3.1]nonane；9-Cyclopentyl-9-bora-bicyclo<3.3.1>nonan；B-Cyclopentyl-9-bora-bicyclo<3.3.1>nonan；9-Cyclopentyl-9-borabicyclo<3.3.1>nonan；B-Cyclopentyl-9-borabicyclo<3.3.1>nonan；9-Cyclopentyl-9-borabicyclo[3.3.1]nonane
• CAS: 49623-12-3
• 化学式: C₁₃H₂₃B
• 分子量: 190.137
• InChiKey: HXTQJCZEZWVIIE-UHFFFAOYSA-N

物化性质

• 沸点：
  274.5±7.0 °C(Predicted)
• 密度：
  0.90±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.53
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  B-cyclopentyl-9-borabicyclo[3.3.1]nonane 在 2,6-二叔丁基苯酚 、 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 生成 dicyclopentyl-acetonitrile
  参考文献：
  名称：

  Reaction of organoboranes with dichloroacetonitrile under the influence of potassium 2,6-di-tert-butylphenoxide. A convenient general procedure for the preparation of .alpha.-chloro nitriles and dialkylacetonitriles

  摘要：

  DOI：

  10.1021/ja00722a070
• 作为产物：
  描述：

  8-甲氧基-9-硼杂双环[3.3.1]壬烷 、 环戊烯 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 B-cyclopentyl-9-borabicyclo[3.3.1]nonane
  参考文献：
  名称：

  Solid-phase synthesis of unnatural α-amino acid derivatives using a resin-bound glycine cation equivalent

  摘要：

  Unnatural amino acids were synthesized on solid-phase by reaction of a resin-bound Schiff base with organoboranes. This novel use of a resin-bound glycine cation equivalent allows for the preparation of a variety of amino acid structural types not readily available by the complementary anionic equivalent. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01101-6

文献信息

• Reaction of Unstabilized Iodonium Ylides with Organoboranes
  作者：Masahito Ochiai、Yoshimi Tuchimoto、Nobuyuki Higashiura

  DOI：10.1021/ol0495669

  日期：2004.4.1

  [reaction: see text] Exposure of monocarbonyl iodonium ylides, generated by the ester exchange of (Z)-(2-acetoxyvinyl)-lambda(3)-iodanes with EtOLi, to organoboranes results in a 1,2-shift of a carbon ligand from boron to the ylide carbons, which probably generates hitherto uncharacterized alpha-boryl ketones.

  [反应：请参阅文本]通过（Z）-（2-乙酰氧基乙烯基）-λ（3）-碘酮与EtOLi的酯交换产生的单羰基碘鎓烷基化物暴露于有机硼烷会导致碳的1,2-转移从硼到内含碳的配体，可能会产生迄今未表征的α-硼基酮。
• The Enantioselective Synthesis of α-Amino Acid Derivatives via Organoboranes
  作者：Martin J. O'Donnell、Mark D. Drew、Jeremy T. Cooper、Francisca Delgado、Changyou Zhou

  DOI：10.1021/ja017522e

  日期：2002.8.1

  Optically active (S)-α-amino acids are prepared in 54−95% ee (12 cases) by reaction of the Schiff base acetate of glycine tert-butyl ester with B-alkyl-9-BBN derivatives in the presence of the Cinc...

  通过甘氨酸叔丁酯的席夫碱乙酸酯与 B-烷基-9-BBN 衍生物在 Cinc 存在下反应，以 54-95% ee（12 例）制备光学活性 (S)-α-氨基酸...
• Copper-Catalyzed γ-Selective and Stereospecific Allylic Cross-Coupling with Secondary Alkylboranes
  作者：Yuto Yasuda、Kazunori Nagao、Yoshinori Shido、Seiji Mori、Hirohisa Ohmiya、Masaya Sawamura

  DOI：10.1002/chem.201501055

  日期：2015.6.26

  of the copper‐catalyzed coupling reactions between organoboron compounds and allylic phosphates is expanded significantly by employing triphenylphosphine as a ligand for copper, allowing the use of secondary alkylboron compounds. The reaction proceeds with complete γ‐E‐selectivity and preferential 1,3‐syn stereoselectivity. The reaction of γ‐silicon‐substituted allylic phosphates affords enantioenriched

  通过使用三苯基膦作为铜的配体，有机硼化合物与烯丙基磷酸酯之间铜催化的偶联反应的范围大大扩展，从而允许使用仲烷基硼化合物。反应以完全的γ- E-选择性和优先的1,3-顺式立体选择性进行。γ-硅取代的烯丙基磷酸酯的反应可提供对映体富集的α-立体异构烯丙基硅烷。
• The synthesis of methoxycyclopropanes via the treatment of ate-complexes obtained from B-alkyl-9-borabicyclo[3,3,1]nonanes and lithium methoxyallene with acetic acid
  作者：Norio Miyaura、Tomohiro Yoshinari、Mitsuomi Itoh、Akira Suzuki

  DOI：10.1016/s0040-4039(01)85549-0

  日期：1980.1

  The reaction of acetic acid with ate-complexes prepared from B-alkyl-9-borabicyclo-[3,3,1]nonanes and 1-lithiol-1-methoxyallene gives corresponding 1-alkyl-1-methoxycyclopropanes in good yields.

  乙酸与由B-烷基-9-硼杂环-[3,3,1]壬烷和1-lithiol-1-甲氧基烯丙酸酯制得的配合物反应，可得到相应的1-烷基-1-甲氧基环丙烷。
• Addition compounds of alkali metal hydrides
  作者：Herbert C. Brown、Gary W. Kramer、John L. Hubbard、S. Krishnamurthy

  DOI：10.1016/s0022-328x(00)83693-1

  日期：1980.4

  The reaction of t-butyllithium with representative trialkylboranes possessing widely differing steric requirements was examined. This reaction occurs rapidly in ether solvents, even at −78°C, with formation of the corresponding lithium trialkylborohydride in quantitative yield. This synthesis is highly general, accomodating even strongly hindered trialkylboranes such as tris(trans-2-methylcyclopentyl)borane

  考察了叔丁基锂与具有广泛不同空间要求的代表性三烷基硼烷的反应。即使在-78℃下，该反应在醚溶剂中也迅速发生，并以定量收率形成相应的三烷基硼氢化锂。这种合成是高度通用的，甚至包含受强烈阻碍的三烷基硼烷，例如三（反-2-甲基环戊基）硼烷和三唾液酸基硼烷。唯一的副产物是异丁烯，其通常是无害的且易于除去。通过氢化物分析，红外光谱和11对三烷基硼氢化锂进行了表征B NMR谱。三烷基硼氢化物的形成似乎是由于动力学因素，而不是由于热力学因素。该反应为三烷基硼氢化锂提供了一种高度通用，简便且定量的途径。