(R)-alpine borane | 64106-79-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (R)-alpine borane
• 英文别名: R-Alpine-Borane;B-Isopinocampheyl-9-borabicyclo[3.3.1]nonane；9-[(1R,2S,3R,5R)-2,6,6-trimethyl-3-bicyclo[3.1.1]heptanyl]-9-borabicyclo[3.3.1]nonane
• CAS: 64106-79-2
• 化学式: C₁₈H₃₁B
• 分子量: 258.255
• InChiKey: VCDGSBJCRYTLNU-CJGYBVCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.66
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  5.0
• 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：

  二甲基(氯甲基)丙烯酯 、 (R)-alpine borane 在 正丁基锂 、 水 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 为溶剂， 反应 2.0h， 以83%的产率得到diethyl (cyclooctylmethyl)phosphonate
  参考文献：
  名称：

  有机磷化合物的温和合成：含磷卡宾与有机硼烷的反应。

  摘要：

  有机硼烷在温和条件下与含磷类卡宾反应生成多种功能化的有机磷化合物。在某些情况下，可以观察到与硼相连的一组选择性迁移。次膦酸酯-硼烷复合物被引入作为合成次膦酸酯的新型合成子。

  DOI：

  10.1021/ol800085u
• 作为产物：
  描述：

  (+)-α-蒎烯 、 alkaline earth salt of/the/ methylsulfuric acid 以 四氢呋喃 为溶剂， 反应 24.0h， 以98%的产率得到(R)-alpine borane
  参考文献：
  名称：

  Hydroboration. 94. Rates of Hydroboration of 2-Organylapopinenes with 9-Borabicyclo[3.3.1]nonane, Providing B-(2-Organylapoisopinocampheyl)-9-borabicyclo[3.3.1]nonanes, Potentially Valuable for the Asymmetric Reduction of Prochiral Ketones

  摘要：

  Five representative enantiomerically pure, hindered terpenes, derived from a-pinene, namely 8-organylapopinenes (2-R-apopinenes, R = Et, Pr, i-Bu, Ph, and i-Pr) have been treated with 9-borabicyclo[3.3.1]nonane (9-BBN) in a 1:1 molar ratio in THF at 24 degrees C and the rate of hydroboration followed. Increasing the bulk of the 2-R group from the 2-methyl of alpha-pinene (Ipc, 2-methylapopinene) to 8-ethyl-(Eap), to 2-propyl-(Prap), to 2-isobutyl-(i-Bap), to 2-phenyl-(Pap), and to 2-isopropyl-(i-Prap) significantly lowers the rate of hydroboration with 9-BBN. Thus, the rate of hydroboration of alpha-pinene with 9-BBN is faster than the rates for the 2-R-apopinenes studied. The sterically bulkier 2-isobutyl-, 2-phenyl-, and 2-isopropylapopinenes reveal a significantly slower rate of hydroboration with 9-BBN. At an elevated temperature, 65 degrees C, the reaction of 9-BBN (1.0 equiv) with a slight excess of optically pure 2-isobutyl- and 2-phenylapopinenes (1.10-1.20 equiv), under neat conditions, is facilitated to provide the desired B-(2-organylapoisopinocampheyl)-9-borabicyclo[3.3.1]nonanes (2-organyl = isobutyl- and phenyl) in quantitative yield. Unfortunately, this synthesis failed for 2-isopropylapopinene. Fortunately, an indirect synthesis proved satisfactory. Treatment of enantiomerically pure (2-isopropylapoisopinocampheyl)borane, i-PrapBH(2), conveniently synthesized from 2-isopropylapopinene, and 1,5-cyclooctadiene (1,5-COD), provided, after thermal isomerization, the desired 1:1 adduct [B-(2-Rap)-9-BBN; 2-Rap = 2-isopropylapoisopinyl skeleton] in quantitative yield. Consequently, five of the 2-R-apopinenes, R = Et, Pr, i-Bu, Ph, and i-Pr, have been successfully converted into the corresponding B-(2-Rap)-9-BBN derivatives.

  DOI：

  10.1021/jo9617169
• 作为试剂：
  描述：

  2-(1-bromoethyl)-6-fluoro-3-(3-fluorophenyl)-4H-chromen-4-one 在 草酰氯 、 偶氮二甲酸二异丙酯 、 potassium carbonate 、 二甲基亚砜 、 (R)-alpine borane 、 三苯基膦 、 正丁醇 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 27.83h， 生成 TGR-1202 、 (R)-2-(1-(4-amino-3-(3-fluoro-4-isopropoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-6-fluoro-3-(3-fluorophenyl)-4H-chromen-4-one
  参考文献：
  名称：

  Combination of Anti-CD20 Antibody and PI3 Kinase Selective Inhibitor

  摘要：

  本文提供了一种高效的化合物A（一种PI3Kδ选择性抑制剂）和抗CD20抗体的组合，用于治疗和改善由PI3Kδ和/或CD20介导的疾病和紊乱。特别是，该组合可用于治疗癌症和自身免疫疾病。更具体地说，本发明提供了一种化合物A或其立体异构体与ublituximab的组合，用于治疗和/或改善像白血病和淋巴瘤这样的血液恶性肿瘤。

  公开号：

  US20150290317A1

文献信息

• Modulation of airway inflammation in patients with cystic fibrosis and related diseases
  申请人：Karp L. Christopher

  公开号：US20050113443A1

  公开（公告）日：2005-05-26

  This invention provides a method for treating pulmonary disease in patients with cystic fibrosis, variant cystic fibrosis, and non-cystic fibrosis bronchiectasis. The method involves administering a pharmaceutically effective amount of a lipoxin or lipoxin analogue to subjects with cystic fibrosis or related disease, in amounts sufficient to downregulate harmful neutrophilic airway inflammatory responses.

  该发明提供了一种治疗囊性纤维化、变异性囊性纤维化和非囊性纤维化支气管扩张症患者肺部疾病的方法。该方法涉及向囊性纤维化或相关疾病的受试者投予药效有效量的脂氧素或脂氧素类似物，足以下调有害的中性粒细胞空气道炎症反应。
• Hydride transfer reactions of anionic metal formyl complexes: a mechanistic Test
  作者：J.A. Gladysz、James H. Merrifield

  DOI：10.1016/s0020-1693(00)88992-6

  日期：1978.1
• BROWN, HERBERT C.;PARK, WON SUH;CHO, BYUNG TAE;RAMACHANDRAN, P. VEERARAGH+, J. ORG. CHEM., 52,(1987) N 24, 5406-5412
  作者：BROWN, HERBERT C.、PARK, WON SUH、CHO, BYUNG TAE、RAMACHANDRAN, P. VEERARAGH+

  DOI：——

  日期：——
• Mild Synthesis of Organophosphorus Compounds:  Reaction of Phosphorus-Containing Carbenoids with Organoboranes
  作者：Monika I. Antczak、Jean-Luc Montchamp

  DOI：10.1021/ol800085u

  日期：2008.3.1

  Organoboranes react with phosphorus-containing carbenoids to produce a variety of functionalized organophosphorus compounds under mild conditions. In some cases, selective migration of one group attached to boron can be observed. Phosphonite-borane complexes are introduced as novel synthons for the synthesis of phosphinic esters.

  有机硼烷在温和条件下与含磷类卡宾反应生成多种功能化的有机磷化合物。在某些情况下，可以观察到与硼相连的一组选择性迁移。次膦酸酯-硼烷复合物被引入作为合成次膦酸酯的新型合成子。
• Hydroboration. 94. Rates of Hydroboration of 2-Organylapopinenes with 9-Borabicyclo[3.3.1]nonane, Providing <i>B</i>-(2-Organylapoisopinocampheyl)-9-borabicyclo[3.3.1]nonanes, Potentially Valuable for the Asymmetric Reduction of Prochiral Ketones
  作者：Ulhas P. Dhokte、Herbert C. Brown

  DOI：10.1021/jo9617169

  日期：1997.2.1

  Five representative enantiomerically pure, hindered terpenes, derived from a-pinene, namely 8-organylapopinenes (2-R-apopinenes, R = Et, Pr, i-Bu, Ph, and i-Pr) have been treated with 9-borabicyclo[3.3.1]nonane (9-BBN) in a 1:1 molar ratio in THF at 24 degrees C and the rate of hydroboration followed. Increasing the bulk of the 2-R group from the 2-methyl of alpha-pinene (Ipc, 2-methylapopinene) to 8-ethyl-(Eap), to 2-propyl-(Prap), to 2-isobutyl-(i-Bap), to 2-phenyl-(Pap), and to 2-isopropyl-(i-Prap) significantly lowers the rate of hydroboration with 9-BBN. Thus, the rate of hydroboration of alpha-pinene with 9-BBN is faster than the rates for the 2-R-apopinenes studied. The sterically bulkier 2-isobutyl-, 2-phenyl-, and 2-isopropylapopinenes reveal a significantly slower rate of hydroboration with 9-BBN. At an elevated temperature, 65 degrees C, the reaction of 9-BBN (1.0 equiv) with a slight excess of optically pure 2-isobutyl- and 2-phenylapopinenes (1.10-1.20 equiv), under neat conditions, is facilitated to provide the desired B-(2-organylapoisopinocampheyl)-9-borabicyclo[3.3.1]nonanes (2-organyl = isobutyl- and phenyl) in quantitative yield. Unfortunately, this synthesis failed for 2-isopropylapopinene. Fortunately, an indirect synthesis proved satisfactory. Treatment of enantiomerically pure (2-isopropylapoisopinocampheyl)borane, i-PrapBH(2), conveniently synthesized from 2-isopropylapopinene, and 1,5-cyclooctadiene (1,5-COD), provided, after thermal isomerization, the desired 1:1 adduct [B-(2-Rap)-9-BBN; 2-Rap = 2-isopropylapoisopinyl skeleton] in quantitative yield. Consequently, five of the 2-R-apopinenes, R = Et, Pr, i-Bu, Ph, and i-Pr, have been successfully converted into the corresponding B-(2-Rap)-9-BBN derivatives.